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.

However, one of his crowning achievements — a little underrated in comparison to his “True Hollywood Stories With Charlie Murphy” or the “Racial Draft” or the iconic Lil Jon sketch, perhaps — was the way he pulled off a pitch-perfect Tupac impression to send up the eerie way in which the late west coast superstar seemed to predict events way ahead of their times. It was the illest song he ever wrote — in ’94.

Freestyle Love Supreme

By now, playwright and rapper Lin-Manuel Miranda is practically a household name thanks to the ridiculous popularity of his historical rap musical Hamilton (that sounds like a halfway decent sketch premise right there, no?), but his roots in comedy and rap go back even further than that. In college, he formed a hip-hop improv troupe called Freestyle Love Supreme, playing off the similarities between improv stage acting and freestyled, “off-the-head” raps.

Eventually, the show was picked up by Pivot TV with a cast that included Christopher Jackson (who played George Washington in Hamilton‘s original Broadway run) and Utkarsh Ambudkar (who appeared in Blindspotting and put out a couple of albums). While it lacks the production value of a fully-fleshed out sketch show, the troupe uses suggestions from the audience to build out convincing scenarios — all while rhyming the story as it pops into their heads.

Key & Peele

The challenge with finding a Key & Peele sketch that perfectly encapsulates how thoroughly they wove hip-hop into the threads of their Comedy Central show is picking just one that gets the job done. From “MC Mom” to “Rap Battle Hype Man” to “East/West Bowl Rap,” Keegan-Michael Key and Jordan Peele integrated goofy rhymes into their punchlines and drew side-splitting gags from asking the question, “But what if we rapped it, though?”

The true winner, of course, is “Rap Album Confession,” which plays off rap’s own obsession with “keeping it real” and deftly predicts the modern prosecution practice of playing rappers’ records as evidence in cases against them — a practice that paid dividends in cases like those of Bobby Shmurda and Tekashi 69, where viral hits painted the picture of criminal activity a little too vividly.

Lyricist Lounge Show

Speaking of confessions, if any readers were wondering whether this whole feature idea was just an excuse to write about the criminally short-lived Lyricist Lounge Show, well, I plead the fifth. Based on the popular New York-based open mic series which spawned a pair of classic compilation albums and launched the careers of underground favorites like Yasiin Bey (formerly known as Mos Def), this series was truly the first show that used rhymes to tell the story.

Unfortunately, it was probably a little too underground for its MTV audience. Though it did feature appearances from big names like Snoop Dogg, Erykah Badu, and MC Lyte, its main cast consisted of Lyricist Lounge mainstays like Wordsworth, Thirstin Howl III, Tash, and a then-unknown Tracee Ellis Ross (in her first television role). Since the cast members were mostly rappers, there was probably more focus on the rhymes than the comedy, which both require different rhythms to effectively land. In the end, the show was probably just too far ahead of its time, but Open Mike Eagle’s current run of hilarious music videos do carry the torch.

Scratch & Burn

The cancelation of Lyricist Lounge Show didn’t completely deter MTV from the concept. The network tried again a few years later, this time apparently hoping that by swapping in a cast of white guys, the show would appeal more to their demographic. It didn’t work any better the second time around — in fact, the show got canceled after only five episodes aired. Still, it was fun while it lasted, with bits that upended the typical expectations of rap at the time.

These dudes weren’t cool, they weren’t ballers, they didn’t get the girl, and they weren’t tough in the slightest. What they did have was an unabashed willingness to make themselves the butts of the jokes — something plenty of “real” rappers wouldn’t go for, and a slightly better grasp of the setup-knockdown strategy that fuels usual comedy, taking more bars to set up their punchlines before the comedic twist.