Many consider Chappelle’s show to be one of the greatest sketch comedy shows of all time. It approached important issues like race, contemporary politics, and cultural issues with a blend of comedic genius that only Dave Chappelle could conjure – and audiences couldn’t get enough of what he serving up.
The show rose to popularity in its second season and eventually presented Dave with the opportunity to seize a massive contract – which he did – but subsequently regretted, resulting in his notorious retreat from the spotlight. The show that gave Dave his skyrocketing rise to fame had been his undoing and soon enough it faced the chopping block of cancellation.
Once again a television show with a massive following bit the dust much too soon. Fans were left scratching their heads trying to figure out what happened – but in order to solve that mystery, you’d have to turn to Dave himself.
According to Chappelle, his sudden exposure to the limelight – with all the pressures and expectations that fame can bring – was disastrous to his spiritual and mental health.
It’s hard to believe that Chappelle’s Show premiered almost 2 decades ago. Let’s take a little look back at the show and some little known facts related to it. Stick around to find out why Dave regrets ever being apart of it.
Facts Verse Presents: Dave Chappelle Says His Show Ruined His Life
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Hugh Hefner Inadvertently Inspired Chappelle To Create His Show
Late one night many years ago, Dave was watching a television special that attempted to recreate what parties at the Playboy Mansion looked like. The host went around and interviewed his guests, which included musicians and comedians. Of course at the real mansion, Hef would have these performers give him a show, and then there was his entourage of helpers, assistants, and yes-men, and how could we forget the Playboy bunnies?
Chappelle chatted with James Lipton on Inside The Actors Studio a few years about this experience and how it was weirdly inspiring to him. Dave recalls calling up Neal Brennan who he co-wrote Half Baked with back in the late 90s, to bounce ideas off of.
He got the idea to do a variety show of sorts, but he wanted to make it more personal. Eventually, this discussion led to the formation of what became Chappelle’s Show.
HBO Didn’t Want Anything To Do With The Show
Brennan and Chappelle first went to HBO to pitch their idea.
To put it lightly, they were less than enthusiastic about the concept and passed.
Brennan told Free Press Houston that “they looked at us like we lepers.”
Sometimes you got to get the no’s out of the way to make room for the yeses.
Chappelle And Brennan Learned How To Script The Show From A Book About SNL
Having no clue how to write a sketch comedy show, the two sat down with a copy of James Andrew Miller and Tom Shales’s book Live From New York: The Complete, Uncensored History of Saturday Night Live as Told by its Stars.
The two drew heavily from the volume when writing sketches for the first season and while compiling footage for the pilot. Brennan described the book as especially informative and helpful to their creative process.
Donnell Rawlings Improved His Player Hater’s Ball Character
In an interview with King Magazine, Rowlings divulged that his Player Hater’s Ball character really wasn’t even a thing until the last minute when he came up with it on the fly.
It was minutes to show-time and he still had nothing, so he went to hair and make-up and asked for a Jheri-curl wig, then he went over to the prop department and asked for a bottle of Moet champagne with an activator on it so he could douse his hair periodically. They didn’t have that so he just grabbed an aerosol can instead.
He didn’t have a name either so Neal Brennan just told him to make something up. That’s when he walked up to a mirror and said “Man, I feel beautiful.’ and that was the moment ‘Beautiful’ came to be.
Wayne Brady Hated What Negrodamus Said About Him
Brady was a huge fan of the show and went out of his way to make sure he never missed an episode but when he saw Paul Mooney playing the character “Negrodamus” say that ‘white people love Wayne Brady,….because [he] makes Bryant Gumbel look like Malcolm X”, he was pretty offended.
So at the NAACP Image Awards, Brady sought out crew members of the show and bought them all drinks. He proceeded to explain to them how he resented the comments. Dave called him up the next day and invited him on the show which ended up giving birth to one of the funnier moments in the series when Wayne Brady showed off his dark side.
Chappelle Hadn’t Planned on Playing Samuel L. Jackson in the Samuel Jackson Beer Ad Sketch
Sometimes Dave and Neal would cast people and they wouldn’t capture the magic of what they were looking for in a role. In their imaginations, they had this vision of how a gag or a character was supposed to be but unfortunately, people aren’t mind readers.
Oftentimes, when they really had an idea that they thought might be difficult to execute, this would mean Dave would jump in and do it himself to ensure that his vision was accurately depicted.
The Dude That Did The Robot Was The Set Designer
Karl Lake, the show’s set designer first appeared on camera when they were doing an And-1 sketch. Brennan thought it would be hilarious if everyone just started ‘bugging out’, as he put it.
To further add absurdity to the bug-out session, Karl Lake impromptu started doing the robot, and it was so outlandish that they kept doing it until it became a recurring thing. At that point, they just stuck with it. No sense in getting rid of a good thing.
The Racial Draft Sketch Was Filmed Across From Jay-Z’s Last Concert (at the time at least)
RZA from the Wu-Tang Clan (who apparently were drafted as full-fledge Asians in the sketch) suddenly disappeared for an entire hour and delayed the production of the show. He explained when he got back that he had gone over to Madison Square Garden to catch some of the concert.
Bobby Brown Got Arrested Before He Could Do The STD Puppet Scene
Bobby was no stranger to being on the wrong side of the legal system. He would be arrested several times, infamously assaulting his ex-wife, singer Whitney Houston.
Scrambling to find a replacement for the Kneehigh Park Sketch’s pivotal character, producers called up Andre 3000 from Outkast and Pharrell. Both declined, so they kept on with their search. Q-Tip however agreed to do the sketch and then Snoop Dogg who was already signed on to do a ‘Weed Olympics’ sketch that later got cut got involved as well.
Lil Jon Rose To Popularity Partly Because of Chappelle’s Show
LilJon credits much of his meteoric rise into stardom to Dave and his show. He noted that he was suddenly thrust into popular culture and not just in the urban community but with white culture as well.
He described to MTV how he would be out at the grocery store or at the airport and random white ladies would come up to him and ask him if he was Lil Jon.
The Whuuuut? Yeaaaaah and Okaaay! Catchphrases became something of a cultural sensation at the time. It got so big that when Chappelle noticed audience members at the MTV VMA’s shouting the phrases at Lil Jon when he was on stage, he felt the need to personally apologize to him.
Charlie Murphy Came Up With The Rick James Sketch
Eddie Murphy’s older brother Charlie were sitting at a table and enjoying a bite to eat one day while taking a break in between shots while doing the ‘Calvin’s Got a Job’ bit. Murphy recalled the times when he and Rick James used to hang out and he got the whole table full of crew belly laughing. Chappelle then suggested that they should reenact those moments for the show and the rest is history. Unfortunately, Charlie Murphy passed away from leukemia in 2017.
Eddie Murphy thought the sketch was absolute comedic gold. When his brother first showed him the video, he sat and watched it in silence. When it finished, he called it ‘genius’ and asked to play it again.
Chappelle Met Rick James When He Was 19
Dave was in LA in 1992 filming Robin Hood: Men in Tights. He was only 19 but he ended up hanging out at the hotel bar with Rick a few times.
Unfortunately, the sketch had some unintended effects on a politician by the name of Rick James who was running for city council in Hattiesburg, Mississippi.
His campaign signs were being routinely defaced with the popular phrase from the show being added. Many of the signs got stolen as well. James, the politician reported seeing his signs as far away as 100 miles from his town.
Prince Got Even
Prince confirmed in an interview a story about him beating Charlie Murphy at basketball, but he wanted to make it known that it wasn’t because he was any good at the sport, rather he said that Charlie Murphy was particularly bad out there on the court.
Then in 2013, Prince dropped a single called ‘Breakfast Can Wait”, where he used a picture of Chappelle dressed up as him for the cover. That left Dave option-less because he wasn’t going to sue him for using a picture of himself dressed up as Prince.
Chappelle Grew Tired Of His Fans And Fame
In 2004, he got really frustrated with the crowd at one of his stand-up shows and called them stupid for yelling “I’m Rick James B****” at him while he was trying to do his routine. He told that same audience that the show was ruining his life.
Soon after, he straight-up walked away from his massive $50 million contract and escaped to Africa.
Chappelle went on Oprah in 2006 and told her that he felt like the people around him were manipulating him because he was generating money. People had a vested interest in controlling him because he was also lining their pockets. He had grown tired of the fakeness that fame brings.
He wanted to reconfigure his Comedy Central contract – namely, he wanted to give away most of his money to people in need. Instead of taking him up on the contractual changes, they aired a very abbreviated third season and bid him farewell.
Fame is probably one of the hardest things to go through when it’s not something that you want or expect. Some People are cut out for it and others just want to have low-key humble lives.
How do you think you would handle fame if you were suddenly thrown into the limelight? Would you get overwhelmed and dip out as Dave Chappelle did or would you embrace it and ride it like a wave? Let us know what you think in the comments section.
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