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Hip-hop has never been a stranger to the unsavory elements of American life. Drug dealers and dope fiends, pushers and prostitutes, stick-up kids and corner boys have all found a home within the stories told in rap music. However, one particularly seedy character has nearly gone extinct within the music these days—the pimp.
The origins of pimp rap can be traced back to the gritty, pulp fiction of influential author and ex-pimp Iceberg Slim in the late 1960s and 1970s. The colorful, no-nonsense anti-heroes who populated Slim’s novels such as Pimp, Trick Baby, and the autobiographical The Naked Soul Of Iceberg Slim would help to popularize pimp culture in broader American life. Soon, blaxploitation films of the 1970s such as Super Fly, The Mack, and Willie Dynamite would draw inspiration from Iceberg Slim further highlighting the pimp in pop culture.
A few short decades later, pimp culture would be widely represented in the music and videos. Artists such as Snoop Dogg, Ice-T, Slick Rick, and Too $hort would adopt many of the mannerisms, fashion, and slang of the pimp, helping mainstream one of America’s most notorious criminals. Although not always explicitly about the profession of pimping itself, pimp rap always managed to capture the job’s attitude and rarefied funk.
These days, however, “the pimp” is a bit of an endangered species within rap. While misogyny and female objectification are as prevalent as ever in rap music, few artists explicitly position themselves as the heir apparent to Iceberg Slim. As a shrinking music industry increasingly relies on corporate branding of their artists to turn a profit, it’s easy to understand why pimp rap is disappearing. Few companies seem willing to associate with something as inherently ugly as pimp culture when a softer, gentler form of rap is so popular these days. The reign of the Great American Pimp might be gone forever, but not forgotten. We look back today at a list of hip-hop’s most well-known players within the history of the genre.
B.J. Steiner is a writer living in New York. Follow him @DocZeus.
Spoonie Gee
Debut: 1979
If you analyze the artistic DNA of every single rapper on this list, you’ll notice that they all share a common ancestor: Harlem lover-rap godfather, Spoonie Gee. Spoonie was a true original who brought the art of love and sex rap to the game during the culture’s infancy. Old school legend Kool Moe Dee wrote in his book, There’s A God On Mic, that Spoonie was “to hip-hop as Barry White and Teddy Pendergrass were to R&B.” As a true pioneer in hip-hop culture, old school classics like “Spoonin’ Rap,” “Love Rap” and “The Godfather” are considered canonical. Spoonie’s silky, smooth style built a foundation upon his prowess with the ladies that still remains influential to this day.
Ice-T
Debut: 1982
Rap music’s original gangster was also one of the first MCs to explicitly detail the pimp game on wax. With a flashy player persona, and cold calculated rhymes about the gritty side of street life. Ice-T is widely recognized as the pioneering godfather of both West Coast hip-hop and gangster rap.
Starting with his 1987 debut album, Rhyme Pays, Ice’s tales of dangerous criminals, fast money, and fast women were not only informed by his admiration of reformed pimp and author, Iceberg Slim, but directly by his experiences as a real-life pimp as an enterprising young man in Hawaii after a stint in the army. Songs such as “Somebody Gotta Do It (Pimpin’ Ain’t Easy)” “High Rollers,” and “6 N The Morning” were sly morality tales that not only displayed his knowledge of the pimp life but showcased a sense of social consciousness that would often go ignored by critics.
Over three decades into his storied career, Ice-T remains a celebrated, crossover icon in hip-hop culture as he’s become an admired actor, author and filmmaker. Ice-T proves that even a pimp can find redemption.
Slick Rick
Debut: 1982
Rocking an eyepatch and sporting enough gold to be the envy of an ancient Egyptian prince, few artists in any genre of music have a look quite as iconic as Rick the Ruler himself. Debuting as the featured vocalist in Doug E. Fresh’s Get Fresh Crew in the early 1980s, the British-born Slick Rick quickly proved to be one of the most enduring acts in hip-hop history. MC Ricky D’s sly British accent and masterful ability to craft hilarious story rhymes gave birth to some of hip-hop’s most indelible songs including “The Show,” “Children’s Story,” “La Di Da Di” and the controversial pimp-by-numbers anthem, “Treat Her Like A Prostitute.”
While a five-year prison stint for a 1990 club shooting started a series of legal issues (including a drawn-out immigration battle) that effectively curbed his career’s momentum, Slick Rick would persevere to win his freedom and become one of the most venerated icons.
Too $hort
Debut: 1983
Perhaps more than any other artist on this list, Oakland legend Too $hort’s name has become synonymous with pimpin’ on wax. As a true pioneer of Bay Area independent hip-hop, Too $hort’s bass heavy, trunk-rattling production and sexually explicit story raps served to make him a genuine star within the industry.
Short Dog’s memorably dirty rhymes never failed to skew humorously scatological or to paint him as anything less than the consummate mack. Classic songs such as “Freaky Tales,” “Blowjob Betty” and “Life Is… Too $hort” highlight gift for comic narrative in the tradition of raunchy black comedians like Rudy Ray Moore and Redd Foxx.
In a career that scanned over 30 years, 20 solo albums and countless classic cuts, Too $hort is one of the most prodigiously productive pimps ever.
Luther Campbell & 2 Live Crew
Debut: 1984
No title of a classic rap album serves as more of a group mission statement nor more as a frank admission of the group’s nature as 2 Live Crew’s As Nasty As They Wanna Be. The booty-obsessed Miami collective fronted by venerable horn dog, Miami mogul Luther Campbell A.K.A. Uncle Luke, were a group that had exactly three things on their mind: girls, girls, and more girls. With lyrics as dirty as their famously lewd stage shows that often included graphic sexual acts performed on stage by eager female fans on the band, 2 Live Crew was a magnet for controversy in their 1980s heyday.
In addition to their role as the progenitors of raunchy Miami bass music, 2 Live Crew became unlikely free speech martyrs when their famously dirty act would be famously outlawed for sale in the state of Florida. After the group was arrested on obscenity charges after performing in concert in Broward County in 1990, the group would eventually win an acquittal in U.S. District Court clearing the way for R-Rated rap music to be sold freely across the United States.
For their role in the struggle for free speech, 2 Live Crew has become one of the most unexpectedly important acts in American musical history.
Kool Keith
Debut: 1985
Don’t let Troy Ave tell you any different: weirdos can be pimps, too. You only have to watch Bronx intergalactic pimp screwball Kool Keith to understand the charismatic appeal of a good nutcase.
The chameleonic Keith has been spitting game and macking on a inter-dimensional journey through time and space since his debut with the seminal classic rap collective Ultramagnetic MCs 30 years ago. Known for his series of wildly divergent conceptual characters, from BX B-boy to Black Elvis impersonator, Kool Keith’s pimping magnum opus might be his 1997 “pornocore” concept album, Sex Style, in which Keith graphically rhymes about his sexual adventures from pimp to pervert. A true original in rap, Kool Keith keeps the game defiantly freaky with his constantly evolving funk.
Geto Boys (Scarface, Willie D, & Bushwick Bill)
Debut: 1986
Despite blowing up by depicting the graphic violent crime that occurred in he 3rd Ward of their native Houston, the Geto Boys knew a thing or two about the pimp game. Each member of the original lineup of the legendary Texas trio spent a significant amount of time rapping about the life of a pimp on record. When their collective minds weren't playing tricks on them, Scarface, Willie D, and Bushwick Bill were often off having elaborate sexual adventures with skeezers, skanks, and other scandalous women in the stories of their music.
Perhaps more so than his other two partners, the diminutive rap demon Bushwick Bill would push things a little further in the realm of outrageous sex; most notably on his classic 1991 solo track, “The Other Level” in which he humorously depicts a hot tub threesome between Bill and two eager women.
Big Daddy Kane
Debut: 1987
Draped in truck jewelry, boasting a smooth, buttery flow, and featuring a deadly poetic rhyme style, Brooklyn’s Big Daddy Kane would define what it was to be a certified player in 1980s hip-hop music. A deadly combination of vicious battle rhymes and leading man good looks made Kane equally popular with men and women of the era. The release of classic albums, such as 1989’s It’s A Big Daddy Thing and his 1988 debut Long Live The Kane, would establish Kane as the definitive player pimp prototype for future generations of Brooklyn emcees like the Notorious B.I.G. and Jay Z to emulate. As a template of effortless cool and debonair charm, Big Daddy Kane remains as raw as he did when he first stepped in the door.
Mac Dre
Debut: 1989
It’s easy to understand why they love Mac Dre in the Bay. As something approaching a regional folk hero to hyphy fanatics, Andre Hicks was pimp rap royalty to an area not exactly short on aspiring brothel-keepers. Dre’s legendary braggadocio and boastful rhymes captured an every man swagger that made him deeply relatable to fans on the West Coast. While unable to capture significant mainstream hip-hop fame, Dre’s truly independent hustle spawned a sprawling, massive discography that includes five unbelievable Best Of Mac Dre compilations filled with tunes dedicated to cars, hyphy culture, and the pimp life.
Tragically, Mac Dre would find his life cut short in November 2004 after being targeted by a drive-by shooting on an Kansas City interstate highway while on tour. His spirit and impact remain undeniable as Mac Dre remains an hero within Bay Are rap.
DJ Quik
Debut: 1990
When it comes to smooth hustler funk, Quik has always been the name. For nearly a quarter century, the man born David Blake’s reputation as a pioneer of slow-rolling, Compton street funk is unimpeachable and has served to fashion DJ Quik as one of the City of Angel’s most beloved artists.
With an icy sneer and permed coif permanently flowing, Quik hardly gives you a moment when his shit is not on point. As a visionary producer, accomplished studio musician, and versatile rapper, there is an argument to be made that Quik is one of the true geniuses in hip-hop; after all, his hybrid form of groundbreaking Piru-meets-player style sounds as fresh today as it did in 1991.
From his platinum-selling debut, Quik Is the Name, to his undeniably stunning contemporary LP, The Midnight Life, DJ Quik keeps it way too funky for one girl to handle.
Poison Clan
Debut: 1990
It takes a certain sense of total social irresponsibly to impress the great Uncle Luke himself, but that is what happened when the controversy-prone Luke Records honcho signed the Miami-based Poison Clan to his label in the early 1990s. Fronted by Sunshine State native JT Money, Poison Clan shared 2 Live Crew’s penchant for disrespecting women and booty-bumping bass beats. After releasing the group’s 1990 debut album, 2 Low Life Muthas, Poison Clan soon grew a reputation as one of the dirtiest, least-likely-to-win-an-award-for-feminism rap groups in hip-hop history. Songs like “Shake Whatcha Mama Gave Ya” might have been brimming with a wanton ignorance but were nevertheless devilishly infectious when ringing out on a dance floor.
8Ball & MJG
Debut: 1991
The city of Memphis, Tenn., has a rather infamous reputation for being something approaching a haven for illegal prostitution in America. Thus, it makes a certain amount of sense that two of Memphis’ most celebrated underground rappers, 8Ball & MJG, would be known as much for their lyrical breakdowns of the pimp game as they are for the sinister funk of their music.
With street-savvy rhymes and G-Funk-meets-Dirty-South production, 8Ball & MJG’s status as heroes of Memphis pimp rap has been established since their breakthrough album, Comin' Out Hard, in 1993. The duo has spawned classic odes to the game such as the Billboard-charting “Space Age Pimpin',” “9 Little Millimeta Boys,” and “Stay Fly” with Three 6 Mafia and Young Buck.
The pair have spent the last 20 years cataloging the intricacies of their brand of “pimping,” which was less about selling sex and more about achieving an excellence in their craft.
Three 6 Mafia
Debut: 1991
You’d be hard pressed to find a more unlikely rogue’s gallery of musicians to be the proud owner of an Academy Award than Three 6 Mafia. When you consider that race for the Academy’s Best Song is usually claimed by song-singing anthropomorphic woodland creatures and/or Randy Newman, the odds are certifiably loony that Three 6 would take a golden statue home for a song about a damn pimp; but that’s exactly what that group did when they won an Oscar in 2006 for their song “It’s Hard Out Here for a Pimp.”
Before they were Oscar winners, though, Three 6 Mafia started as a group of ostensibly devil-worshipping, Memphis lean sippers in the early 1990s. The group specialized in sordid tales of strip clubs, purple drank, and spinning rims on classic songs such as “Sippin’ on Some Syrup,” “Tear Da Club Up,” “Who Run It,” and “Stay Fly.” While the group has undergone more lineup changes than a hockey team over their long career, frontmen DJ Paul and Juicy J have always managed to keep the Three 6 Mafia brand relevant in rap’s ever-changing climate.
Snoop Dogg
Debut: 1992
There is hardly a sentient being in the known universe who does not recognize his face nor the melodic smoothness of his voice. Whether you know him as Snoop Doggy Dogg, Snoop Dogg, Snoop Lion, or just plain ol’ Snoop, Calvin Broadus is one of the most recognizable rappers in hip-hop history.
From a show-stealing debut as Dr. Dre’s co-conspirator on the Good Doctor’s 1992 mega-classic The Chronic, Snoop has continually defined his persona as the ultimate player-cum-gangster. Snoop was a pimp without trying overtly to be a pimp. Snoop’s definitive masterpiece, Doggystyle, was filled with the type of iconic songs like “Gin & Juice,” “Ain’t No Fun (If The Homies Can’t Have None),” and “Doggy Dogg World” that felt plucked from the soundtrack of a 1970s blaxploitation film. Snoop’s signature flow and laid-back stoner attitude gave him an ethereal cool that was unmatched during his prime.
UGK
Debut: 1992
Hailing from the small coastal town of Port Arthur, Texas, UGK were unapologetically trill and didn’t give a damn what you thought about it. Bun B and his partner Pimp C perfected a brand of blues/country rap tunes that celebrated the outlaw life of candy-painted cars, cocaine kilos, and a life spent pimping.
While Bun B was the regal and imposing straight man of the group, the late Pimp C brought an unhinged menace that was simply relentlessly entertaining. Not only was the man born Chad Butler the group’s undisputed musical guru, he came to be remembered by the outlandishness of both his fur-draped fashion and boastful, over-the-top rhymes. Tragically, Pimp C was taken from the Earth far too soon after a promethazine and codeine overdose claimed his life in December 2007. Nevertheless, Pimp and Bun were revolutionary during their time together, and won't be soon forgotten.
Dru Down
Debut: 1993
It takes a certain unshakeable confidence to sport a jheri curl. After all, the (hair)line is thin between being a confirmed mack and Eriq La Salle in Coming to America. Luckily, Oakland rapper Dru Down has the proper self-assurance to let his hair juices drip honed from years as one of the West Coast’s most notorious purveyors of pimp rap. Since his iconic 1994 breakthrough hit, “Pimp of the Year,” Dru Down has been breaking down the various intricacies of life as Bay Area player to glorious effect.
Devin the Dude
Debut: 1994
With a self-effacing personality and penchant for placing himself as the G.O.A.T. of his own stories, Houston oddball rap crooner Devin the Dude is in many ways the anti-pimp. However, Devin the Dude’s buttery smooth vocals and massive charm serves to make him as powerfully irresistible to women as any other man on this list. Debuting with the Rap-A-Lot affiliated Odd Squad in the mid-1990s, Devin the Dude eventually went solo and a built a career filled with country pimp rap tunes about weed, slow-rolling Cadillacs, and loose women.
On underground classics like Just Tryin’ Ta’ Live, To tha Extreme, and Waitin’ to Inhale, the Dude remains your friendly neighborhood mack.
Do or Die
Debut: 1996
Chicago rap group Do or Die brought a certified Midwestern swang to their own highly original brand of Windy City pimpology. Starting with their seminal single, “Po Pimp,” group members Belo Zero, N.A.R.D., and AK went from local sensations to national hit makers. The harmonious deliveries and Midwest traditional speed rapping featured on “Po Pimp” garnered the group a chart-topping hit that peaked at No. 22 on the Billboard 200 in the summer of 1996.
After capturing the attention of hip-hop giant Rap-A-Lot Records, Do or Die capitalized on their newfound success with release of their debut album, Picture This. The album continued with themes of high-life living on songs like “Paper Chase,” “Money Flow,” and “Playa Like Me & You.” While Do or Die are often remembered as something approaching one-hit wonders, the group’s impact in the Chicago rap scene makes them Midwest icons in the game.
Suga Free
Debut: 1997
Suga Free’s entire lyrical style sounds like game. As a longtime affiliate of fellow Cali legend DJ Quik, the Oakland-born Compton rapper was renowned for extraordinary tales of the lavish pimp life told with a signature blend of humor, ignorance, and genuine wit. His 1997 underground classic, Street Gospel, was a true pimp odyssey that highlighted a mastery of craft. Free’s supple, suppressive-fire flow displayed on the album was pure rhythmic genius, not only winning him the admiration of both fans and industry titans alike but showing that he possessed the natural gift of gab, able to talk the pants off a department store mannequin.
If you deny Suga Free’s place as a pimp rap legend, then the man has only one question to ask you: “Why you bullshitting?”
Roc Marciano
Debut: 1999
Over a long, lonely decade in an unforgiving rap industry, Hempstead-born MC Roc Marciano kept his nose firmly to the grindstone as he perfected the craft of his razor-sharp rhymes. After debuting as a member of Busta Rhymes’ Flipmode Squad in the late 1990s, it would take until 2010 with the breakthrough success of Roc Marci’s classic underground debut, Marcberg, to become finally acknowledged as one of rap’s fiercest lyricists.
Marciano’s musical style is a bit of a hybrid. While he remains a bone-breaking hardcore rapper in the tradition of Mobb Deep, Marciano’s ability to switch lanes and become a Godbody pimp is one of his signature features. On his acclaimed 2013 mixtape, The Pimpire Strikes Back, Marciano showcases a narrative lyricism devoted to a vicious pimp game that is as marvelous as anybody.
Action Bronson
Debut: 2010
While at first glance with his unkempt beard and massive heft, Queens rapper Action Bronson and the word “pimp” don’t seem to be a natural fit. On the low, however, Bam Bam Bronsolino has managed to keep the legacy of pimp rap alive in his music since coming onto the scene in 2010. Bronson’s music has enjoyed a personal fascination with all things pimp-related. He frequently makes allusions to his personal love of prostitutes on a plethora of tracks; most notably on his 2012 mixtape cut “Hookers at the Point."
On the track, Bronson manages to craft a song looking at prostitution from all angles, writing verses from the perspective of the pimp, the john, and the girl in question. Beyond his personal enthusiasm for pimping, the man’s overly outsized personality and a stated love for fine cuisine make it easy to imagine the lordly purveyors of pleasure would come to appreciate all things Action Bronson.
100s
Debut: 2012
A mere glimpse at 100s and you realize the smooth Berkeley native is as much a vintage throwback to the pinnacle of the pimp game’s 1970s prime as anybody born in the 1990s could possibly be. As a certified young mack with the perm and attitude to match, 100s is defiantly making classic neo-pimp rap in the modern era. Since releasing his acclaimed debut mixtape, Ice Cold Perm, in 2012, the upstart Bay Area MC has achieved significant critical success and has taken his icy cold super player act to indie label powerhouse Fool’s Gold. 100s is proving that while the game might be in decline, pimping ain’t dead yet.