Dave Chappelle is undoubtedly one of the most celebrated living comedians. The stand-up comedian, actor, writer, and producer’s 28-year career has spanned massive successes, which also included his highly popular sketch comedy show “The Chappelle Show”, which ended up being a source of contention for Chappelle.
The Grammy award winner shocked the world when news hit that he would abruptly be leaving “The Chappelle Show” after it being such a huge hit for the network and viewers alike. The show’s third season was originally scheduled to premiere in February of 2005, but was then pushed back to May.
The show would ultimately be suspended indefinitely, and reports begun to arise that Chappelle retreated to South Africa where he would be seeking psychiatric help, a rumor that would later be denied by Chappelle himself. The legendary comedian insisted that his trip was not due to psychiatric or substance abuse issues, but rather a “spiritual retreat intended to keep his sense of reality outside the bubble of intense pressure and fame and to keep his humor fresh.”
Reasonings for the show’s initial delay were said to be due to Chappelle contracting the flu during filming, which he would later confirm would be untrue during an interview with Oprah, saying it was stress that caused him to leave. Comedy Central’s president Doug Herzog said on July 14th of that year that Chappelle was “welcome to return back any time”, and there were talks of negotiations upwards of $50 million for him to return and complete a third and fourth season.
In February of 2006, the Emmy Award-winning comedian appeared on the Oprah Winfrey Show, his first televised appearance since production ceased on season three of The Chappelle Show, and gave his explanation as to why he stopped, stating burnout, loss of creative control, and an uncomfortable work environment were among some of the reasons that he left the show.
One of the most notable sketches on the show, “Charlie Murphy’s True Hollywood Stories”, gave viewers an inside look of the late comedian’s encounters with certain celebrities, including Prince and Rick James. His stories of Prince included him and his crew losing a game of basketball to the “Purple Rain” superstar, to which Prince would later confirm to MTV to be a true story, saying “The whupping is true”.
The late artist’s estate, as well as Warner Records, announced on June 25 that they would be re-releasing his “Sign O’ The Times” album as a “Remastered”, “Deluxe” and “Super Deluxe” edition on September 25, 2020. Chappelle was given the honor to write the re-release liner notes and the comedian shared some retrospective moments he’s had with the legend. The two shared similarities as Prince also had issues with his then record label, Warner, pushing him in protest to write “Slave” on his face at a performance during the 90s.
“When I left Chappelle’s Show, not only was Prince the only person I could relate to, he was one of the few people who truly cared about what was happening in my life,” Chappelle states. “He was the only one I knew who had already done it […] The mere sight of Prince reminded me that I’m not the last sane man on earth, and I’m not crazy.”
Continuing on his reflection he adds, “he just told me, ‘whatever it is, you’re right.’ He helped me understand that it might not be over and that there might be another side to it […] and whether or not there is or isn’t, at least you’re free. Or, as he would say, ‘U gotta B free.’”