Dave Chappelle once did a sketch on his Comedy Central Chappelle’s Show in which he impregnated Oprah Winfrey and happily let her become his sugar mama; in another skit, he was questioned by a James Lipton type. Now, over the past two weeks, he’s sat for straight interviews with the real versions. So which inquisitor won the I Got Dave to Give It Up About His Big Walkout sweepstakes?
Invariably Oprah, because while Lipton shepherded a fawning but enjoyable overview of the comedian’s entire life/career, going deep on Half Baked, he avoided digging into the Africa business, even though Chappelle arrived ready to vent. Some of his proclamations — that the entertainment industry must be sick if it forces people like him to walk away from a $50 million contract — were also aired on Oprah, but Winfrey, like the hard-nosed interviewer she’s become again since dismantling James Frey, kept trying to get Chappelle back to facts and emotional specifics: Yeah, well what happened? Did someone do something? What was the tipping point?
When Chappelle’s disgust over reports of drug use and mental illness led him to scoff at a friend’s comment to the press that he wasn’t well, Winfrey admirably burst his everyone’s-out-to-get-me bubble and reminded him that it sounded like he wasn’t well: not crazy, maybe, but incredibly, legitimately stressed out over the atmospheric shift around his moneybags status. (And let’s get some perspective:When you flee the country and don’t tell your friends, wife and kids, nobody thinks it’s normal.)
But most fascinatingly, Winfrey and Chappelle seemed to be caught up in a rare, televised super-celebrity therapy session over fame and business and social responsibility, capped by a memorable moment when the talk show host stopped her guest cold as he started to wax idealistic about giving some of his newfound riches back to “the people.”
Calmly but sternly, Winfrey — who’s been rich a lot longer — warned, “Be careful, you need boundaries, you’re on national television.” In a sense, Oprah gave Chappelle the advice version of his kept-boy sketch: What wet-behind-the-ears $50-millionaire wouldn’t want to be taken under the wing of the billionaire empress of show biz?