The Hip-Hop Sketch Comedy Pioneers Who Paved The Way For Open Mike Eagle And Kyle

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In recent years, hip-hop music has come to dominate the airwaves and streaming, but there’s one expected place it’s beginning to make its presence known: On television — specifically, in sketch comedy shows like Open Mike Eagle and Baron Vaughn’s The New Negroes and Kyle’s upcoming Sugar & Toys. Open Mike’s musical riffs on sensitive subjects through rap lyrics have struck comedy gold, with “Woke As Me,” “Extra Consent,” and “Unfiltered” tackling tough topics with wry wit and ticklish turns of phrase, while Kyle’s injection of goofy rap tropes already has both hip-hop heads and comedy fans ready to binge his show when it drops.

Rap has always popped up on TV in ways both mundane and unexpected. First there were sitcoms like The Fresh Prince Of Bel-Air and MTV’s early 2000s televised rap battles capitalizing on the popularity of BET’s “Freestyle Fridays” segment of 106 & Park. And of late, with cartoons like Vince Staples and DRAM’s roles on Cartoon Network’s Lazorwulf, hip-hop has been infiltrating sketch comedy more and more, to an extent not seen since the 2000s. Now, Saturday Night Live can mine hip-hop for some hilarious vignettes like the “Friendos” bit that rankled its parodic targets and the infamous Lonely Island sketches that launched a legit music career.

But while the recent relative explosion of rap sketch comedy may coincide with an overall increased interest in rappers’ personalities outside their hits — see The Rap Game, Love & Hip-Hop, or The Family Hustle — it actually has deeper roots in the form that precedes even early rap TV breakouts like Wild’n Out and Ego Trip’s The (White) Rapper Show. While there are plenty of shows that riff on rappers and plenty of rap skits that went down in history for their legendary laughs, there were a few shows that made the rhymes the center of attention, using them to drive both the stories and the chuckles that followed. These are the shows that first combined the narrative potential and street-smart attitude of hip-hop with the comedic potential of sketch shows like SNL, paving the way for Kyle, Open Mike Eagle, and more to flourish with rap-centric hilarity.

All That

Although technically the 21-and-under cast of this mid-90s Nickelodeon staple left most of the actual rapping to the shows inexplicably age-inappropriate musical guests (seriously, did anyone check a lyrics sheet before booking Craig Mack for “Flava In Ya Ear” or Nas to perform “Street Dreams,” let alone the baby-making hits that permeated the majority of the show’s musical guest list?), All That did introduce to television some of the flair of hip-hop, with characters adopting the culture’s dress and slang long before many other shows would eventually do the same.

But there’s one sketch where All That stood out in bringing hip-hop to sketch comedy stage: “Baggin’ Saggin’ Barry.” Even his name is damn near a rap, but what made Kenan Thompson’s beloved recurring role so groundbreaking is that it was maybe the first time sagging clothes or the practice of “bagging” — now known as roasting in modern parlance — was portrayed on TV. There was even one episode that pitted Barry against a rival, Baggin’ Saggin’ Mary, in a rap battle of sorts. If All That ain’t hip-hop, nothing is.

Chappelle Show

Perhaps no other straightforward sketch show mined hip-hop tropes for comedic material as skillfully as Dave Chappelle, who was friends with many of the rappers who appeared on the show, including the Wu-Tang Clan and Mos Def. He loved to work in some of the goofiest rapper habits like his fictional Fisticuffs’ insistence on turning his headphones up or the outrageous items they’d show off on MTV’s Cribs. Not to mention, his take on MTV’s reality show centering Da Band is legend.