The 20 Best Five-year Runs In Rap

Someone once told me this amazing quote and they attributed it to Jay Z. I don’t actually know if Jay Z said it, but it’s still an amazing quote and a great point nonetheless. It went like this, “You’re more likely to be an all-star in the NBA than you are to have five good years in the rap game.” Think about that. There’s 24 NBA all-stars every year, there’s only 20 people on this list. And honestly, there could hardly even be a 21st person on this list. That’s nuts.

Yet, that’s how the game goes. Some of that has to do with rap being such a young genre. Hip-hop is only about 40 years old, not even old enough to be your grandpa. In recent years, rappers like Jay Z, Nas, and Eminem have found ways to remain relevant and productive in the later years of their careers. Hopefully, they've laid a foundation for future rappers to follow. But beyond rap, consider that even legendary artists like Jimi Hendrix only had about four years of mainstream exposure, and the three albums he released he released that changed rock music forever—1967's Are You Experienced & Axis: Bold as Love and 1968's Electric Ladyland—came out in an 18 month span.

Still, consider that even some of the dopest rappers around could barely string five consecutive quality years together. In 1992 and 1993, Snoop Dogg was the Best Rapper Alive. He was the main voice behind Dr. Dre’s The Chronic, and his album Doggystyle is a certified classic. He killed every song he touched. But by 1996? When he dropped his second album, Doggfather, he hit one of the worst sophomore slumps rap has ever seen. Just like that, it was gone. Thankfully, Snoop later returned to prominence but that doesn’t mean he didn’t stumble along the way.

That’s why five year runs are so important. Just ask The RZA, he built the Wu-Tang empire telling the rest of the crew, "I'm taking us to No. 1. Give me five years, and I promise that I'll get us there." For many of the greatest rappers ever, the large majority of the highlights in their career can be found in that brief window. A rapper’s prime rarely lasts longer than that. So we took a look at some of the Best 5 Year Rapper Runs (and presented them chronologically) to see which rappers really held it down for five summers...

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Rakim: 1986-1990

Solo Albums: n/a
Group Albums: Paid in Full (1987), Follow the Leader (1988), Let the Rhythm Hit 'Em (1990)
Biggest Hits: "Paid in Full" (1987), "Eric B. Is President" (1987), "I Know You Got Soul" (1987), "Microphone FIend" (1988), "Lyrics of Fury" (1988)

Here is something I wrote last year, on the 25th anniversary of the Eric B. & Rakim's 1987 debut album, Paid in Full. It's called, "Rakim is the most important MC in the history of rap music," and I think it speaks to Rakim's dominance in the first five years of his career.

It's still always weird to me to hear people argue about who's the best MC. This has to do my age, and the way that the things you think at certain points in your life crystalize into something more like objective truth than opinion. I was sixteen years old in 1987, and shortly after Paid In Full came out, there was simply no debating who was the best MC. The answer to that question was Rakim, period, the end. Everyone who listened to rap knew this. At least where I was from, in the suburbs an hour outside of New York City. I have since heard stories about how there was heavy argument and rivalry around that time in the city itself. Was Boogie Down Productions' KRS-One better? Was Big Daddy Kane better? Kool G Rap? Big Daddy Kane and KRS-One and Kool G Rap are phenomenally great rappers. And certainly, lots of people knew more about rap than my friends and I did in 1987 (and more about it than my friends and I do now.) But for us, in the halls of Red Bank Regional High School in New Jersey, it was not up for discussion: Rakim was the best.




My opinion has changed over the years: I now say that Biggie Smalls is the best rapper ever. (While Jay-Z is the "greatest" rapper ever, and Ghostface Killah is my "favorite." I am a nudnik who gets hung up on semantics.) But my first reaction, my reflexive response when anyone asks the question is always still the same: "What do you mean, 'Who's the best MC?' Don't be stupid. Everybody knows it's Rakim."

Listening to Rakim now, and listening to the styles of rapping that came before and after he arrived on the scene, before and after Paid In Full came out, I think I would argue, that while I think Biggie is technically a better rapper—more eloquent, more versatile, more skilled—Rakim remains the most important rapper of all time.

His flow-smooth, monotone, patient, cold-changed the way rappers sounded more than any other rapper before or since. And his vocabulary and his ability to put abstract intellectual concepts into rhyme expanded the rap palate in the same way. He was the first modern rapper. — Dave Bry

Chuck D: 1987-1991

Solo Albums: n/a
Group Albums: Yo! Bum Rush the Show (1987), It Takes a Nation of Millions to Hold Us Back (1988), Fear of a Black Planet (1990), Apocalypse 91...The Enemy Strikes Back (1991)
Biggest Hits: "Bring the Noise" (1988), "Don't Believe the Hype" (1988), "Fight the Power" (1989), "Welcome to the Terrordome" (1989), "911 Is a Joke" (1990)

All due respect to the Ramones, the Clash, the Sex Pistols, Andy Warhol, Honey Boo Boo Child, and anything else you think might be subversive, Public Enemy, in its prime, was the most punk rock thing in the history of mankind. In an era when mainstream America saw rap as a threat instead of a marketing opp, PE was the thing it feared most (even more than N.W.A.). Were Chuck D and company to emerge today, Fox News would go seriously fair and unhinged.

Chuck D was the face of it all. When he rapped about "the FBI tapping my telephones" it had an aura of menace and import that's wholly missing from hip-hop today. The "Fight the Power" video vs. the "New Slaves" rollout? Fear of a Black Planet vs. Nothing Was the Same? Please.

What's lost in the politics is the fact that Chuck D could rap his ass off and that his group was one of the tightest acts in showbiz history. Flow? Try the (regretably anti-semetic) first verse of "Welcome to the Terrordome." Hook? "You're Gonna Get Yours" from Yo! Bum Rush the Show. Storytelling? "Black Steel In the Hour of Chaos." Urgency? "Night of the Living Baseheads." On some level, rap is about being the all-consuming topic of conversation RIGHT NOW. Chuck had that crown longer than most. — Jack Erwin

KRS-One: 1987-1991

Solo Albums: n/a
Group Albums: Criminal Minded (1987), By All Means Necessary (1988), Ghetto Music: The Blueprint of Hip Hop (1989), Edutainment (1990)
Biggest Hits: "South Bronx" (1987), "The Bridge Is Over" (1987), "Criminal Minded" (1987), "My Philosophy" (1988), "Exhibit A" (1990)

The first five years of KRS-One's career were a study in contrasts. On one hand, he appeared on the cover of his first two albums holding guns (a bandolier and pistol on 1987's Criminal Minded, an uzi on 1988's By All Means Necessary); on the other, he founded the Stop the Violence movement, and released Edutainment, an album that signalled his (eventually sad and annoying) turn toward becoming the pedantic Teacha that hip-hop never really wanted.

Despite the hectoring, "Get off my lawn" b-boy stance he adopted later in his career, KRS-One had a nearly flawless run early in his career (shit, maybe he had a right to preach to us about the laws of hip-hop). Criminal Minded is a certified classic, both a benchmark for gangster rap and a touchstone for lyrical purists (see the "When I first heard Criminal Minded..." intro to De La Soul's Stakes Is High).

BDP's second album (recorded after the murder of Scott La Rock) featured the classic "My Philosophy". In his first half-decade in the game, Kris Parker offered the full gamut of what makes hip-hop beautiful (and, at times, awful): a hard world depicted in cold-eyed poetry; swagger on top of swagger on top of swagger; the sense that this art form could truly change people's lives (who better to talk about that than a former homeless MC). That KRS-One later became a caricature does nothing to diminish his initial run. Dude embodied hip-hop when he was young. Respect the teacher. — Jack Erwin

Ice Cube: 1988-1992

Solo Albums: AmeriKKKa's Most Wanted (1990), Kill At Will (1990), Death Certificate (1991), The Predator (1992)
Group Albums: Straight Outta Compton (1988)
Biggest Hits: "AmeriKKKa's Most Wanted" (1990), "True to the Game" (1992), "Wicked" (1992), "Check Yo Self" (1992), "It Was a Good Day" (1992)

It's very difficult these days, when you watch him blowing fake snow off his mustache in those Coors Light commercials, to concurrently keep in mind just how incredibly good Ice Cube was at rapping in his prime. He was the best there was. For the five year stretch that took rap from New York's first "golden era" to the moment when L.A.'s gangsta rap definitively repositioned the center of power out west, Cube was expanding the form's parameters in terms of lyrical scope, reportorial acuity, emotional ferocity, and political stridency.

This was also an era of American history defined by the acquittal of four policemen in the case of the videotaped beating of Rodney King and and the attendant riots that shook Los Angeles immediately afterward. Looking back, there is no important voice on the climate of the times than Ice Cube's.

His body of work from those years stands as proof: Writing "Fuck Police" and the majority of the best songs on N.W.A's 1988 classic Straight Outta Compton; the cross-country collaboration with Public Enemy's production team The Bomb Squad that resulted in his jaw-dropping solo debut Amerikka's Most Wanted; the Kill At Will EP, with the elegiac masterpiece "Dead Homies;" the explosive, rageful Death Certificate; and 1992's The Predator, which included both the crossover G-funk smash "Today Was a Good Day," and, in an interview interlude titled "Fuck 'Em," the very true, career-encapsulating statement, "Anything you wanted to know about the riots was in the records before the rights. All you had to do was go to the Ice Cube library and pick a record and it would have told you..."

No matter how many movies he makes, or funny-style Coors Light commercials, let no one forget: Ice Cube's best rap music was about as good as rap music's ever gotten. — Dave Bry

Q-Tip: 1989-1993

Solo Albums: n/a
Group Albums: People's Instinctive Travel's and the Paths of Rhythm (1990), The Low End Theory (1991), Midnight Marauders (1993)
Biggest Hits: "Bonita Applebum" (1990), "I Left My Wallet in El Segundo" (1990), "Can I Kick It?" (1991), "Check the Rhime" (1991), "Scenario" f/ Leaders of the New School (1992)

"Q-Tip is my title, I don't think that it's vital/For me to be your idol, but dig this recital." Those are the first lines delivered by Q-Tip on A Tribe Called Quest's 1990's People's Instinctive Travels and The Paths of Rhythm, a substantial name for a substantial debut. And even from the start, the 20-year-old Queens MC knew his lyrics would speak for him-and idolatry would follow regardless.

Part of the Native Tongues movement that included NYC's Jungle Brothers and Long Island's De La Soul (who released their debuts in 1988 and 1989 respectively), A Tribe Called Quest wasn't quite as serious as the former and not quite as quirky as the latter, focusing instead on real-life matters that were almost universally relatable. This was hip-hop in its fully mature stage just a decade in.

And while Tribe was a group, it was Q-Tip who carried them through that first album. In fact, even as Phife Dawg took a larger role as they delivered their first three classic LPs—People's Instinctive Travels, The Low End Theory, and Midnight Marauders—Phife would stick primarily to the volatile braggadocio while Tip provided the overwhelming steadiness that kept the group firmly grounded. On 1991's masterpiece The Low End Theory, Q-Tip kicked things off with a verse that explained his roots better than any biographer:

Back in the days when I was a teenager
Before I had status and before I had a pager
You could find the Abstract listening to hip hop
My pops used to say, it reminded him of bebop
I said, well daddy don't you know that things go in cycles
Way that Bobby Brown is just amping like Michael
Its all expected, things are for the looking
If you got the money, Quest is for the booking

From matters weighty ("Sucka Niggas") to not-so-weighty ("I Left My Wallet in El Segundo"), Tip managed to keep his wordplay nimble and his tone level, not unlike the Harmon mute era Miles Davis, as Phife gleefully filled the wilder John Coltrane role. When they recruited legendary jazz bassist Ron Carter to play on The Low End Theory's "Verses From the Abstract," Carter wanted assurances that there wouldn't be any profanity on the record. He needn't have worried—Tip didn't need them to make an impact. — Russ Bengtson

Scarface: 1990-1994

Solo Albums: Mr. Scarface Is Back (1991), The World Is Yours (1993), The Diary (1994)
Group Albums: The Geto Boys (1990), We Can't Be Stopped (1991), Till Death Do Us Part (1993)
Biggest Hits: "Mr. Scarface" (1991), "A Minute to Pray and a Second to Die" (1991), "Let Me Roll" (1993), "Hand of the Dead Body" (1994), "I Seen a Man Die" (1994)

Scarface is easily one of hip-hop's most important and underrated contributors. He's an uncompromising lyricist for whom storytelling, craft, emotion, and passion seem wrapped up in a single, inseparable, and powerful package in every single verse. He's one of the most consistent rappers in history—it's a challenge to find a verse that feels less than fully considered. His rap style is the definition of "timeless." Once he'd perfected that old-before-his-time flow, where each line seemed to rise and fall as naturally as breathing, it was like the invention of the wheel. We haven't replaced it because there still isn't anything that does what it does better.

He may not have had the chart success of some of his creative peers, but his legacy, his lasting influence, will certainly rival any of theirs. Forever. His five year run from 1990-1994 is one of the best in hip-hop history.

He started out a voice of fury and bombast, a percussive delivery in the vein of Ice Cube or Chuck D. For Scarface, political concerns were only a single dimension of a much wider spectrum of questions. His artfulness was tied up in wrestling with very real questions about the human condition, about the nature of truth, death, and the inner workings of the human mind. This last factor was a central concern of much of his music, and also the basis for what remains his most well-known song, the Geto Boys' "Mind Playin Tricks On Me." This track was a perfect midpoint between the cartoonish entertainment and existential drama that made his work schizophrenic in its contradictions.

He explored perception, morality, the contradictions and struggles of poverty, and coping with a life absent easy answers. But this high-minded praise isn't intended to hide the fact that he could be as morbidly entertaining as the best mindless gangster rap. His solo debut kicks off with "Mr. Scarface," and its opening chorus finds the rapper blasting away a fiend who tries to steal his crack rocks...to the tune of "The Itsy Bitsy Spider."

This was pulp fiction of the highest, most grotesque caliber, horror-comedy films set to banging production. It wasn't long before Scarface, as a solo artist, began approaching more serious subjects, his rap style downshifting into a spoken tempo (one hesitates to describe anything so anguished as "easygoing"). The impact could draw tears. "Now I Feel Ya" is a story about coming of age, but its implications are so much bigger than its simple narrative. It uses the biographical to paint a picture that understands nostalgia works best when it's bittersweet.

Throughout the early '90s, though, the razor-sharp edge to his provocations never disappeared, and often ran up against each other. On The Geto Boys' underrated 1993 album Till Death Do Us Part—the bulk of which was produced by frequent collaborator N.O. Joe—one moment was an extended meditation on processing death ("6 Feet Deep") and the next would be morbid humor like a murder story with names of breakfast foods intertwined into the narrative ("Cereal Killer").

By 1994's The Diary—now widely considered one of Scarface's true recording peaks—it was clear he'd fully established himself as one of the genre's most significant voices. The pulpiness of his earlier work had seeped into an unblinking realism. He was at times confrontational (as on the searing "Hand of the Dead Body") and reflective (the powerful meditation on death "Never Seen a Man Cry"). The humor hadn't entirely gone, either; "Goin Down," for example, interpolated German singer Nena's "99 Luftballons" into a sly come-on. — David Drake

2Pac: 1992-1996

Solo Albums: Strictly 4 My N.I.G.G.A.Z. (1993), Me Against the World (1995), All Eyez On Me (1996), The don Killuminati: The 7 Day Theory (1996)
Group Albums: Thug Life: Volume 1 (1994)
Biggest Hits: "I Get Around" f/ Shock G & Money-B (1993), "Keep Ya Head Up" (1993), "Dear Mama" (1995), "California Love" f/ Dr. Dre (1995), "How Do U Want It" f/ K-Ci & JoJo (1995)

First things first: 2Pac was a disruptor, perhaps hip-hop's most significant in its three-decade history. And any rapper in contention for the Greatest of All Time—as he obviously is—is going to end up with a pretty unquestionable shot at one of hip-hop's great five year runs.

Interestingly, while Pac is one of the few rappers whose career not only included several classic albums, but also had an enormous, unprecedented impact, his is also one of the more inconsistent half-decades of dominance. He was an incredibly consistent rapper, particularly at his peak. But his early work has become so dwarfed by the artistic accomplishments of his final three albums that, while he's unquestionably one of hip-hop's foundational entities, it's difficult to suggest that his 5-year-run is the equal of his overarching importance.

That said: his early work, while spotty and not nearly as transcendent as his '95-'96 output, was still unquestionably classic and influential, and only suffers from the comparison to later heights he would achieve. From his guest spots on albums by Spice 1 and MC Breed to Strictly 4 My N.I.G.G.A.Z. classics (and Hot 100 hits) like "Keep Ya Head Up" and "I Get Around," it was clear even early on that there was a new voice that was fusing the populist underclass theatrics of N.W.A. with the righteous polemics of Public Enemy into a new, revolutionary model. While his rap style has been disparaged for years by those who undervalued more abstract x-factors like charisma, star power, pathos, and songcraft over the more technical aspects of an MC's toolkit, Pac had managed to more directly and effectively wed aesthetics with ideology than perhaps any rapper before or since.

His five-year run was broken up by a jail stint, court dates, a shooting, and multiple movies. And yet he still makes it onto this list with ease, because what he accomplished—a class-conscious, accessible, radical, and oppositional personality that bled from his real life into his music—is so completely singular, so entirely unprecedented in the genre. His ability to so thoroughly blend art and politics, theater with reality, and the popular with the cutting-edge spun out endless complications within the genre.

Although many pieces written about Pac act as if the story has ended, the echoes and ramifications of his short and sudden impact in the industry continue to coil outward. He had an ability to put his fingers right along the faultlines that undergirded so many of the conflicts and challenges faced not just by the artform, but by America broadly.

Many think we've learned all we can from Pac's life and death, but we are still feeling the reverberations from his all-too-short time on the planet. The vexing social problems he pushed to the forefront in his music, by and large, still remain. What has changed is the popularization of rhetorical tactics that rappers continue to use today, to speak truth to power in a way that cuts through the noise. Give a man a fish, and you feed him for a day. Pac was more of a teacher. — David Drake

Redman: 1992-1996

Solo Albums: Whut? Thee Album (1992), Dare Iz a Darkside (1994), Muddy Waters (1996)
Group Albums: n/a
Biggest Hits: "Blow Your Mind" (1992), "Time 4 Sum Aksion" (1993), "How High" (1995), "Can't Wait" (1995), "Whateva Man" f/ Erick Sermon (1996)

Rap fans of today may not know how absolutely top-level Reggie "Redman" Noble once was as a lyricist. That's because he faded into the obscurity of tossing out somewhat subpar music videos and freestyles. His last album, Reggie, came out nearly three years ago and was a flop in every way possible. At this point, he might be better known for his legendary MTV Cribs episode, which resurfaced earlier this summer and subsequently went viral, than for earlier material.

However, there is a reason Eminem listed Redman on his list of best rappers.

While two of Redman's most commercially successful albums came out in 1998 and 1999 (Doc's Da Name 2000 and Blackout! with Method Man), his run from 1992 to 1996 was his creative peak. It all started with Erick Sermon and EPMD. Bringing him into their Hit Squad fold, the duo gave him his first opportunities to prove himself on record. On 1992's Strictly Business, EPMD featured Redman on the closing verse of "Head Banger." The song was later released as the album's second single, and Redman stole the show with his rapidfire flow. After hearing "Head Banger," then-Def Jam executive Lyor Cohen is believed to have said, "We made the right choice" in signing Redman to the label.

On September 22, 1992, Redman released his debut album, Whut? Thee Album. The Newark native, who was a DJ before he became a rapper, had his hands on almost all of the album's beats, receiving some assistance from Erick Sermon along the way. Redman spent most of 1991 and 1992 crafting the album, and the result was an album that blended old-school funk with Redman's razor sharp flow, wild storytelling, and colorful punchlines. Whut? Thee Album spawned three singles: "Blow Your Mind," the hard-hitting "Time 4 Sum Aksion," and "Tonight's Da Night." It also had cult classics like "How To Roll A Blunt."

In 1994, Redman released Dare Iz A Darkside. As the album's intro, "Dr. Trevis," indicated, this was a departure from his debut effort. His staccato flow was just as sharp as it had been on Whut? Thee Album, and the funk influence could still be heard in the multiple samples of The Parliament. But Dare Iz A Darkside's production was more minimalistic and edgier than its predecessor, and Redman's personality got even wilder. Two singles came out for this album: "Rockafella" and "Can't Wait."

Two years later, Redman returned with his third solo album, Muddy Waters. The album is considered Redman's finest body of work, so much so that Redman has been talking about working on a sequel even before he released Reggie. Muddy Waters is the perfect blend of funk, hardcore grittiness, and more laidback offerings like "On Fire." This was the album where Reggie Noble cemented himself as one of the finest rappers of this era. It would go on to have three singles: "It's Like That (My Big Brother)," "Whatever Man" with Erick Sermon, and "Pick It Up."

In between these years, there was a diverse range of guest appearances. How diverse? In 1993, he started off Jodeci's "You Got It," an album cut off Diary Of A Mad Band. The following year, he jumped on a song called "My Style, My Steelo" with Shaq. Redman takes the second verse, and it is apparent in Shaq's closing verse that the basketball superstar is trying to emulate the swing and fluidity of his guest's delivery. In 1996, he appeared alongside Method Man and The Dogg Pound on 2Pac's "Got My Mind Made Up," a song off All Eyez On Me.

And none of that included the release of Redman's biggest song, "How High," which came out in 1995. The collaboration with Method Man, which was originally just intended for The Show soundtrack, peaked at number 13 on the Billboard Hot 100 charts (despite Redman saying "Fuck the Billboards" in the song) and triggered the pairing of Redman and Method Man as a duo. Red and Meth's first single together set the stage for the wildly successful Blackout! album and How High movie. On it's own, "How High" is the best stoner anthem ever.

Altogether, that's two classic albums, one very good album, several show-stealing guest appearances, and a stoner anthem that inspired a cult classic film. Not bad for five years' work. — Dharmic X

Bun B: 1992-1996

Solo Albums: n/a
Group Albums: The Southern Way (1992), Banned (1992), Too Hard to Swallow (1992), Super Tight (1994), Ridin' Dirty (1996)
Biggest Hits: "Something Good" (1992), "Front, Back & Side to Side" (1994), "One Day" (1996), "Murder" (1996), "Diamonds of Wood" (1996)

Between 30 and 40 songs as a member of UGK between the years 1992-1996, Bun released some of the best music of the period, the basis for a reputation he's since earned as one of hip-hop's elder statesmen. It's also tough to remember how different his reputation was at the time; his highest profile appearance in that period was likely on the soundtrack to Menace II Society, which included the group's unrepentant drug dealer anthem "Pocket Full of Stones (Port Arthur Remix)." The song told the rise and fall of local drug dealers from a first person perspective with a forceful, hard-headed, confrontational attitude handed down from N.W.A.

Of course, it's impossible to talk about Bun B without mentioning his counterpart, the balance and musical mastermind behind UGK, Pimp C. Pimp was the group's Id, the unvarnished truth-teller whose rap style was all about directness. From a rapping perspective, he was Eazy E: high-pitched and nasal, his verses were unadorned with lyrical flourishes. (He was also largely responsible for crafting the group's unique sound, a country funk style that had a more organic sound than the synthesizers popular on the West Coast at the time.) In contrast, Bun was a rapper's rapper. When the duo linked up in the late 1980s, they were no doubt seen by onlookers as little more than another regional gangster rap group, albeit one with a distinct sound. But it would soon become clear that Bun's distinct baritone was much more than a booming clearing house for gangster rap cliches.

One of the things that stood out about the duo from the beginning was Bun's rap style. Rigid and blocky, his delivery had a barreling muscularity, which contrasted directly with his precise, intricate writing style. His turns of phrase had a sticky, unforgettable quality, with memorable imagery put together with an effortless writerly panache: "Livin' real smooth like aloe vera lotion," goes "Pocket Full of Stones (Port Arthur Remix)," "I'm sellin' crack rock, the devil's love potion." Or on 1996's "Break Em Off Somethin'" with Master P, which adds the pugnacious confrontationalism: "My nigga, that's how these G's be/We three, me, C, and Master P/Sippin' on Gin and Kiwi, fuck popping in your CD/We popping them clips."

Pimp and Bun both played the bad guy, embodying gangster rap's core contradictions. Violence and snarled threats were the lingua franca. They reached a creative apex during this five-year run on 1996's Ridin' Dirty, when Bun's infamous verse on "Murder" packed bars together so tightly they seemed to interlock and unfold with morbid grace. You could smell the red jelly leaking from the belly of the Pelle Pelle-clad target of Bun's wrath, and in that moment, it was clear that this was more than just your typical gangster rap, but was the most artful possible way to make an impact felt. — David Drake

The Notorious B.I.G: 1993-1997

Solo Albums: Ready to Die (1994), Life After Death (1997)
Group Albums: Conspiracy (1995)
Biggest Hits: "Juicy" (1994), "Big Poppa" (1994), "One More Chance / Stay With Me (Remix)" (1995), "Hyponotize" (1997), "Mo Money Mo Problems" (1997)

We all know precisely when and where Biggie's five-year run ends: Early morning hours of March 9, 1997, outside a VIBE magazine party at L.A.'s Petersen Automotive Museum. When Christopher George Latore Wallace died at age 25 from multiple gunshot wounds in a case that will remain officially unsolved forever, Voletta Wallace lost her son, Faith Evans lost her husband, Tyanna and CJ lost their dad, and the world lost a motherfucking rap phenomenon.

The Notorious B.I.G.'s entire career was flawless, moving from strength to strength like trees to branches, cliffs to avalanches. His was a case of extraordinary raw talent nurtured in the bosom of BK's crack-infested streets and peppered with periodic visits to a Jamaican sound-system playing uncle and a New Orleans jazz legend neighbor who played the roles of musical mentor, recording engineer, and cinematographer. Biggie Smalls was a perfect storm.

So where do we start? Limiting ourselves to just five years, we lose surprisingly little. His crucial 1991 demo tape, which was recorded in DJ 50 Grand's basement, re-recorded at Mister Cee's home studio, submitted to Matty C at The Source, and which eventually landed in the hands of an Uptown Records A&R named Sean Combs who was busy building an empire of his own. Biggie made a handful of records in 1992, including an unreleased song for Uptown called "Biggie Got The Hype Shit," a Heavy D posse cut called "A Buncha Niggas" on which Biggie shares the mic with 3rd Eye, Guru, Rob-O, and Busta Rhymes, a collab with Neneh Cherry called "Buddy X," and another collab with Aaron Hall called "Why You Tryin' To Play Me."

Believe it or not, every other Biggie record you know and love falls into his miraculous five-year run. The Who's The Man? soundtrack album dropped on April 20, 1993 and Biggie's infectiously reckless "Party and Bullshit" was released as the fourth single in late June. Tupac Shakur reportedly kept the cassingle on repeat, and made periodic visits to Bed-Stuy BK to kick it with the 21 year-old MC who described himself as "a chubby nigga on the scene."

A couple months later came Mary J. Blige's sublime "Real Love (Remix)," with Biggie's exuberant opening line "Look up in the sky, it's a bird, it's a plane!" After that came the remix of Super Cat's "Dolly My Baby." Biggie ended that verse with a Papa San hook because he knew what it meant to rhyme alongside the Don Dada, so why not represent his own yardie roots? On the title cut from Mary J. Blige's What's the 411? Remix album, Biggie let loose a scandalously slack interlude that would eventually evolve into "Dreams" (of fuckin' an R&B bitch), a song so raw that it prompted Patti Labelle to call Biggie up and demand an apology—which he promptly gave her.

Despite what you may have heard, Voletta's son had nuff broughtupsy. He closed out 1993 with the legendary "Garden freestyle" recorded at the Budweiser Superfest ("I got seven Mac 11s, about eight 38s, nine 9s, ten Mac 10s, the shits never end...") during which Big demonstrated that his real firepower was the booming cannon he kept concealed in his larynx-the one he used to blow 2Pac, Scoob, and Shyheim off the MSG stage.

By 1994 we were hearing the first singles off Ready To Die, "Juicy" b/w "Unbelievable"—perhaps the best-loved and best-ever Biggie songs, respectively—followed by "Big Poppa" b/w "Warning." The crucial guest appearances began that same year with "Flava In Ya Ear," which effectively ended Craig Mack's career and made Bad Boy Records a one-man show (aside from Puffy of course).

By 1995 it was all about the "One More Chance/Stay With Me" remix, which made Biggie a commercial force across the country, ceritified platinum just as his beef with Pac was getting truly scary. And then everyone became obsessed with "Who Shot Ya" and the Jr. Mafia joints—"Get Money" and "Players' Anthem"—not to mention the whole Lil Kim album Hard Core (Biggie's background vocals on "Drugs" may be his most slept-on performance).

Before even cracking the cellophane on his certified-diamond sophomore double-album, we must address some royal guest spots, including "Brooklyn's Finest" with future King of NY Jay Z, "This Time Around" with lifetime King of Pop Michael Jackson (aka "My nigga Mike"), and "Can't Stop The Reign" with King of the Paint Shaquille O'Neal. And let's not forget the remix to 112's "Only You" featuring Biggie and Ma$e, a definitive Bad Boy party-starter that ranks right up there with posthumous Puffy release "Benjamins."

The whole macabre Life After Death experience kicks off with "Hypnotize," a club banger that became the soundtrack for Biggie's chaotic/cathartic funeral procession through BK. Other indelible highlights include the double-time tour-de-force "Notorious Thugs," the redemptive "Sky's The Limit," and the unrepentantly salacious "Fuckin You Tonight" featuring R.Kelly. But really you can pick any one of the 24 tracks on this masterpiece and wax poetic ad naseum. Both the album's Primo cuts—"Kick In The Door" and "10 Crack Commandments"—are all-time classics, despite the fact that Puffy said "this joint ain't hot" of the former and Chuck D sued over the latter. You could spend a lifetime puzzling over ominous subliminal-studded records like "What's Beef," "Long Kiss Goodnight" and "You're Nobody Till Somebody Kills You."

The greatest five-year run in hip-hop history comes to an end with Biggie's final recording, laid down the night before he was murdered: an unbearably epic song that would be titled "Victory" and released on Puffy's No Way Out album. "You heard of us," Biggie intones, "the murderous, most shady." Near the end of his verse he calls himself "the underboss of this holocaust," leaving Busta screaming "where the fuck you at?" What Puff said on "Benjamins" was true: "It's all real in the field." Sometimes too real. — Rob Kenner

Andre 3000: 1994-1998

Solo Albums: n/a
Group Albums: Southernplayalisticadillacmuzik (1994), ATLiens (1998), Aquemini (1998)
Biggest Hits: "Player's Ball" (1994), "Elevators (Me & You)" (1996), "Jazzy Belle" (1996), "ATLiens" (1996), "Rosa Parks" (1998),

The André 3000 you remember may have a Silky Johnson perm and suspenders, but before the perm, before the Grammy's, and before the money Dré was just a teenager with a fade in a Braves jersey who wanted to be heard. Big Boi, the other half of OutKast, wasn't born with a fur coat and a glass of Crown Royal, he earned that. There was a time before the duo were two dope boys in a Cadillac. They were, at one-point, just two dope boys rapping in the Tri-Cites High School Cafeteria.

A 19-year old André kicked off one of the best five-year runs in rap history with the release of the duo's first single, "Player's Ball." The Organized Noize produced track marked OutKast's introduction to the world, and the public braced for the duo's debut album, Southernplayalisticadillacmuzik.

The debut album was just the beginning, not only for OutKast, but also for Atlanta as a whole. The debut album kicked down the door for the rest of the Dungeon Family, and Atlanta as a whole. As André said amidst boos at the 1995 Source awards, "The South got something to say." The south did have something to say and thanks to releases by Outkast and fellow Dungeon Family group Goodie Mob the south was beginning to be heard. Southerplayalisticadillacmuzik put Outkast on the map. They were being heard, they were being watched and they acted accordingly following their debut with the classic ATliens. The album further defined OutKast's sound; their Atlanta slang and southern twang made it cool to be from below the Mason-Dixon line in the rap industry.

André has always been eccentric and creative, these characteristics were in full effect on Outkasts third release, Aquemini. Outkast received their first Grammy Nomination for Aquemini. The commercial and critical success was made possible by the groundwork laid down on their first two offerings. Each album pushed the boundaries further and broadened the definition of rap.

Big Boi and André's genre-bending music redefined the genre as a whole. The 5-year span was not just one of growth for Dré and 'Twan, but also for rap as a whole. Southernplayalisticadillacmuzik, Atliens, and Aquemini changed the meaning of what it was to be a rapper, using elements of gospel, funk, blues, and jazz to create something new. We owe our liberal definition of rap today to the rule breaking and pioneering outcasts; André and Big Boi. The permed André of the "Hey Ya!" video is not possible without the cornrowed André of the "Player's Ball" video, the same way that Speakerboxx/The Love Below is not possible without Southernplayalisticadillacmuzik. Thankfully we have one of the greatest 5 year runs to look back on and remember what made Speakerboxx/The Love Below, the best selling rap album of all time, possible. — Austin Weatherly

Ghostface Killah: 1996-2000

Solo Albums: Ironman (1996), Supreme Clientele (2000)
Group Albums: Wu-Tang Forever (1997), The W (2000)
Biggest Hits: "All That I Got is You" f/ Mary J. Blige (1996), "Daytona 500" f/ Raekwon & Cappadonna (1996), "Motherless Child" (1997), "Apollo Kids" f/ Raekwon (1999), "Cherchez La Ghost" f/ U-God (2000)

Ghostface Killah's career is fascinating because of the way he improved as a rapper and subsequently rose to prominence amongst his many prominent colleagues in the Staten Island based nonet, Wu-Tang Clan. When the Clan first came upon the scene, Ghostface, for reasons that seemed like they might have to do with a nefarious past, never showed his face. (Hence his name.) The shadowy look seemed to suit him, because on the group's first album, 1993's Enter the Wu-Tang (36 Chambers), he pretty well stayed in the shadows, giving his brethren Method Man and Ol' Dirty Bastard the spotlight. His rapping was fine, passionately voiced, but not outstanding, rhymes-wise.

But a funny thing happened on the way to the second Wu-Tang Clan album. As the more prominent members released a string of solo albums that were all produced entirely by Wu founder the RZA, and so heavy with guest appearances from fellow clansmen that they can all pretty fairly be described as Wu-Tang group albums, Ghostface started to sound like one of the more dynamic and distinctive lyricists that anyone had ever heard.

The big wake-up moment was Raekwon's solo debut, Only Built for Cuban Linx.... Ghostface was all over it; so much that his name appeared on the cover with Raekwon's-the two had found such a cohesive style, they were sort of operating as a duo, an internal Wu-Tang side project. When rap fans came to realize what they had on their hands—namely, the single best rap album ever ever recorded in the history of the universe—Ghost's stock rose accordingly.

His own solo album followed in suit. Another stone-cold classic, filled with rhymes as vivid and colorful as the rainbow of home-dyed Wallabee Clarks all over the cover, Ironman established Ghostface as a master of a new kind of style: stream-of-consciousness word salad, dressed with Jabberwockian slang and a willingness to display emotion that had been all too rare in the macho world of rap up to that point. "All That I Got Is You," the album-closing duet with Mary J. Blige, joined Tupac's "Dear Mama" in setting a standard for modern Mother's-Day anthems as well as descriptions of life in poverty. If you can listen to it without welling up at the part where Ghost describes his mom wiping the sleep out of his eyes with her fingertip, well, you're a stronger man than I.

By the time the second official group album, Wu-Tang Forever, came around in 1997, Ghost was ready to shine brighter than ever. He fairly dominates the sprawling, double-length opus (along with RZA's scintillating soundscapes), delivering what many people (this one person sitting here typing this among them) believe is the single greatest rap verse of all time, on the song "Impossible."

Wu-Tang Forever, though, turned out to be peak-Wu-Tang. Over the next two years, as Bad Boy's shiny suits ushered the "bling era" into hip-hop, the groups' grimy aesthetic fell out of favor. Second solo albums from Method Man and Raekwon fell flat. Other producers started showing up in album credits, RZA having seemingly used up all his juice. The guys separated, appearing together, or even getting in the same room, increasingly rarely. Folks moved to other parts of the country. The magic was gone.

But leave it to Ghostface to deliver an amazing parting shot on behalf of his crew. One more relentlessly intense display of rap skill to put a seal on the Twentieth Century and open the next one with bold, brave-new-world panache. Supreme Clientele had a quiet run-up to release, and a low-key smaller-scale launch. The song titles are listed in the wrong order on the album packaging. The musical tracks are dusty, based on samples of old soul records, more reminiscent of 36 Chambers, in many ways, than any Wu-Tang project since. And, Jesus, the rhymes! Ghost had perfected his style-a whirlwind sirocco of descriptives and memories expressed with breathless emotionality and his patented "vivid laser-eye guy" attention to detail. It didn't sell as well as its predecessor, no Wu albums were putting up strong numbers at that point. But for the heads in the know, connoisseurs of the finest rap lyrics available, it was clear that Ghost had established himself as the most important Wu-Tang rapper of them all. The one that would carry the flag forward. — Dave Bry

Jay Z: 1997-2001

Solo Albums: In My Lifetime, Vol. 1 (1997), Vol.2...Hard Knock Life (1998), Vol.3...Life and Times of S. Carter (1999), The Dynasty: Roc La Familia (2000), The Blueprint (2001)
Group Albums: n/a
Biggest Hits: "Hard Knock Life" (1998), "Big Pimping" f/ UGK (1999), "I Just Wanna Love U" (2000), "Izzo (H.O.V.A.)" (2001), "Girls, Girls, Girls" (2001)

Jay Z's great run was, like 2Pac's, a six-year one. But it's even worse to cut off a year for Jay, as the bookends of that six year run—1996's Reasonable Doubt and 2001's The Blueprint—have, over time, come to be considered the crown jewels of the Jay Z catalog. The former's reputation was burgeoned, at least initially, by a nostalgia for the era it captured: DJ Premier beats, heavily coded drug game-influenced rap writing, intricate, conceptually ambitious song construction. Compared to the club-friendly, trend-chasing, pop chart-dominating music of late-'90s Jay, Reasonable Doubt was respectable. Everything about it, from the Real Heads-approved Premo beats to the black-and-white cover art, was dignified.

It also wasn't very successful, at least initially. "Classic," Jay would argue later. "Shoulda went triple." But it didn't. And while it was definitely underrated at the time, and remains one of his best records, it also doesn't capture the heights Jay would attain over the next five years, as his persona took full flight. Jay was always, above all, a success-at-all-costs achiever. His period as chronicler of the drug dealer's day-to-day was a stepping stone—not the end zone. He was to embody ambition, success by any means. And his articulation of this—from 1997 until 2001, when The Blueprint represented a new, reflective moment, in addition to accidentally creating a production sea change in hip-hop to the soulful-was one of hip-hop's true great five-year runs.

Vol. 1, of course, is widely considered an overreaching mis-step in his attempt to not only cross over, but to become New York's king in the wake of Biggie's murder. But beyond the surface, it's got some of his best songs, from stunting pinnacles like "Imaginary Player" to perhaps his best street track ever, "Where I'm From." Vol. 2 made up for its predecessors deficiencies by turning everything inside out. Where the former record was all strong album tracks and medium singles, Hard Knock Life was all about immediacy. A string of hits helped, but the title track in particular took Jay to another level of fame, making him the true superstar of hip-hop's commercial crossover moment.

"Hard Knock Life" redefined Jay's career, more than the entirety of Reasonable Doubt. It gained such potent traction in the story of his success that a decade later, a still-pre-"Lollipop" Lil Wayne would talk about how he was seeking a "Hard Knock Life"-type record of his own. There was a shotgun approach to Jay Z's methodology on Vol. 2, incorporating all the latest producers and guests. Where Reasonable Doubt failed to measure up to similar inspirations like Only Built 4 Cuban Linx, Vol. 2 had no real competition in its effort to epitomize its time. Bridging the new roughneck aggression of emergent star DMX with the rising Southern bounce sounds approximated by Irv Gotti on "Can I Get A..." and reinvented by Timbaland, Jay's unrufflable nonchalance was comfortable over a wide variety of styles. As apocalyptic triton spasms of "Money, Cash, Hoes" ripped through the very fabric of the track, Jay was a cooly unaffected superhero.

Vol. 3 wasn't the blockbuster success Hard Knock Life had been. But it did show an increasingly ambitious rapper expanding on the sound he'd become most closely identified with. He was beginning to sell a lifestyle. The smash single "Big Pimpin" was also emblematic of the success that hip-hop was experiencing more broadly. It was a "corporate" rap era—one of unprecedented diversity, experimentalism, and popularity.

But what capped his five-year run was pioneered on the underrated Dynasty and fully fleshed out in The Blueprint. Rather than the formalist exercise of Reasonable Doubt or the mercenary hit-chasing of his late-'90s popular peak, Jay helped set a new sonic template. In contrast to the techno-futurist video arcade that hip-hop had become, Kanye, Just Blaze, and Bink! utilized soul samples to give Jay Z's sixth full-length a new style. Organic instrumentation and soul samples were in. But it no longer sounded like the boom-bap era; instead, it was as informed by the immediate pop appeal of Puffy's Hitmen, cleaning up the samples so they sounded as clear as one of Mannie Fresh's synthesized basslines. Thematically, too, Jay seemed—for the first time since his debut—to stretch out and consider what it took for him to reach what surely must have felt like his pinnacle.

Jay's 5-year run included four No. 1 albums (In My Lifetime...Vol. 1 hit No. 3) and 19 songs in the Hot 100. He dodged a significant legal hurdle in the stabbing of Lance "Un" Rivera, went from a respected underground New York MC to a credible King of NY candidate, from an underrated street rapper to one of the genre's biggest commercial stars to one of its most acclaimed. — David Drake

Eminem: 1999-2003

Solo Albums: The Slim Shady LP (1999), The Marshall Mathers LP (2000), The Eminem Show (2002)
Group Albums: Devil's Night (2001)
Biggest Hits: "My Name Is" (1999), "The Real Slim Shady" (2000), "Cleanin' Out My Closet" (2002), "'Till I Collapse" f/ Nate Dogg (2002), "Without Me" (2002), "Lose Yourself" (2002)

It wasn't until Eminem's second proper album that he'd note: "Y'all act like you've never seen a rapper before." He was talking to everyone listening, which at the time, felt like it was, in fact, everyone. This was in May 2000, on the lead single from The Marshall Mathers LP, "The Real Slim Shady," five months into the new millennium, one year and three months after the release of The Slim Shady LP. In the last year, Eminem had seemingly done what then felt impossible: Emerged as the first solo white rapper respected and revered by the rap community in the modern era of rap. This was around the same time Everlast and Kid Rock and Fred Durst were kicking around their not-quite-rap careers. This guy from Detroit, who rapped about doing every drug in every book, whose pop culture base of reference was stunningly topical and of-the-moment, this guy who Dr. Dre-Dr. Dre!-had endorsed and signed off on and rapped on his record! Nobody expected Eminem, and when he happened, it felt like a sonic blast across the entirety of the music spectrum, a time to recallibrate all the old methods of calibration. Eminem was a rapper who went to dark places, and to comic places, who had an anarchic persona that just didn't exist in rap at that moment: Nobody didn't give a fuck like Eminem didn't give a fuck. And moreover, this guy could rhyme like nobody we'd heard before either, words sticking to and exploding off of one another in staccato, in cadence, in ways our ears had to readjust to. To say he was compellingwould be a vast understatement. It really was like we'd never seen a rapper before.

But by the time The Marshall Mathers LP rolled around, he'd proven himself so much more than a rapper-something resembling more cultural figurehead than anything else. "Stan," with its Dido-infused chorus and story-rap about an obsessive fan. "Kim," the peak-psychosis of Eminem played out in one of the most stunning, disturbing rap tracks ever recorded. "The Way I Am," with its relentless, machine-gun fire flow. Where The Slim Shady LP got pretty solid (if not great) reviews, The Marshall Mathers LP got universally stellar reviews. Eminem simply took the ideas from his last album, and expanded upon them, grew them in ways we didn't think they could be grown, the difference between good sound and high fidelity. Between the two albums, Em more than proved his mettle rapping on Dr. Dre's big comeback record, 2000, in spots that blew away anybody else on them ("Forgot About Dre," for example), or even post-humous B.I.G. record Born Again (on "Dead Wrong"). The next move was only natural: 8 Mile, a feature-length film loosely based on the autobiographical details of Eminem's life. Of course the film would yield one of Eminem's most popular and crucial songs in "Lose Yourself," which would then go on to win an Academy Award. — Foster Kamer

Cam'ron: 2001-2005

Solo Albums: Come Home With me (2002), Purple Haze (2004)
Group Albums: Diplomatic Immunity (2003), Diplomatic Immunity 2 (2004)
Biggest Hits: "Hey Ma" f/ Juelz Santana, Freekey Zeekey & Toya (2002), "Oh Boy" f/ Juelz Santana (2002), "On Fire Tonight" f/ Freekey Zeekey (2002), "More Gangsta Music" f/ Juelz Santana (2004), "Down And Out" f/ Kanye West & Syleena Johnson (2004)

If Cam'ron had done nothing between 2001 and 2005 but drive his famous pink Range Rover ("Range look like Laffy Taffy") around, that would, by itself, be one of the greatest runs in rap ever. "No matter who's driving, if they are in that car, you're a star," he told MTV News in 2004. "If your grandmother got in that driver's seat, she's gonna be signing autographs. It just attracts attention." But Cam didn't just spend the early 2000s making pink cool-although he did do that, to the extent that he was the subject of a New York Times Style section pieceon the color. He was also busy taking over New York by pushing the city's rap style to its logical extreme, his ear for incredible soul samples surpassed only by his ability to write absurdly dense rhymes that tumbled out like hood tongue twisters.

Signing with Roc-A-Fella in 2001, Cam became a key part of the label's dominant early-decade run, putting out two indisputable solo classics, Come Home With Me and Purple Haze and creating some great collaborations, with Jay Z and Kanye West. During this period, The Diplomats were one of the most exciting things in rap, powered by hot, all-hands-on-deck songs like "Hey Ma" and "Dipset Anthem," the blockbuster (in intentions, if not sales) Diplomatic Immunity and a steady stream of mixtapes. Cam was so good he managed to make people excited about stray Hell Rell verses. New York hasn't had a movement as dominant and all-encompassing since. Purple Haze, which remains Cam's best album, led to much of the industry bitterness that would help drive him out of the spotlight, but it's just as possible it was Cam'ron's peak because it perfected his formula to a degree that needed no further improvement.

If he never quite crossed over in the same way as his contemporary as the face of New York, 50 Cent, it was because Cam'ron is above all a rap nerd's rapper, an artist whose instincts for making great songs are surpassed by his interest in stringing together lines of words that sound amazing when combined. The trademark Cam'ron line (say, "Parked in the towaway zone/Chrome/Don't care, that car throwaway, homes...") leans on internal rhymes, strings out one rhyme for longer than expected and piles up layers of absurdity. His work is extremely inviting to the kind of people who geek out over lyrics, almost every line of it immensely quotable. Even though the contents of his lyrics, particularly the moments of intense misogyny and violence against women, prompted plenty of serious critiques, Cam is also one of rap's most delightfully varied voices, one minute a stone cold killer threatening to kill his enemies and "let the fish eat [their] flesh," the next an absurdity-minded business man, comparing himself to the plant from the musical "Little Shop of Horrors." And he was never funnier, more self-aware or more impossibly clever than during these years.

If you're still not convinced, it was also during this run that Cam made his legendary "O'Reilly Show" appearance (in 2003, with Dame Dash), spawning rap's favorite meme and the only rebuttal needed to any Cam'ron hate in any era: "you maaaad." — Kyle Kramer

50 Cent: 2002-2006

Solo Albums: Get Rich or Die Tryin' (2003), The Massacre (2005)
Group Albums: Beg For Mercy (2003)
Biggest Hits: "In da Club" (2003), "P.I.M.P." (2003), "21 Questions" f/ Nate Dogg (2003), "Candy Shop" f/ Olivia (2005), "Disco Inferno" (2005)

When the Dr. Dre and Eminem-endorsed 50 Cent exploded onto the pop culture radar in 2003 with "In Da Club" as the lead single off of Get Rich or Die Tryin, Queens knew what was coming. Anybody who had heard the way 50 took on nearly every popular rapper with "How to Rob" knew what was coming. Anybody who had heard anything 50 did in 2002, from mixtapes and quasi-official releases (50 Cent is the Future, or Guess Who's Back, or God's Plan, or No Mercy, No Fear) to the plinking beat of "Wanksta" knew what was coming. But even they couldn't possibly understand the way the rest of the world-to whom, this rapper with the off-putting charm and the sing-song cadence and the come-from-behind backstory about being shot multiple times, in the face-didn't know what to expect. Which might account for why, by the end of 2003, 50 was everywhere. 50 was on TRL giggling about having destroyed Ja Rule's career. 50 was in every bar, every car, and every club from the cities to the suburbs and back. 50 was on the mixtape to your girl with "21 Questions." He was on your running mix with "What Up Gangster." He was back on TRL with "P.I.M.P." or "Patiently Waiting," on the radio with "Many Men" and "If I Can't." The effect that Get Rich or Die Tryin' had on the cultural landscape was palpable, if only for the fact that it was just everywhere. 50 never relented from riding on the success of Get Rich or Die Tryin', building his G-Unit label into rap's dominant juggernaut, and resurfacing solo with 2005's The Massacre, an unashamed rehash of its predecesor's genius. And one that sold a million copies in its first week in stores. — Foster Kamer

T.I.: 2003-2007

Solo Albums: Trap Muzik (2003), Urban Legend (2004), King (2006), T.I. vs. T.I.P. (2007)
Group Albums: n/a
Biggest Hits: "Rubber Band Man" (2003), "Bring Em Out" (2004), "U Don't Know Me" (2005), "What You Know" (2006), "Whatever You Like" (2007)

T.I.'s commercial peak came just after his best five-year period on a creative level; one can't help but think he might have received more serious consideration as one of hip-hop's best MCs had his twin 2008 No. 1 singles ("Whatever You Like" and "Live Your Life") coincided with his 2003-2007 run. For it was that period in the mid-2000s that T.I. often seemed like hip-hop's most important new voice. He represented Atlanta at a time when it was truly on the ascent, introducing a new sound, new culture, and new plethora of street heroes to the charts. Of them all, Tip seemed to have best captured a nobility of purpose, a moral sense, and a down-to-earth humanity that set him apart from then-triumphant stars with a more bulletproof persona—Jay Z, 50 Cent, Cam'ron, and Young Jeezy. He was from the trap, but he was human, and he sold stories about his origins in a way that often seemed to undercut any sense of glorification.

From a creative perspective, Tip confounded outsider's presumptions about Southern rap. Although delivered in a strong Southern drawl, he was a fierce lyricist with a fluent double-time, he could keep up with the best New York lyrical miracles. He also had a rough street edge that gave his early singles a threatening dimension. And yet he retained the more blues-inspired first-person confessional narratives popular in the wake of rappers like 2Pac and Scarface.

His career almost never happened; his debut record had flopped, despite high-profile beats from The Neptunes, and he was forced back underground. His reign began in earnest in the summer of 2003, with Volumes 2 and 3 of his In Da Streets mixtape series. Then there was his scene-stealing verse on Bonecrusher's "Never Scared," one of those verses that launches a career. The rapper slowed his flow to make each word deliberate, letting the grit fleck his vocals as he dissed a host of unnamed rivals. Trap Muzik—a true hip-hop classic—came next, laying out a multi-dimensional artist unafraid of conflict, but far from unconflicted. He claimed the throne as King of the South, dispatched Lil Flip in one of the most one-sided victories in hip-hop history.

From there, T.I. was on the ascent. His third album, 2004's Urban Legend, landed the rapper his first top ten single with the Jay Z-sampling "Bring 'Em Out." This five-year period included four million-selling albums—the last two of which, 2006's King and 2007's T.I. vs. T.I.P., hit the charts at No. 1. King single "What You Know" struck the charts at No. 3, the highest spot for a T.I. song yet.

Although 2008's Paper Trail would make T.I. a bona fide pop star, it was at the expense of some of the moments that made his music its most interesting. From a creative perspective, it was King that became his crowning achievement. The South's industry takeover had been completed; Houston had its moment, Three 6 Mafia had won an Oscar, and Lil Jon had gone from underdog to pop culture phenomenon and was on the way to obsolescence. But rather than following contemporary Southern production trends, Tip zigged when he was supposed to zag. King was built on triumphant New York-friendly Just Blaze beats, a furious show of the rapper's technical prowess, a tip (no pun intended) of the cap to his hip-hop fans. And the hoisting of a flag. Rap had a bold new ruler. — David Drake

Lil Wayne: 2004-2008

Solo Albums: Tha Carter (2004), Tha Carter II (2005), Tha Carter III (2008)
Group Albums: Like Father, Like Son (2006)
Biggest Hits: "Go D.J." (2004), "Fireman" (2005), "Stuntin' Like My Daddy" (2006), "A Milli" (2008), "Lollipop" f/ Static Major (2008),

Honestly, Wayne's contribution to "Duffle Bag Boy" is better than most of your favorite rapper's five-year runs. But just consider the degree to which Wayne was snatching spots throughout the mid-aughts. Bookended by Tha Carter and Tha Carter III, this time span had Wayne disproving the idea that a sequel is necessarily worse than its predecessor. He made each one, in multiple series, a step above the previous, as though just one or two iterations was not enough to satiate the newly dreadlocked demon-he was evolving. Both Dedication 2 and Da Drought 3 might as well have been albums, had they not been stunt acts of beat-jacking. He was rapping as though he had too many verses, and he had mixtapes upon mixtapes worth of mental overflow-a single lyric comparing either sex or weed to something altogether unrelated could not go to waste. So he'd put it on the beat for which your three phoned-in verses didn't do justice. Wayne was also steadily becoming the most requested feature, from Jay ("Hello Brooklyn 2.0") and Ye ("Barry Bonds") to Chris Brown ("Gimme That") and Destiny's Child ("Soldier"). On top of all of that, in the middle of this run, Wayne and his "Daddy" Birdman released one of the best albums of the decade, Like Father, Like Son. Everything fell into place for Wayne during those years, culminating in the crossover success of his Tha Carter III singles. From then on, it really was Wayne's world. His claim of being the best rapper alive seemed undeniable when you looked around at the rap landscape of the time, and an unlikely pop superstar had fully manifested. — Alexander Gleckman

Kanye West: 2007-2011

Solo Albums: Graduation (2007), 808s & Heartbreak (2008), My Beautiful Dark Twisted Fantasy (2010)
Group Albums: Watch the Throne (2011)
Biggest Hits: "Can't Tell Me Nothing" (2007), "Amazing" f/ Young Jeezy (2008), "Power" (2010), "All of the Lights" f/ Rihanna (2010), "Monster" f/ Jay Z, Rick Ross, Nicki Minaj & Bon Iver (2010)

The first four years of Kanye West's solo career were extraordinary: On the strength of his production chops and a Jay Z cosign alone, the buzz for his solo debut, The College Dropout, was an engine onto itself. And "Jesus Walks" silenced any doubters with a quickness. The follow-up, Late Registration, took the auteur's pop sensibilities and paired him with both brilliant collaborators (Jon Brion, Adam Levine) and career-highlight rap guest spots (Jay, Cam'ron, Lupe). In late 2007, having reached peak rap popularity, he was poised to transcended the crossover threshold, and with the September release of Graduation, and his defeat of 50 Cent in a much-hyped "first-week-sales-off," he was well on his way. The album was Kanye's self-proclaimed "stadium status" moment, a monument to the oversized, with songs that feature everything from unmistakable Daft Punk samples and Chris Martin guest spots to an outsized Gregorian-chorus style anthem ("Can't Tell Me Nothing") that's as much a an existential purpose statement as it is a radio banger. Graduation also marks Kanye's first high-profile foray into high art. Take the maximalist Takashi Murakami art that adorned the cover, for example, or the live-action cartoon Murakami made to go with the opening song, "Good Morning."

Coming off this commercial and creative victory, in late 2008, Kanye made a head-spinning move nobody could have remotely anticipated. An R&B album! One that took the predominant sonic dynamic of pop radio at that moment (an over-abundance of auto-tune) to its maximum, seemingly ridiculous limit. An entire twelve-track song cycle built around a single computer mechanism and the themes of love and loss. If the title, 808s and Heartbreak, didn't tell you everything you needed to know about the album at first, it took just one listen to realize exactly how revealing that title indeed was. The album is revered as one of the greatest sharp turns in the history of contemporary music, and yielded a few singles to demonstrate just how Kanye could manipulate the landscape of pop radio. And in 2008, where 808s detractors held steady with disdain for Kanye's new direction, they couldn't help but cop to the fact that he had successfully registered in equally significant but entirely separate ways: A ubiquitous Brit-pop R&B single "American Boy" with Estelle. A ubiquitous rap radio single with Young Jeezy ("Put On"). A ubiquitous everywhere single in "Swagga Like Us." And of course, prior to the release of 808s, a series of earth-shaking tour dates with the elaborate Glow In The Dark tour, that grossed nearly $31 million over the course of 49 tour dates.

2009 didn't see a proper album release of new material from Kanye West, but that doesn't mean he wasn't out there in the world, if not more than ever. Sure, he had two more singles from 808s to chart ("Amazing" and "Paranoid") which didn't do spectacularly. Yeah, there was the whole Taylor Swift thing. But there he was, on the Gaga-sampling "Make Her Say," on The-Dream's "Walking On the Moon," on the block-rocking Clipse track "Kinda Like a Big Deal," on Jay's Summer-owning "Run This Town," on the can't-walk-down-any-street-in-North-America-without-hearing-it "Forever." But as far as Kanye's solo output went, it wouldn't be until 2010 that we'd start hearing it again, and we'd hear it in a way we never had before: Starting with the war-march anthem "Power," Kanye's comeback kicked off with anger, the likes of which we had yet to hear from him before. "Runaway" got high-profile performances on Saturday Night Live and the 2010 MTV VMAs, both bold statements that also represented a first for West, a track that doubled as a concession to his egotism, typically played alone on a stage by Kanye, armed only with a sampling machine on a platform and a quickfire Pusha-T verse. Then there was the controversial clip for "Monster," an all-star roster song that pushed pop's tolerance for gothic rap further to the fringes that it ever had been pushed previously. As the singles for the full album Kanye was about to release were rolled out, so were the G.O.O.D. Friday tracks, songs that were relative toss-offs for Kanye that ranked about the best of the year (any and all argument, see: "Christian Dior Denim Flow"). And then there was the actual release of My Beautiful Dark Twisted Fantasy, less an album than a hip-hop opera, one that starred everybody from indie darling Justin Vernon to Elton John, and everyone in between. The album was hailed as a masterpiece, and given fawning reviews that assessed the album as essentially flawless.

2011 was no light load, either. Coming together with Jay Z to form what's now known as The Throne, Kanye consisted of one half of what essentially stands as the first rap superalbum, a case study in self-described "luxury rap" that started with an ornate, gilded cover designed by Givenchy creative director Riccardo Tisci, that relented for not a moment on the inside: Samples from Otis Redding and Curtis Mayfield, guest spots from Beyonce and Frank Ocean, songs that are equal measures reflective and philosophical as they are pathologically bombastic, taking on an almost religious commitment to braggadocio. The album yielded a tour with dates that ended by Kanye and Jay performing "Niggas in Paris" not once, or twice, but upwards of eight times. Sometimes more. 'Ye also found his way onto the remix for a blockbuster Katy Perry single ("E.T."), but that's an aside. So is everything Kanye West produced over these five years, the kind of musical output resume nobody on this list can even remotely lay claim to. The recency of Kanye's five-year run after Late Registration makes it difficult to tell where his first act ends and his second act begins, or for that matter, if his second act has even started yet. One thing is for certain, though: In five years, it is an indisputable fact that nobody did more to change the face of rap as a crossover genre-and not just crossover from rap to pop, or rap to rock, but rap as art-as Kanye West did beginning in 2007. — Foster Kamer

Drake: 2009-2013

Solo Albums: Thank Me Later (2010), Take Care (2011), Nothing Was the Same (2013)
Group Albums: We Are Young Money (2009)
Biggest Hits: "Hold On, We're Going Home" f/ Majid Jodan (2013), "Started From the Botom" (2013), "Take Care" f/ Rihanna (2012), "Find Your Love" (2010), "Best I Ever Had" (2009)

When Drake first hit the national scene in 2009, he was exactly what Nas declared him to be, "like fresh water right now on dry land." After the Toronto actor-turned-rapper born Aubrey Graham hooked up with Lil Wayne, he made his presence felt with his 2009 mixtape, So Far Gone and his massive hit "Best I Ever Had." Heavily influenced by Kanye West's 808s & Heartbreak, the tape sounded like a complete thought, a real album filled with mostly original production—not the sort of hodgepodge of raps over popular instrumentals that had become so popular in the post-50 Cent era.

Beyond the music, the context of that tape was crucial. 2009 saw a ton of promising new faces step unto the national scene including, but not limited to; Kid Cudi, J. Cole, Wale, and Nicki Minaj. But Drake trumped them all. If he couldn't outrap them, he could outsing them. And his unique skillset suggested he could potentially compete with his idols like Jay Z and Kanye West. It was obvious that a star had arrived, the only question that remained was whether or not this was a legend in the making.

That idea, Drake becoming a legend, seemed to be jeopardy in 2010 when he dropped his major label debut album, Thank Me Later. His debut arrived amid sky high expectations and criticisms of the #hashtag flow, his singing, and using a Blackberry during his Funkmaster Flex freestyle. Though Drake weathered the storm-the album spawned four Top 40 singles and sold over 1.5 million copies-it didn't feel like quite the ultimate victory it should have been. The hits were there, but the album lacked the overarching feel that made So Far Gone such an event.

But Drake silenced his critics in 2011. He claimed the year as his own early on, with a pair of singles, "Dreams Money Can Buy" and "I'm On One" (we'll never understand why he gave that one away to DJ Khaled.) Come fall, he unleashed the album that stands as his masterpiece, the sprawling, overtly ambitious Take Care. Sure enough, this album proved Drake was all that he'd claimed to be. It encompassed the full scope of his talent, the rapping, the singing, the writing, the fearless belief that hip-hop could incorporate more types of distinctly "non-rap" elements than it ever had before—pop, R&B, emo, "yacht-rock" stylings. Drake, even many of his detractors were forced to admit, was worth the hype. "Fuck you all, I claim that whenever/I change rap forever," he said on "Lord Knows." Even if you hated him, you had to admit he was right.

After that, all bets were off. Drake had found the sweet spot between celebrity and artistry, between chart hits and album cuts, between singing and rapping, between celebrity and artist. In 2012, he played like a Jordan, a Kobe, a Lebron, choosing his spots by popping up every so often on hits, he was controling the game without taking many shots. He's carried that momentum into this year (into right now, in fact). His third album, Nothing Was The Same, is another powerful statement: carefully-conceived, exquisitely executed, exuberantly recieved. He's still scoring hits on the regular, his celebrity is still growing, and he's become better at managing his brand, his narrative, and the pressures of fame. Even his haters seem to be getting tired of hating. The question is no longer whether he'll fulfill his promise, it's when he's gonna fall off. — Insanul Ahmed