[Ed Note: This was originally published on August, 23, 2013]

Dave Chapelle is making his comeback this summer with nine scheduled shows at New York City’s famed Radio City Music Hall. The shows will feature a stand-up set but also a full orchestra and co-headlining musical guests like The Roots, Busta Rhymes, DJ Premier, Erykah Bad, Janelle Monae and Nas.

Despite not having aired an original episode in a long while, few shows are universally beloved as Chappelle's Show. This is particularly great because few shows have shown as much love towards hip-hop than Dave Chapelle's satirical masterpiece on the intersection of race, pop culture and American comedy. Perhaps more than any other comedian in history, Dave Chappelle has been hip-hop's comedian. Versed in the culture and minutiae of a true hip-hop fan, Chappelle's Show is coded in the language and culture of rap music.

Over the too brief 28 episodes of the series, hip-hop played a vital part in the show's appeal. Whether, it was the numerous guest performances by rappers on the show or appearances by rappers and artists in the show's many classic sketches, hip-hop was present in one of the 2000's shining examples of American comedy.

XXL brings to you a collection of the many the greatest guest appearances by hip-hop over the years on the show. These are the moments that made Chappelle's Show, one of the defining shows in hip-hop history.

"Lil Jon" Meets Lil Jon

One of Dave's classic impressions during the course of the series was his take on Lil Jon. Despite reveling in the Jon's trademark exuberant calls of "Yeah!", "What?!," and "Ok!", Dave would allow Jon to show previous moments of erudite intelligence as he interacted in various, normal situations like booking a plane or seeing a doctor.  It made for an impression that made Lil Jon more than a ridiculous buffoon as his moments of lucid normality seemingly called to Lil Jon's background as an accomplished college graduate.

One of the more inspired sketches was when Chappelle's "Lil Jon" received a phone call from the actual, real life Lil Jon in a sketch. While the sketch primarily revolves around the two Lil Jons happily yelping their catchphrases at each other in increasingly absurd fashion, buried within the ridiculous non-sequiturs about numbed hand masturbation and Oprah, there is an actual pathos as "Lil Jon" complains to Lil Jon that nobody understands them. It's inspired comedy and the real Lil Jon shows remarkable comic delivery.

Dave Chappelle is Big Boi's Annoying Friend

We all have that annoying friend that we dread talking to when we pick up the phone. Inevitably, you will be invited to some event that you have no desire of attending but will feel guilted into going because either you can't come up with a reasonable enough excuse or because you don't want to hurt this person's feelings.

In this sketch, Dave is Big Boi's annoying friend that he would like to avoid. After Chappelle had lost his show to his hated rival, Wayne Brady, Dave finds himself with too much free time to spare and calls to see if Big Boi wants to come out and hang. Big Boi registers that moment of annoyed disgust when he realizes that Chappelle is on the other line and offers a ridiculous excuse to avoid hanging out: Tennis with Don Cornelius on the Moon.

Later in the sketch, sort-of rapper, Nick Cannon, shows up to taunt Dave about his status as Chappelle's son favorite comedian.

Wu-Tang Clan Are Drafted By The Asians

In one of the signature sketches of the show, Chappelle imagines a world where the races could adequately draft racially-ambiguous celebrities on their team to fit their idea of their culture. Mos Def shows up in the sketch as an Afro'd slickster representative of the Black Delegation to draft Tiger Woods (Chappelle) to the team. This leaves the Asian delegation suitably pissed that they could not draft Tiger Woods first.

In perhaps one of the more memorable jokes from the sketch is when it's the Asian delegation hatches their revenge. In a steal, they draft the entire Wu-Tang Clan and up pops The RZA and The GZA to remind the crowd to "diversify your bonds."

Konichiwa, bitches!

Dave Mocks The Ying Ying Twins

In a short sketch mocking the Ying Yang Twins buffoonish appearance on the MTV's Cribs, Chappelle dresses like a blackfaced bellhop straight out of  an Amos N Andy routine to offer commentary MST3K-style to Ying Yang's howling and monkey statue collection. This sketch is ruthless in its ability to cut directly to the point. To be fair to D-Roc and Kaine, that is a pretty cool monkey statute, though.


?uestlove Play Drums In Barbershop With John Mayer

Although the show was mostly devoid of hackneyed "White People Act Like This! Black People Act Like This!" comparison comedy, Chappelle made an exception to discover the actual idiosyncrasies that real-life people would have if you'd play them electric guitar, drums and Latin Piano in a series of inappropriate places.

Roots drummer ?uestlove and guitarist John Mayer joins Dave as they run an experiment to find out the appropriate reactions of people in Harlem barbershop. This sketch ends with Dave toasting in Spanish over a microphone as the Latinos salsa dance in the barbershop.

Ice-T Hosts The Player Hater's Ball

For aspiring trick-ass marks and mark-ass tricks, the "Player Hater's Ball" is one of the most imminently quotable sketches in the history of the show. It introduced us to some of the show's most enduring and hilarious characters like Silky Johnson, Buc Nasty, Beautiful and Mr. Roboto while delivering some of the most ruthlessly hilarious one-liners around.

Ice-T shows up in the sketch to host the annual ball - loosely based on the real-life Player's Ball for pimps in Chicago - and to air his grievances against everybody around him. Meanhile Star of Star & Buc Wild radio show shows up to narrate and offer his opinions of the festivities.

"Dylan. Dylan. Dylan. Dylan. Dylan."

One of the innovations of the show was Dave's ability to skewer the conventions of the burgeoning reality television show phenomenon in it's early infancy. Whether it was mocking the manufactured conflict on "The Mad Real World" or the asininity of a show like "Wife Swap," Chappelle's Show was cutting edge when it came to mocking pop culture.

Perhaps, Chapelle's greatest show parody was his destruction of Diddy's Making The Band. Chappelle's inspired take on Diddy's tyrannical lunacy is one of the most memorable aspects of the sketch. Members of Da Band actually show up in the sketch to poke fun of the show but Diddy's increasingly ludicrous demands poke fun at the scripted conflict of reality shows.

Pure 100% Cambodian!

Wu-Tang Advices You To Diversify Your Bonds

In a series of hip-hop commercial parodies, Chappelle was able to prove how much he kept a finger on the pulse of hip-hop. Understanding the level (and at time's overreaching absurdity) of hip-hop entrepreneurialism that had grasped rap music during the early 2002s, Chappelle stuck a satirical jab at rap's obsession with commercialism.

"Wu-Tang Financial" takes the notion of a rap entrepreneur to the logical extreme. The RZA and The GZA show up again to offer financial advice to middle-aged white folks in a corporate setting. There is also extreme comedy in watching white geezers attempt to stiffly throw "the W" into the sky.

Redman Potty Fresh

Although, Chappelle's Show was primarily known for stinging racial comedy, sometimes the show devolved into toilet humor, too. In this sketch, that is quite literal as Redman offers solutions for toilet hygiene. Acting as a magical toilet cleaning fairy, Redman endorses his signature new product, Potty Fresh, to every stereotypical stay-at-home mom from your favorite soap commercial

Dame Dash Wants To Sell You Tampons

Sometimes, Chappelle's Show was brilliant satire. Sometimes, Chappelle's Show as Dame Dash selling Rashida Jones Roc-A-Fella-brand tampons. The brilliance of naming the tampons "Roc-A-Pads" has not been lost. Also, Dame Dash is a fool in this one.

It's the Roc!

Kneehigh Park

There is something ripe for parody in the squeaky clean world of children's television shows. MTV's short-lived but undeniably brilliant Wonder Showzen mastered the art of transforming kid's TV from something pure into something undeniably dark and scary.

Chappelle's take on children's show is wonderfully unhinged as anything as you will see on television. "Kneehigh Park," a horrifying hip-hop Sesame Street, is the world of educational television nightmares. Snoop voices an unfortunate puppet with a undiagnosed case of venereal disease. Meanwhile, Q-Tip shows up to sing a song about the dangers of puppet herpes. It's deranged. It's weird. It's Chappelle.

This is darkly hilarious stuff. There is also something strangely soothing in Q-Tip's singing voice that would suggest that he would have made a wonderful replacement for Mr. Rogers had Q-Tip been really into cardigans as a child. (He can borrow Common's!)

Musical Performances

Not since perhaps The Arsenio Hall Show (or if we are really keeping it real, Nickelodeon's All That) has a television show had so many memorable hip-hop performances as Chappelle's Show. It seemed as if each week, there was another incredible performance by a rap artist that would close out the show for the audience.

Whethe it was DMX's refusal to stop rapping (see above), an incredible Brooklyn Bridge-side performance of Kanye's "Two Words" or Snoop Dogg dueting with Tyrone Biggums to perform "Deep Cover," the show was laced with some of the most incredible performances in hip-hop history.


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