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.”
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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?