The 50 Best Debut Rap Singles

Before you read any further, answer this: What was 50 Cent’s debut single?

If you replied “Wanksta,” you'd be wrong. Maybe you answered “How to Rob,” which will earn you an E for effort. In 1997, under the guidance of the iconic Jam Master Jay, a young Curtis Jackson actually pressed up vinyl for what would be his debut single, "The Glow." It didn’t go platinum, it didn't land him a lucrative label deal, and it didn't get heavy rotation on Hot 97. It was a modest tune, with Jackson rhyming over a funky Change sample that will bring more comparisons to Janet Jackson’s “All For You” than “Many Men.” None of his later success can change the fact that this was 50 Cent’s debut single.

The truth of the matter is very few rappers come out the gate with a sure-fire record. Some put out decent cuts that hold a bit of merit (Cam'ron's "Horse & Carriage") while others dropped flat-out duds (Mobb Deep’s “Peer Pressure). It was three years after the release of “Replacement Girl” that Canada’s biggest rap export was able effectively communicate his talent. Hell, even one of the greatest rappers, Jay-Z, couldn’t find traction with his early releases.

None of these examples made this list, nor should they. We should also note that a song qualifies as a single if it was properly released by the artist in some promotional form, whether that was vinyl, cassette, maxi-CD, iTunes or a music video; whichever came first. So while you can thank Carson Daly for introducing you to Eminem, the Detroit MC released a song prior to “My Name Is” that was arguably as important to his career. That record did make the cut, along with 49 others. These are the 50 Best Debut Rap Singles of all time...

RELATED: The 50 Best Rapper Mixtapes
RELATED: The 100 Greatest Hip-Hop Beats of All Time

50. The Sugarhill Gang "Rapper's Delight" (1979)

Producer: Sylvia Robinson
Album: Sugarhill Gang
Label: Sugar Hill

The one that started it all. "Rapper's Delight" wasn't the first song to feature rapping but it was the first widely popular rap song. Yet, for all the talk about how "real" rap used to be, it's important to remember that Oliver Wang once called this song what it really is, an "inauthentic fabrication."

The song wasn't recorded by the prominent rappers of the era, instead it was put together label owner Sylvia Robinson, who wanted to cash in on then burgeoning rap culture. She found a couple of around-the-way dudes to rap, found a couple of musicians to play Chic's "Good Times" for 15 minutes straight, and put together a song that changed the world. And despite it all, "Rapper's Delight" is a great rap song, one that still gets burn today. —Insanul Ahmed

49. Styles P "Good Times" (2002)

Producer: Swizz Beatz, Saint Denson
Album: A Gangster and a Gentleman
Label: Ruff Ryders, Interscope

Leading up to release of his solo debut album, Styles P was known for being a gangster and a gentlemen, but not really a stoner. Although he had the streets on lock, he wasn't known as a hitmaker, either. And way more people were checking for Jada's solo than they were for his.

But that all changed when P dropped "Good Times." Swizz Beatz, who wasn't known for sampling, blessed the track with a sample from Freda Payne's interpolation of "I Get High (On Your Memory)." The beat smacked out of speakers, Styles laced his verses with that raw uncut, and SP the Ghost scored a Top 40 hit before bandmate Jadakiss did. —Insanul Ahmed

48. Ghostface Killah f/ Raekwon "Motherless Child" (1996)

Producer: RZA
Album: Ironman
Label: Razor Sharp, Epic Street

Most of the praise for the first batch of Wu-Tang solo records goes to GZA and Raekwon for their landmark debuts. People tend to forget that Ghostface's debut is right up there too. Granted, it's not because of Ghost. At the time, he had perfected his storytelling skills but not his personality. Nor was it Raekwon and Cappadonna, who hold it down on all fronts throughout their various features.

No, Ghost's true debt was to RZA. The Abbot's production had grown by leaps and bounds in the years leading up to Ghost's first solo venture. Originally appearing on the Sunset Park soundtrack, "Motherless Child" is one of RZA's illest soundscapes. Built using two O.V. Wright samples ("Motherless Child" and "Into Something (I Can't Shake Loose)") the beat built suspense and pain, the perfect backdrop for Tony Stark's tale of a corner thug who got caught up in senseless violence. —Insanul Ahmed

47. Xzibit "Paparazzi" (1996)

Producer: Thayod Ausar
Album: At the Speed of Life
Label: Loud, RCA

French composer Gabriel Urbain Fauré's processional Pavane (debuted itself in 1887) provides the haunting base for Xzibit's breakthrough single, "Paparazzi." The beat was so well received that it was later used for a closing montage in an episode of The Sopranos.

Produced by Thayod Ausar, the track introduces the Detroit-born, L.A.-based rapper as an MC's MC. X to the Z calls out fakes—zeitgeisty in 1996—and pushes himself from Likwit Crew member cameo glory to solo stardom. The song, which was featured on At the Speed of Light, wouldn't be Xzibit's last hit, but it's certainly had greater staying power than most of his subsequent recordings. Still, the irony of the line "Either you're a soldier from the start/Or an actor with a record deal tryin' to play the part," shouldn't be lost on Xzibit fans who've seen him in more movies than albums in recent years. —Nick Schonberger

46. Apache "Gangsta Bitch" (1992)

Producer: A Tribe Called Quest
Album: Apache Ain't Shit
Label: Tommy Boy

Although we prefer the comic tunes and political message of "Kill D White People," (we still haven't forgiven them for Snow) Apache's debut single, “Gangsta Bitch,” was the only song of his to have a lasting impact.

Produced rather randomly by A Tribe Called Quest, “Gangsta Bitch” isn’t meant to be taken that seriously—after all, his album was titled Apache Ain’t Shit. The girl described in the song isn’t far removed from the girl Biggie describes on “Me and My Bitch,” and the ending of Apache’s tale isn’t far removed from Biggie’s tale. Still, we want us an gangsta bitch so we can buy her an AK for Valentines Day. Ahh, young love. —Insanul Ahmed

45. Black Star "Definition" (1998)

Producer: Hi-Tek
Album: Mos Def And Talib Kweli Are Black Star
Label: Rawkus

In the late '90s, Blackstar provided an alternative to the popular gangsta rap narratives of the time, which had gone from "keeping it real" to keeping it too damn real in the wake of Biggie and 2Pac's deaths, and jiggy rap, with Puffy and Bad Boy running radio. It was relieving to see a conscious underground act like Blackstar find a way to shine on "Definition" while blasting with accurate assassin shit on the mic.

Ironically, even though Mos Def and Talib were seen as the alternative to the Shiny Suits and the sample-ridden tunes of Puff Daddy, they essentially followed the same formula by sampling an '80s rap classic (BDP's "The P Is Free") for "Definition." And it worked. According to Kweli, Funk Flex started playing the song on Hot 97 and helped the duo get buzzing. —Insanul Ahmed

44. Tha Dogg Pound f/ Snoop Doggy Dogg "What Would You Do" (1994)

Producer: Dat Nigga Daz, Dr. Dre
Album: Murder Was the Case Soundtrack
Label: Death Row, Interscope

Once Dre and Snoop kicked down the door, shifting the sound of West Coast hip-hop with The Chronic, it was the crew's turn. Daz and Kurupt spent much of the two years following Doggystyle's release working on—that's right—The Funky Headhunter for Hammer, but once they finally hit the scene, Snoop's Dogg Pound compatriots weren't holding back.

It might seem quaint now, but at the time, West Coast gangster rap was a volatile setting. "What Would You Do," which appeared on the soundtracks to both Murder was the Case and Natural Born Killers, seemed to threaten to enflame a situation that already felt like a powder keg. The song rode an uptempo G-funk beat produced by Daz and Dre, and explicitly sent shots in each and every direction, including at Eazy E, who initially provoked the group on "Real Muthafuckin' Gs." Eazy would respond in kind over the same instrumental later that year. —David Drake

43. LL Cool J "I Need A Beat" (1984)

Producer: Rick Rubin
Album: Radio
Label: Def Jam

"I Need a Beat" wasn't just LL Cool J's debut; it was Def Jam's, too. In the wake of the success of T La Rock's "It's Yours," Rick Rubin's dorm room was inundated with demo tapes, and among them was LL's. After the Beastie Boys' Adam Horovitz discovered LL among the pile, Rubin called him up and invited him over. "I Need A Beat" was recorded soon after.

Minimal and driven entirely by a drum machine, the song epitomized the radical new aesthetic Rubin and Russell Simmons had pioneered, emphasizing the spirit of live hip-hop, rather than worrying about its disco source material. But with Run-D.M.C., Rubin and Russell had scored a deal with Profile Records; determined to have more control over the process, the two budding entrepreneurs released the record under the name Def Jam. It quickly sold 100,000 copies, and history was made. —David Drake

42. Leaders of The New School "Case of the P.T.A." (1991)

Producer: Cut Monitor Milo
Album: A Future Without A Past
Label: Elektra

Leaders of the New School's legacy has been dwarfed by that of group member Busta Rhymes, but the group had an accomplished career in its time that goes well beyond the "Scenario" guest spots that stole the show on Tribe's Low End Theory.

Released the same year as that album, L.O.N.S.'s "Case of the P.T.A." was a play on the group's name. Over a jazzy irreverent Ramsey Lewis sample, the trio tossed back and forth high school tribulations about dealing with parents and teachers while trying to play pranks and score with the ladies.

Compared to the rap that would come soon after, there's an innocence about it. Not that it's wholesome, exactly—Charlie Brown the class clown ends up in a courtroom by the end of his verse—but the lighthearted approach to the subject matter definitely feels of its era. —David Drake

41. Tim Dog "Fuck Compton" (1991)

Producer: Ced Gee
Album: Penicillin on Wax
Label: Ruffhouse

The East Coast/West Coast beef had its roots in a number of different places, but Tim Dog's "Fuck Compton" was the first to unapologetically launch into musical warfare. He had a point; New York had been overshadowed nationally by the commercial success of the West Coast in the early '90s, and record labels were flocking to Los Angeles to see if they could replicate the runaway success of N.W.A. It was Tim Dog's arrogance and imperiousness that made the record so important; it may not have charted, but it definitely provoked a reaction, inspiring return fire from Compton's Most Wanted, DJ Quik, Dre, Snoop, Tweedy Bird Loc, and others. The song marked the beginning of the East Coast hardcore revival that wouldn't really take hold until the emergence of Wu-Tang a couple years later, when street rap gained a foothold on both sides of the map. Rest in peace Tim Dog. - David Drake

40. The Beatnuts "Reign of the Tec" (1993)

Producer: The Beatnuts
Album: Intoxicated Demons: The EP
Label: Relativity, Violator

No single group better expressed the party and the bullshit ethos quite like this crew from Corona, Queens. The Beatnuts tended to focus on a couple distinct subjects: sex, drugs, booze. But most importantly, they had that hard-nosed gangster swag down pat.

It helped that they swiped a searing guitar line from Black Sabbath, which, when wed to a breakbeat worth sagging your Girbauds to, gave the song a swaggering power. Yeah, he took the ill shit, kid, he looped it, and threw atop some Sadat X for one of the catchiest call-and-response hooks in hip-hop history. When they pop the trunk, hit the deck.... —David Drake

39. Puff Daddy f/ Mase "Can't Nobody Hold Me Down" (1997)

Producer: Carlos "Six July" Broady, Nashiem Myrick, Puff Daddy
Album: No Way Out
Label: Bad Boy

Puff Daddy was no newbie to the game when he released his debut single from No Way Out. He was already a successful and established songwriter, producer, and label owner before he became a performer himself. Known as the man behind larger-than-life East Coast rap royalty Notorious B.I.G., Puff Daddy was finally ready to step out into the spotlight in a different way in January 1997, when he released "Can't Nobody Hold Me Down," featuring Ma$e.

The song, which features a slowed down version of Grand Master Flash and The Furious Five's hit song "The Message" and an interpolation of Matt Wilder's 1983 "Break My Stride" for the chorus, climbed to the No. 1 spot on the U.S. Billboard Hot 100 and stayed there for six weeks.

Puffy took this time to flex yet another talent and show that he was more than just a hype man or professional ad-libber, he was still the slick talker rapping about the ultimate come up. "Can't Nobody Hold Me Down" was more than just a song for Puffy, it was also his declaration as a multi-talented threat to the music industry. —Tannis Spencer

38. Redman "Blow Your Mind" (1992)

Producer: Erick Sermon, Reggie Noble
Album: Whut? Thee Album
Label: Rush Associated

From the jump, Redman was one of the most rambunctious hooligans to ever grab the mic. He didn't recite rhymes, he bombarded you with them. The beat to his debut single was as chaotic as his flow, using a whopping seven samples from everyone from Zapp to James Brown (good thing he shouted him out in the song to avoid getting sued, though we're not sure that holds up in court).

The most memorable lines weren't even in English, they were in Korean, as Red flipped foreign language-style with the help of Korean Jive Records employee Sophia Chang. Just another reminder that with the Funk Doc, you never know what's coming next. —Insanul Ahmed

37. Missy Elliott "The Rain (Supa Dupa Fly)" (1997)

Producer: Timbaland
Album: Supa Dupa Fly
Label: The Goldmind, EastWest, Elektra

Armed with an Ann Peebles sample and Timbaland at her side, Missy "Misdemeanor" Elliott waltzed onto the rap scene with an out-of-this-world style. "The Rain" is best remembered for its Hype Williams-directed video, but take a listen to it today and you can still hear how startlingly original it was and still is.

The strings on the beat hit like raindrops on your window pane as Missy weaves her way through the track. For all the talk about how lyrics have declined in hip-hop, everyone should peep her playful words ("Beep beep, who got the keys to the Jeep? Vroom!")—and be reminded that even in hip-hop, sometimes the lyrics just aren't the main point.

Missy was always an anomaly. Like Busta Rhymes and ODB, she was a true original who was genuinely left field. Ironically, in the late aughts, as weirdos became more in vogue in hip-hop, Missy was no longer active in the scene even though her influence wasn't hard to see. —Insanul Ahmed

36. Kid Cudi "Day 'n' Nite" (2007)

Producer: Dot da Genius, Kid Cudi
Album: Man on the Moon: The End of Day
Label: Fool's Gold

Inspired by the Geto Boy's "Mind Playing Tricks On Me," Kid Cudi hit the scene with a stoner anthem that shot him to stardom and inspired an instant cult following. The slow, prodding instrumental provided by long time friend Dot Da Genius set a dark mood, but Cudi's gentle vocals carried the record.

Cudi painted in broad strokes; he didn't tell a story per se but instead narrated the life of the lonely loner, Mr. Solo Dolo. Of course, Cudi was essentially talking about himself. Well, except for the whole "A silent sleeper you won't hear a peep," since Cudder has often spoken about his frequent night terrors as a child. —Insanul Ahmed

35. M.O.P "How About Some Hardcore" (1993)

Producer: DR Period
Album: To The Death
Label: Select

There was always something comical about M.O.P.'s brand of hardcore, an attempt to push aggro New York street rap to its logical endpoint. What better way to kick off that career than the knowing title to their debut single, the ironically-named "How About Some Hardcore"?

The title offers the notion as if they were proposing dinner plans, rather than pushing the envelope on the grimiest of street music. Of course, by the standards that Lil' Fame and Billy Danze would later reach—particularly the apex of their sound, "Ante Up"—"How About Some Hardcore" was funkier and friendlier, if such a thing can ever be said about the duo.

Although they do nothing but mean-mug and ice grill in the video, there's still something welcoming about the beat Fame and Danze elected as their breakthrough track. Perhaps it aided in its placement on the House Party 3 soundtrack. —David Drake

34. T La Rock & Jazzy Jay "It's Yours" (1984)

Producer: Rick Rubin
Album: N/A
Label: Def Jam

This was the record that first drew Russell Simmons' attention to a producer named Rick Rubin. Ironically, "Sucker MCs," co-produced by Simmons, first inspired Rubin to create it. Rubin had borrowed a TR-808 drum machine from the Beastie Boys' Adam Horovitz, and tried to get the Treacherous Three to rap over it. But the Treacherous Three could only record exclusively for Sugar Hill, so group member Special K recommended Rubin get in touch with his older brother, Terry "T La Rock" Keaton.

The record was born in an attempt to give equal billing to T La Rock, whose lyrics were unexpectedly multi-syllabic and complex for the era, and DJ Jazzy Jay, who scratched in between each verse. With stratosphere-rending scratches and gut-wrenching kick drums, the song was a sonic masterpiece, and ultimately proved to be the catalyst for the friendship of Russell Simmons and Rick Rubin, as well as the creation of Def Jam Records. —David Drake

33. The Lady of Rage "Afro Puffs" (1994)

Producer: Dr. Dre
Album: Above the Rim: The Soundtrack
Label: Death Row, Interscope, Atlantic

After throwing her weight around on The Chronic and Doggystyle, Death Row's token female rapper Lady of Rage was perfectly poised to become the queen of hip-hop's g-funk era. And she finally got her shot in the summer of '94, when her solo debut "Afro Puffs" was released as the fourth single from the double platinum Above The Rim soundtrack.

Many women had attempted to tackle the rugged sound of West Coast gangsta rap, but Rage—a native of Farmville, Virginia—commanded respect like no other: "Now I'm hittin' MCs like Haaaadouken!/Ain't no doubt about it, I'm the undisputed." Her precise flow fell perfectly in the pocket of the neck-snapping Daz-and-Dre beat, which was remixed for the radio using the same Johnny "Guitar" Watson sample that Biggie had rapped over earlier that year on Mary J. Blige's "What's The 411 (Remix)." With an ominous video that styled her as a brolic blaxploitation heroine—leather, cowrie necklace, the titular hair style—Rage had all the makings to be Suge's next star.

Sadly, "Afro Puffs" was overshadowed by another female rapper who blew up by copying the Death Row sound: Da Brat's "Funkdafied" went platinum just as Rage was starting to climb the charts. But even though Rage will always be remembered as a one-hit wonder, "Afro Puffs" stands as the last truly perfect single from Death Row's original roster. Or, in the more succinct words of the Doggfather: "Snoop Doggy Dogg still don't love a hoe—but you gotta give credit where credit's due." - Brendan Frederick

32. Smif-N-Wessun "Bucktown" (1994)

Producer: Mr. Walt & DJ Evil Dee of Da Beatminerz
Album: Dah Shinin'
Label: Wreck

In 1994, Smif-N-Wessun brought the ruckus to the underground with its debut single “Bucktown.” It was a Brooklyn anthem to the fullest, with Tek and Steele stomping the mean streets of BK with their fingers on the trigger. The song did more than just make Smif-N-Wessun underground sensations. It crafted a fuller aesthetic for the entire Boot Camp Clik. No crew used gun metaphors quite as often as they did, and “Bucktown” was a reminder that it was rooted in the reality of life live in the county of Kings. —Insanul Ahmed

31. Method Man "Bring the Pain" (1994)

Producer: RZA
Album: Tical
Label: Def Jam

[Ed. Note—"Method Man" cannot be considered Tical's debut single as it was billed as a Wu-Tang Clan song (despite being a solo cut), served as a b-side to "Protect Your Neck," and was featured on Enter The Wu-Tang: 36 Chambers.]

In 1993, you could make the case that Method Man was the the King of New York. The Wu-Tang Clan had invaded the rap game with "Protect Ya Neck" and dropped an all-time classic with 36 Chambers. The clan was in the front but it was Tical who was the clan's frontman. His microphone technique and rugged personality were established on "Method Man," making him the breakout star of the group.

"Bring The Pain" picked up from where "Method Man" left off, and even continued the game of "Torture" that Meth and Rae were playing on the skit before "Method Man." RZA's spooky instrumental set the tone, yet it was Method's lyrical dexterity that made the track what it is. Johnny Blaze's madcap style constantly shifted between snappy rhymes ("In your Cross Colour clothes you've crossed over/Then got Totally Krossed Out and Kris Kross") to over-enunciated exposition ("MOVING ON YOUR LEFT!").

2Pac later lifted Meth's opening lines for the hook to his song, "No More Pain," but it was Chris Rock who made the title iconic: His career changing comedy special borrowed the song's title. —Insanul Ahmed

30. De La Soul "Plug Tunin'" (1988)

Producer: Prince Paul, De La Soul
Album: 3 Feet and Rising
Label: Tommy Boy

The original version of "Plug Tunin'" introduced both Prince Paul's kitchen-sink production style and De La's lyrically experimental approach. The very first recording the group created together, the song existed in a pre-Prince Paul format. When Paul heard the song, he told us in an extensive interview, he jumped at the chance to remake it. "It blew my mind," he recalled. After he rearranged the beat and added new samples, the song became De La's first track, and the group's first song to make it to radio. "It's such an odd record, nothing predated that, and it sounds like throwing whatever in the wind," Paul told us. "You didn't know where it was going to land. For touchy radio world back then to play that record is when I knew I won." - David Drake

29. EPMD "It's My Thing" (1987)

Producer: EPMD
Album: Strictly Business
Label: Fresh

After the whirring chopper blades that open EPMD's debut single, in comes The Whole Darn Family's "Seven Minutes of Funk," which the duo swiped after hearing DJ Red Alert play the break all the time. What EPMD added—other than the helicopter effects—was a confident nonchalance and lazily confident punchlines: "And if it gets warm take off the hot sweater/And if you want some water, I'll get you a cup/And if you don't want it, then burn the hell up." In an interview with Complex last year, Sermon explained how "It's My Thing" also marked ground zero for Erick Sermon the producer, when Special K and Teddy Ted mixed in Marva Whitney's "It's My Thing" directly through turntables. The song epitomized EPMD's approach: big, hooky samples and a casually confident rap style that would very quickly transform the duo into East Coast hip-hop stars. -David Drake

28. Rick Ross "Hustlin'" (2005)

Producer: The Runners
Album: Port of Miami
Label: Slip-n-Slide, Def Jam, Poe Boy

Miami went major in 2006 when William Leonard Roberts II stepped into the spotlight and assumed his bombastic rap persona, Rick Ross. Produced by an almost equally unknown duo, Orlando's The Runners, the track functioned as an anthem for ambition, vaulting the Floridian rapper into the national conversation and giving coke rap new legs. The mix of South Beach glamour and Carol City grit took root over a beat deservedly characterized as "cinematic," enough to inspire one of Wayne's best efforts on the much celebrated Dedication 2. Ross, no doubt, owned the moment—his motivational mantra applicable to whipping work or simply driving to a regular 9-5—and when Jigga and Jeezy hopped on their Def Jam brethren's remix, Rozay's seemingly instant rise was solidified. - Nick Schonberger

27. Ol' Dirty Bastard "Brooklyn Zoo" (1995)

Producer: Ol' Dirty Bastard, True Master
Album: Return to the 36 Chambers: The Dirty Version
Label: Elektra

Straight from the rap orphanage, ODB's solo debut confirmed what his brief appearances on 36 Chambers had hinted at: there was no father to his style. ODB simply spazzed on the track. There was an animal instinct to bars like, "In your face like a can of mace, baby/Is it burning? Well, fucking now you're learning!" The off-kilter, wheezy beat matched the unorthodox style to a t. His second single, "Shimmy Shimmy Ya" was a smash too, but "Brooklyn Zoo" was that certified funk only Dirt McGirt could deliver. RIP ODB. - Insanul Ahmed

26. Snoop Doggy Dogg "Who Am I? (What's My Name?)" (1993)

Producer: Dr. Dre
Album: Doggystyle
Label: Death Row, Interscope, Atlantic

This might be Snoop's technical "debut single" but he was already a well established star when it dropped. He first popped up with "Deep Cover" and then became the voice of West Coast hip-hop on Dre's The Chronic. Doggystyle may have been one of the most anticipated debuts in rap history, but it was essentially more of the same from Snoop.

Not that anyone was complaining. It was a must that Snoop dropped gangsta shit, but as usual Dre's production was as much a star on this track as Snoop. Dre's idolization of George Clinton is as apparent as ever here as he samples both George Clinton's "Atomic Dog" for the hook and Funkadelic's "(Not Just) Knee Deep" for the song's grinding bassline. The beat has so many more elements (additional vocals from Jewel, Dre, and Tony Green) that are easy to overlook. But the fact remains, it's still pure, unadulterated g-funk. - Insanul Ahmed

25. Black Moon "Who Got da Props?" (1992)

Producer: DJ Evil Dee of Da Beatminerz
Album: Enta da Stage
Label: Nervous

Ronnie Laws' "Tidal Wave" was the basis for the DJ Evil Dee-produced debut record from Black Moon, a trio that included Dee, Buckshot, and 5 ft. Excellerator. The song's blunted Timbs-and-hoodies aesthetic would go on to define the crew's whole catalog, although occasionally with an even less accessible sound. Black Moon were a career-long mean-mug, a humorless, unapologetically underground rap style that stuck out for its darkly monochromatic feel. They also pre-dated many similar acts—Mobb Deep, Wu Tang Clan, etc.—whose street-oriented sounds would completely realign New York into a smoggy atmosphere over the next few years. - David Drake

24. Jeru The Damaja "Come Clean" (1993)

Producer: DJ Premier
Album: The Sun Rises in the East
Label: Full Frequency Range

DJ Premier was already a hip-hop hero when Jeru the Damaja made his first splash as a solo artist, in the wake of a scene-stealing guest spot on Gang Starr's "I'm the Man" the previous year. But no one was ready for "Come Clean." The song featured a percussive beat that was so unusual some listeners suspected it wasn't a sample at all. (The song was, in fact, a sample of Shelly Manne's "Infinity"). Jeru's chest-beating performance helped the song become an underground smash, as Jeru challenged gun-clapping MCs with his "mind spray," taking a more righteous tack than most without sacrificing the feeling of threatening power: "The result's your remains stuffed in a car trunk." - David Drake

23. Kool G Rap "It's a Demo" (1986)

Producer: Marley Marl
Album: N/A
Label: Cold Chillin'

It's sort of heartwarming to hear old school rap records that really pay homage to the DJs. In the early days of hip-hop, the DJ was the most revered figure in the culture, not the rapper. Over time that dynamic changed, but in the early days of hip-hop you could still see how that factored into the way MCs rapped. Like "Eric B. Is President," "It's A Demo" highlights this relationship rather acutely. G Rap might have been a "psychopath on the phonograph" but he spent a good portion of the record paying homage to DJ Polo for his hand skills before going on to talk about himself. But in the end, it was G Rap's innovative rhymes that we all had memorized. - Insanul Ahmed

22. DJ Quik "Born and Raised in Compton" (1990)

Producer: DJ Quik
Album: Quik Is the Name
Label: Profile

Inspired and angered by a neighborhood thief who broke into his mom's house and stole his music equipment, DJ Quik penned an ode to his hometown of Compton. Although he was actually living in L.A. at the time, he was watching as N.W.A took the world by storm. He sampled "Compton's N The House" from N.W.A, along with "Hyperbolicsyllabicsesquedalymistic" by Isaac Hayes, "Hardcore Jollies" by Funkadelic, and "She's Not Just Another Woman" by 8th Day to form the funky track. His rhymes sound noticeably old school when hearing them today, but this remains one of the best hometown anthems and one of Quik's biggest hits ever. - Insanul Ahmed

21. Nelly "Country Grammer (Hot Shit)" (2000)

Producer: Jason "Jay E" Epperson
Album: Country Grammer
Label: Universal

No one talks about it anymore, but when Nelly hit the scene in 2000 he exploded like few other rappers before or since. Yes, he was the definition of a "pop rapper" but, on the low, this song is kinda hard (the hook is about a drive-by and weed smoking). It packed the wonderful irony of being sung in the tune of a clapping game often sung by children ("Down Down Baby"). Nelly's flow was notoriously difficult to decipher, not just because of his actual country grammar but because of his delivery. That didn't stop the song from becoming a Top 10 hit on Billboard and helping Nelly's debut album of the same title go diamond—a feat accomplished by only a handful of rap albums. A decade after the fact, Nelly is totally irrelevant and people act like he never even existed, but he had a moment like few others. Down, down, baby indeed. - Insanul Ahmed

20. Eminem "Just Don't Give A Fuck" (1998)

Producer: Bass Brothers, Eminem
Album: The Slim Shady LP
Label: Aftermath, Interscope

"My Name Is" might have introduced the world at large to Eminem and made him a part of pop culture's collective consciousness, but it was "Just Don't Give A Fuck" that made him an underground favorite before the fame. After struggling to find his voice on Infinite, Eminem emerged on "Just Don't Give A Fuck" with his Slim Shady persona in tow. Surprisingly, he sported a punchline laden flow, with rhymes like, "Cursing at you players worse than Marty Schottenheimer," and "I'll slit your motherfucking throat worse than Ron Goldman." But there was still the multi-syllabic lines that would later become a lyrical trait, "Extortion, snorting, supporting abortion/Pathological liar, blowing shit out of proportion/The looniest, zaniest, spontaneous, sporadic/Impulsive thinker, compulsive drinker, addict." Years later, this remains as one of Em's best songs and encapsulates the briefest of moments when he was an unknown rapper with a superstar flow. - Insanul Ahmed

19. Nasty Nas "Halftime" (1992)

Producer: Large Professor
Album: Zebrahead Soundtrack
Label: Ruffhouse

Nasir Jones grabbed the full attention of hip-hop heads by flipping similes and handling boastful overtones as a teenager on Main Source's "Live at the BBQ," but it was the lyrical declaration of "Halftime" that solidified his presence as a true force to be reckoned with.

Initially featured on the soundtrack for the 1992 film Zebrahead, and subsequently his magnum opus Illmatic, the Queensbridge MC lived up to his "Nasty Nas" moniker with unapologetic wordplay ("You couldn't catch me in the streets without a ton of reefer/That's like Malcolm X catching the jungle fever") and a seamless delivery to match. This all over a ridiculous boom bap beat from Large Professor that still blows out speakers to this day. We're not saying Busta Rhymes couldn't have done it justice, but God's Son spoke his legacy into existence with this transcendent cut. - Edwin Ortiz

18. Goodie Mob "Cell Therapy" (1995)

Producer: Organized Noise
Album: Soul Food
Label: LaFace

While the group had already made an impression on OutKast's "Get Up, Get Out," their solo debut "Cell Therapy," from the album Soul Food, was evidence that Goodie Mob was going to push the Dungeon Family sound in a different direction. Over a sparse, crackling piano lick patterned like a tango plunked at by a drunken musician, the Mob rapped about black helicopters and conspiracy theories that they made seem eerily plausible, rather than outlandish and absurd. Halfway between the unbelievable rantings of a gruff community elder and the wisdom of people who had seen far more unbelievable things actually come to pass, the track captured a sense of communal paranoia perfectly, and marked an auspicious debut for one of Atlanta's finest hip-hop groups. -David Drake

17. Biggie Smalls "Party and Bullshit" (1993)

Producer: Easy Mo Bee
Album: Who's The Man? Soundtrack
Label: Uptown, MCA

Way before Puff was in that tub spilling Mo, Biggie was getting pissy drunk at Brooklyn house parties. Yet the scene Biggie describes is more terror than triumph. He seems to have a good time since there's three references to honeys, three references to blunts, and several alcohol brands mentioned (Henny, Don Perrignon, Heineken, and even Moet) but there's nearly a dozen references to toting guns. And when a fight a breaks out at the end of the song, his worst fears are confirmed. All of this might sound like typical paranoid Biggie, but the most harrowing line of the song remains, "I hope I don't get shot." - Insanul Ahmed

16. Big Daddy Kane "Raw" (1987)

Producer: Marley Marl
Album: N/A
Label: Cold Chillin'

Big Daddy Kane's "Raw" announced the arrival of a new, singular hip-hop talent. On "Raw," Kane spit casually-dexterous rhymes over a simple drum loop (Bobby Byrd's "Hot Pants"), a proving ground for his nimble precision. Only on the chorus does the song even strike a melodic note. For Kane, the uptempo breakbeat was an opportunity to exercise flawlessness: "Genuine like Gucci, raw like sushi," Kane promised to "captivate the crowd's majority," and it would be difficult to argue that he hadn't done so. Kane's error-proof raps couldn't hide behind a hook or any other concession to pop songwriting should he slip up. It was a high-wire act, and not only did he cross the cable, he did so with effortless ease. - David Drake

15. OutKast "Player's Ball" (1993)

Producer: Organized Noise
Album: Southernplayalisticadillacmuzik
Label: LaFace, Arista

André 3000 begins, "It's beginning to look a lot like what? Follow my every step." Good advice. Even if you don't know that OutKast's debut single was intended as a Christmas song, and thus miss the cleverness of the opening turn, the first line still works as a perfect introduction to one of hip-hop's greatest groups.

From '94 to 2003, from Southernplayalisticadillacmuzik to Speakerboxxx/The Love Below we played catch up with Big Boi and Dré. With each album of effortlessly tuneful rap, the duo moved along a path fans and critics couldn't see. Like the skit on Aquemini says, "Man, first they were some pimps. Then they were some aliens or some genies—some shit. Then they be talkin' 'bout that black righteous space."

"Player's Ball" is definitely on some pimp shit. The hook is infectious, better than most pop. That's a hallmark of 'Kast's sound, the earworm. André 3000's flow is natural but far from routine—you struggled to keep up. Big Boi's verses are full of his impeccable enunciation and slickness. And the sleigh bells keep everything chill, regardless of the season. —Ross Scarano

14. Warren G f/ Nate Dogg "Regulate" (1994)

Producer: Warren G
Album: Above the Rim: The Soundtrack
Label: Def Jam, Death Row, Interscope

Warren G's best known song might be "Regulate" but his career before that record dropped would be better summarized as "overlooked." Despite being the one who introduced his friend Snoop Doggy Dogg to his half-brother Dr. Dre and teaming up with Snoop and Nate Dogg to form 213 prior to "Deep Cover," for whatever reason, Suge Knight simply ignored Warren G. What did he care? Death Row and West Coast hip-hop were dominating the rap market without him. But one man cared: Chris Lighty (RIP). The wily industry vet made moves, got Warren G on Def Jam, "Regulate" became a smash, and it scored a much needed victory for the label going through a cold moment. Meanwhile, despite all the credit we'd like to give to Warren G and his laid back flow, it was the masterful lull of Nate Dogg that made the song what it is. RIP to Nate Dogg and Chris Lighty, both legends in their own right. - Insanul Ahmed

13. Busta Rhymes f/ Rampage "Woo Hah!! Got You All in Check" (1996)

Producer: Rashad Smith
Album: The Coming
Label: Elektra

As a member of Leaders of the New School, Busta Rhymes had already established himself as an explosive, charismatic performer with an unusual energy. When it came time to introduce the rapper as a solo artist, "Woo Hah!! Got You All in Check" found him pushing in even more radically absurd directions. With a quirky melody (courtesy Galt MacDermot's "Space") and a surreal chorus (an interpolation of a moment from the Sugarhill Gang's "8th Wonder"), the song had an off-kilter, carnivalesque vibe. It was a perfect introduction to Busta, whose career for the next few years seemed to revolve around similar absurdist club-rocking; even the aesthetic of his videos was established at this point, as a newly-ascendent Hype Williams reinvented the hip-hop video with the fish-eye lens, a trick he and Busta would return to (to great creative results) in future years. - David Drake

12. Special Ed "I Got It Made" (1989)

Producer: Howie Tee
Album: Youngest in Charge
Label: Profile

Chief Keef wasn't the first 16-year-old to stunt on wax. That's how old Special Ed was when his debut LP was released; Youngest in Charge sold half a million records on the strength of his debut single "I Got It Made," a celebration of his newfound wealth and security. Over a sample of Ripple's "I Don't Know What It Is but It Sure Is Funky," the MC spit boasts that had kids across the country identifying—or wishing they could. "Make a million dollars every record I cut" he boasted, a bit unbelievably. But he lived the fantasy so others could feel it vicariously, bragging about how every other week he had a brand new car, an island of his own, and even a solid gold bone for his dog. Just imagine what his Instagram account would have been like.-David Drake

11. House of Pain "Jump Around" (1992)

Producer: DJ Muggs
Album: House of Pain
Label: Tommy Boy

We're willing to bet the yearly royalty check these guys get for the publishing on this song is something mighty sweet. How can it not be? You can't go to a sporting event without hearing this tune. Thanks to its distinctive horn sound and memorable opening lines, this song became a Top 5 hit in the US. It was a straight up funky cipher that sways between braggadocios rhymes and a call to get up and, well, jump around. Sadly, the massive hit later worked against the group and their legacy. House of Pain is often unfairly seen as a one-hit wonder even though they actually had a few other hits and most of the group's members went on to have significant, commercially successful solo careers. - Insanul Ahmed

10. Kanye West "Through the Wire" (2003)

Producer: Kanye West
Album: The College Dropout
Label: Roc-A-Fella, Def Jam

Like the way 50 Cent used his near-death experience to fuel his career, Kanye made his nearly fatal 2002 car crash the subject of his debut single. He sampled Chaka Khan's 1985 single "Through the Fire" in his then trademark sped-up soul sample style and it became the first of his many solo hits. The song did more than just retell the story and aftermath of the crash; it helped Ye establish his refreshing humorous but honest persona. He famously recorded the song while his jaw was still wired shut but that only helped mask the choppy but admirably lackluster flow he had back in those days. It's a disservice to just listen to this song on its own; everyone (especially aspiring artists) ought to consider why dude fell asleep at the wheel and ended up having such a harrowing story to tell: He was working so damn hard. - Insanul Ahmed

9. Audio Two "Top Billin'" (1987)

Producer: Daddy-O, Audio Two
Album: What More Can I Say?
Label: First Priority

Pop quiz: What are the names of the two members of Audio Two? Give up? Try Gizmo and Milk Dee. If you're in a certain age bracket, those names might not ring a bell. But trust, you know Milk Dee's voice and lyrics even if you've never heard this song. And no not just because 50 got the "I Get Money" sample from this song. Not because it's not relevant but because it's too obvious. Instead, we'd just like to point out how everyone from Wyclef to Luniz to 2Pac to Wale has either sampled or quoted this song. Audio Two never had another significant record, but when your debut single is as good as this, it's hard to complain. - Insanul Ahmed

8. Naughty By Nature "O.P.P." (1991)

Producer: Naughty By Nature
Album: Naughty by Nature
Label: Tomy Boy

Inspired by a neighborhood drug dealer who claimed he was "down with O.P.M." (Other People's Money), Naughty By Nature made one of the biggest rap crossover smashes ever. Like most of Naughty's biggest songs, it's celebrated for an incredibly catchy hook, as well as popularizing the phrase O.P.P. What's important to remember is that the word "pussy" is never actually said in the song, nor is any other curse word. Naughty found a balance of street tough and pop appeal layered over a jumpy Jackson 5 sample that catapulted them into mainstream success. The rest is party rap history. - Insanul Ahmed

7. Cypress Hill "How I Could Just Kill a Man" (1991)

Producer: DJ Muggs
Album: Cypress Hill
Label: Ruffhouse, Columbia, SME

Released as a b-side to "The Phuncky Feel One," "How I Could Just Kill A Man" introduced one of the most distinctive and beloved groups in rap history. The song features what would become Cypress's signature sound: Muggs' funky, stumbling sample-based beats, and the yin and yang duo of Sen Dog and B-Real.

Before they hit the national scene, the running joke in the group was that B-Real's lyrics were great, but his voice wasn't. He found a workaround and started rapping with a zany, cartoonish voice. It was the perfect vocal foil for Sen Dog's baritone (which he referred to as "psycho-beta") and Chuck D styled delivery. More importantly, B-Real's voice helped sell the idea that he was actually insane in the membrane and might really catch a homicide case. "Kill a Man" had a slow burn, but when it hit, rap had one of its great cult groups. - Insanul Ahmed

6. Dr. Dre f/ Snoop Doggy Dogg "Deep Cover" (1992)

Producer: Dr. Dre
Album: Deep Cover Soundtrack
Label: Epic

Fittingly, the launch of Dr. Dre's solo career is best remembered for his contributions as a producer and A&R, not as a rapper. With N.W.A in his rear view, Dr. Dre went solo on that ass in the early '90s. Before his journey took flight, his half-brother Warren G hipped him to the sounds of his boy Snoop Doggy Dogg. Dre brought Snoop along for the ride and introduced the world to Calvin Broadus.

On "Deep Cover," Snoop hadn't honed in on his persona just yet, but his unique voice and delivery made him electrifying on the mic. Meanwhile, Dre supplied Snoop with a haunting backdrop, one better suited as the soundtrack to walking down a dark alley than a movie. Dre and Snoop proved a formidable duo and "Deep Cover" laid the groundwork for their seminal classics The Chronic and Doggystyle. - Insanul Ahmed

5. Eric B. & Rakim "Eric B. Is President" (1986)

Producer: Eric. B
Album: Paid in Full
Label: Zakia, 4th & Broadway

In recent years the discussion about this song has been all about who really produced it, Marley Marl or Eric B. We get why hip-hop heads would fret over the credits, but we'd rather concern ourselves with the grooves and rhymes. Rakim, the greatest rapper to ever rap about rapping, set the tone right away on this track, bursting out with, "I came in the door, I said it before/I never let the mic magnetize me no more." It's more than just the beats and rhymes though, it was Rakim's delivery that made him so exceptional: In an era when it felt like every rapper was competing to outshout the other, The 18th Letter's flow was smooth as syrup and as calm as the eye of the storm. That made him revolutionary then, but peep how well his music has aged compared to his contemporaries now and keep following the leader. - Insanul Ahmed

4. Run–D.M.C. "It's Like That" (1983)

Producer: Russell Simmons, Larry Smith
Album: Run–D.M.C.
Label: Profile

Often credited with ushering in the new era of rap music, Run-D.M.C. were revolutionary from the moment they dropped this gem. Produced by Jam Master Jay, Russell Simmons, and Larry Smith, this was an abrasive anthem for the bubbling new hip-hop community that was ready to address what was going on in the streets. The song was originally intended for Kurtis Blow, but with some persuasion Run convinced Russell and Larry to allow the young trio to make a demo. "It's Like That" became the group's debut single and boasted an aggressive percussion section accompanied by Run and D.M.C's animated story-telling. It was the launching pad for one of the most important rap acts ever. - Tannis Spencer

3. Eazy-E "Boyz-n-the-Hood" (1987)

Producer: Dr. Dre
Album: N.W.A. and the Posse
Label: Ruthless

This song wasn't even meant to be an Eazy-E song, much less his legendary debut. It was penned by Ice Cube for a group called H.B.O. on Ruthless Records but they passed on it. Their loss; the world's gain. Eazy might not have been the best technical rapper, but he was equipped with a zany voice that could deliver lines like, "Cruising down the street in my '64" in a way that pretty much no other human on the planet could. And although it wasn't the first song Dr. Dre produced, it was one of his first truly great beats oufitted with an unforgettable loop. N.W.A would go on to change the world, but this was the track that began their rise to the top. - Insanul Ahmed

2. Boogie Down Productions "South Bronx" (1986)

Producer: Ced Gee, Scott La Rock, KRS-One
Album: Criminal Minded
Label: B-Boy

RIP Mr. Magic. If it wasn't for him who knows where KRS-One would be right now. Back in the mid-80s Mr. Magic was one of the biggest radio DJs. Up-and-coming rap act Boogie Down Productions ran up on him to get him to hear their demo but for whatever reason, Mr. Magic dismissed BDP. KRS-One and Scott La Rock decided to take their frustrations out on Magic's Juice Crew and MC Shan, whose Queens-repping record "The Bridge" ruled the airwaves. Riled up, KRS misinterpreted the lyrics of "The Bridge"—assuming it was saying that hip-hop started in Queensbridge as opposed to the Bronx—and unleashed "South Bronx," an all out diss record that spawned the infamous Bridge Wars. The importance of "South Bronx" cannot be overstated. From the opening cowbells through the bleating horns and KRS-One's menacing rhymes to Kris's send-off ("Fresh for '86, you suckas") it's a hip-hop classic from head to toe. It's not just a classic diss song (or song period); it set the gold standard for what a hip-hop diss record could be. Even if the scope of the beef has (unfortunately) been surpassed in rap history, the debut record has not. - Insanul Ahmed

1. Wu-Tang Clan "Protect Ya Neck" (1992)

Producer: RZA
Album: Enter the Wu-Tang (36 Chambers)
Label: Loud

It's difficult to overstate the alien invasion-like effect Wu's debut record had on hip-hop. Prior to the conception of the Wu-Tang Clan, members of the group had dabbled in solo endeavors (RZA as Prince Rakeem, GZA as The Genius, and the initial group as Force of the Imperial Master) before recording what Method Man once described to Complex as, "the posse cut." And a posse they were, attacking the song with a distinct synergy that separated them from everything else on rap's radar. Whether it was Inspectah Deck's metaphoric opening bars, ODB's ruthless growl or RZA's hail mary of a verse, "Protect Ya Neck" was as focused as it was lethal, and each member made their mark in true Shaolin fashion; flawless execution. - Edwin Ortiz