It’s hard to believe it’s been eight years since Dave Chappelle walked away from a $50 million contract and the title of Funniest Man Alive to pursue a life of relative quiet and anonymity. Even if he had grown tired of and troubled by his hit Comedy Central program “Chappelle’s Show,” he had ascended to the highest echelon of comedy auteurism, making his creative options endless. Instead, intermittent stand-up performances are the only glimpse the public has had of Chappelle, whose complicated mystique now encompases a whole range of emotions beyond just humor.
For fans who have waited the better part of a decade to catch Chappelle’s act, the wait is almost over. He debuts a headlining stint along with Flight of the Conchords when the “Oddball Comedy and Curiosity Festival” kicks off Friday in Austin, Texas. And thanks to a heretofore unseen streak of self-aware humor from fellow creative eccentric Prince, Chappelle’s profile is the highest it’s been in years.
It might not have achieved “I’m Rick James B**ch!”-levels of pop culture ubiquity, but the “Chappelle’s Show” sketch about the time Charlie Murphy played basketball with Prince was definitely a highlight of the show. Over the weekend, Prince repaid the homage by placing Chappelle’s hilariously deadpan visage on the cover of his new single “Breakfast Can Wait.” Less than a week after joining Twitter, Prince is already rewiring his public image as someone much funnier and in-the-know than his guarded, aloof persona of the past.
From the sound of a recent New York Times article that previews some of the material he’s been performing in the lead-up to his new tour, addressing his public persona will be one of the topics of Chappelle’s act as well. “His characteristic laid-back delivery and pinpoint timing were in service of jokes that were more dark, intricate and revelatory than his stand-up from a decade ago,” the Times writes. “Mr. Chappelle might have left television, but that departure has become the wellspring of his comedy now. He only needs a microphone and a stage to lay claim to greatness.”
The article outlines a number of bits Chappelle performed at Richmond, VA club in June and says that “his jokes now always seem to circle back to his infamous exit from Comedy Central, explicitly or, more often, implicitly.” Detailing a bit where Chappelle tells his son that “it’s O.K. to quit,” it seems that Chappelle has achieved peace with his controversial decision to walk away from the spotlight at the height of his fame and is cleverly mining his audience’s intrigue with the subject for laughs.
The article is rhapsodic in its assessment of his new material. Chappelle’s bit about his encounter with a homeless man is described as having “the poetic weight of an August Wilson monologue” and his style is characterized as having become “increasingly distinct from a typical comedy club set, forging his own way forward.”
“An extremely patient comedian, Mr. Chappelle is now making a commitment to establishing scenes, mapping out descriptions of characters that are almost literary in their detail.”
From the sound of the story, Chappelle has used his hiatus from the public eye to carefully hone his craft. Audiences in Austin on Friday will be among the first to discover the fruits of that labor.