It is hard for any successful person - especially in the entertainment world - to have a little success and make some friendships without making a few enemies along the way. No one in the comedy world knows that truth better than Dave Chappelle. He had a rise and fall as a comedian without necessarily having a fall. Unlike most "rise and fall" stories, he didn't waste his resources or fall to his vices, but his 15 minutes ended simply because he walked away from a heap of money and a worldwide syndicated Comedy Central show. People very much thought we had seen the last of him on television and perhaps stand up all together, but in the last five years, he's come back bigger than he's ever been. How?
Well, for starters, besides his successful Netflix specials, he has a wealthy assortment of friends by his side who serve as a support system and vital career connection. He has made just as many friends as he's made enemies. Who are these friends, you may wonder? And who are these enemies who pray to see Chappelle's downfall? Let's take a gander below and find out.
13 Friend: Kevin Hart
Kevin Hart is undoubtedly the most popular comedian of his era today, but no matter how famous he gets, he also gives props to the top dogs in comedy who came before him, like Dave Chappelle. As recently as his last interview with Joe Rogan on YouTube, Hart hailed Chappelle as "the GOAT." That mutual respect has spurned into a genuine friendship between the two.
12 Foe: R. Kelly
One of the most popular skits from Chappelle's Show was the skit of the titled comedian spoofing R. Kelly and his alleged fetish for urinating on his partners. According to Chappelle during a stand up routine of his, he found himself bum rushed by some "goons" acting on behalf of Kelly, who wanted to let Chappelle know the singer did not find his sketch to be funny.
11 Friend: Kanye West
When Kanye West first started to break onto the music scene as a rapper, Chappelle gave him his first big break by letting him perform not only on his Comedy Central show, but in his Block Party movie. To this day, him and West are still friends, although Chappelle continues to be vocal about not agreeing with some of his friend's political stances.
10 Foe: Jussie Smollett
Jussie Smollett was at the center of controversy when he was embroiled in a hate filled attack fueled by racism and homophobia, only to then be accused of making the whole thing up. This entire incident made for ample material in Chappelle's stand up for his Sticks and Stones special, where he comically eviscerated Smollett's predicament.
9 Friend: Pete Davidson
Pete Davidson has proven in the past how well he knows his way around Hollywood circles and even managed to weasel his way into Dave Chappelle's friend circle. After a few startling messages on social media right after breaking up with Ariana Grande, he was invited by the comedian to Chappelle's cabin in Ohio for Christmas to feel better.
8 Foes: Key and Peele
Key and Peele, helped by its title stars, proved to be Comedy Central's biggest hit since Chappelle's Show. However, not only is Dave not a fan, but he told CBS This Morning that he felt he deserved some credit because Keegan-Michael Key and Jordan Peele used the very comedy sketch format that Dave "fought hard" to make the air waves.
7 Friend: Neal Brennan
Neal Brennan is a key collaborator who frequently works with Dave Chappelle; the two co-wrote both Chappelle's Show and the movie Half Baked. Their friendship briefly became strained when Chappelle left production on the show and ultimately led to its cancellation, but they patched things up and continue to be the best of friends today.
6 Foe: Azealia Banks
In a more recent revelation (if it is even true), Azealia Banks claimed during an Instagram Live session that she had an affair with Dave Chappelle once upon a time ago. Keep in mind that Chappelle is married and has been since 2001. Naturally, Chappelle has yet to respond, but keep your eyes peeled for a response whenever he drops his next stand up special.
5 Friend: Chris Rock
Many comedy enthusiasts have had their debates on who is funnier: Dave Chappelle or Chris Rock. If Rock had to choose, he'd pick Chappelle any day of the week. When his buddy made his triumphant return to the comedy stand up world in 2017, Chris Rock went on record to say that Chappelle had the best comedy special that anyone had put out since 2014. Shows how much respect one comedy legend has for another.
4 Foe: Daniel Caesar
While backstage at a John Mayer show on his Instagram Live, Dave Chappelle insinuated that one of the performers in attendance was "very gay." The performer in question - Daniel Caesar, who isn't gay - just so happened to walk into the room at exactly that moment. An argument between the R&B singer and the comedian ensued.
