Dave Chappelle’s third season of his iconic Comedy Central show from 2006 is back in the spotlight, reigniting discussions about his decision to walk away from a $50 million contract at the peak of his career.
Saying Goodbye to His Show
Chappelle hosted “Saturday Night Live” for the fourth time on Jan. 18, where his opening monologue briefly reflected on his sudden exit from the show’s production and his decision to retreat to South Africa. In 2006 most people had no idea what had happened and were wondering where in the world was Chappelle. He had seemingly disappeared, leaving his family and the show behind. After some time he made it be known he was solo in South Africa.
Just days before Chappelle’s “SNL” appearance, his longtime friend and “Chappelle’s Show” co-star Donnell Rawlings opened up about the infamous breakdown in the Jan. 16 episode of Shannon Sharpe’s “Club Shay Shay” podcast, offering an insider’s perspective on the events that led to Chappelle’s infamous departure.
“Chappelle’s Show,” launched in 2003, was a pop culture phenomenon that stood out among skit shows. It averaged 3.1 million viewers and became the top-rated program in its time slot for men aged 18 to 34. The first season of “Chappelle’s Show” broke DVD sales records, selling approximately 3 million copies, according to Forbes.
The second season of the show did not disappoint fans, introducing “Charlie Murphy’s True Hollywood Stories” segments, including the Rick James sketch with the famous “I’m Rick James, b–!” The second season also sold about 3 million copies, with first week amassing 1.2 million copies.
Unfortunately, Chappelle struggled to adjust to his newfound fame, often having his own catchphrases thrown back at him during his stand-up routines. Additionally, although he had some creative control, he experienced internal conflict with the jokes that portrayed Black people for a predominantly white audience. Chappelle wanted the jokes to provoke laughter rather than reinforce stereotypes about the culture.
The third season was in production in 2004 when Chappelle walked out. As a result, the season remained incomplete, with only three episodes produced. These episodes, referred to as “The Lost Episodes,” include “Black Monsters,” “Black Howard Dean,” and “Stereotype Pixies,” the latter of which he considered socially irresponsible, according to Newsweek.
During the taping of a sketch about magical pixies that represented racial stereotypes, Chappelle played the Black pixie, complete with blackface, who encouraged Black people to act in stereotypical ways. Chappelle initially found the sketch funny, however, during filming, a white man viewing the sketch laughed excessively, and Chappelle found the laughter unsettling. It made him question whether the show had shifted from mocking stereotypes to reinforcing them.
“When he laughed, it made me uncomfortable,” Chappelle recalls, according to The Atlantic. “As a matter of fact, that was the last thing I shot before I told myself I gotta take f______ time out after this. Because my head almost exploded.”
He walked away from $50 million, which he wondered was even enough for what he was going through.
During the most recent interview with Rawlings, Rawlings recalled taping an episode where the three men — Chappelle, Charlie Murphy, and himself — played as 1960s monsters Frankenstein’s Monster, a werewolf, and a mummy. While Murphy and Rawlings enjoyed the skit, Chappelle was unimpressed behind the scenes.
“I played a mummy, he played a wolf, and Charlie played Frankenstein or whatever, right? And me and Charlie were just having fun on set. We were kicking it, kicking it. And I saw Dave — he was a werewolf — and he was just looking like. … and then he said, ‘I guess 50 million is not enough,'” Rawlings said.
“And I was looking at him like, ‘Who you talking to? $50 million not enough?’” Rawlings continued. “I take the zero, you could take three more of the zeros off, and I’m good with it. I didn’t know what was troubling him, but that was just … For somebody like me, still coming up, not used to having big money or anything, I was like, ‘I don’t even understand how anybody can say, ‘I guess $50 million is not enough.’ I didn’t understand that. And then he just disappeared, not communicating with me.”
While Rawlings may have been clueless as to what was irking Chappelle, Chappelle did later explain.
In a 2006 interview with Oprah Winfrey, he said, “I felt like I was deliberately being put in stressful situations, and then, when I cracked, it was like, ‘See? See? That guy’s crazy.’ But it’s like, ‘I’m not crazy. I’m just reacting to an intensely stressful situation.'”
He added, “I wasn’t crazy. I wasn’t smoking crack. I was definitely stressed out. There were things that overwhelmed me, but not in the way that people are saying. I went to South Africa to find a safe place.”
