The Game Is to Be Sold, Not to Be Told: A Look at Pimp Rap Through the Years

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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?”

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.