The world of comedy has long been dominated by liberal entertainers. With a few exceptions, including Bob Hope, Jack Benny, Sheryl Underwood, Jamie Farr, Jeff Foxworthy, Dennis Miller, Joan Rivers, and Jackie Mason, most of the funny men and women on stage just aren’t on our side.
This doesn’t mean the political Right can’t appreciate left-leaning comedians who push the envelope and challenge societal norms. In particular, Dave Chappelle’s unique brand of comedy has his share of conservative fans — including me.
Chappelle, who is in the midst of a career comeback with a three-part special on Netflix, is a comedic genius. The 43-year-old’s stage presence, laser-sharp focus on current issues, outside-the-box thinking on race relations, and strong support for free speech make for a lethal combination. He doesn’t believe the political Left necessarily has all the answers, either.
This has been evident during his time on the comedy-club circuit, as well as various TV cameos (Home Improvement, The Larry Sanders Show) and movie roles (Robin Hood: Men in Tights, The Nutty Professor).
Yet it was his groundbreaking sketch-comedy series, Chappelle’s Show (2003–06), on Comedy Central, that really opened the eyes of many to the immense talent of this great performer.
Some of his memorable sketches included: “Frontline,” starring Clayton Bigsby, the blind black white-supremacist; “Charlie Murphy’s True Hollywood Stories,” which involved a pick-up game of basketball against Prince and the wild evenings of singer Rick James; “The Niggar Family,” about a white household living in an Ozzie and Harriet-type community with an eyebrow-raising last name; and the ever-lovin’ crack addict, Tyrone Biggums.
I’ve never laughed harder in my life than I did at some of his comedy routines. I still watch the DVD box set of his show, which he abruptly walked away from (along with a $50 million deal) and went to South Africa after reports of burnout, frustration, and loss of creative control. The episodes never grow old.
Sure, Chappelle’s comedy is politically edgy at times. He’s expressed some concerns about Republicans and conservatives. He never cared for George W. Bush, and he created a “Black Bush” character to juxtapose what White America and Black America could potentially get away with.
At the same time, he’s not a knee-jerk liberal. Far from it.
During a comedy set last year, Chappelle mentioned that he found the language contained on then–GOP presidential candidate Donald Trump’s leaked 2005 Access Hollywood video to be “gross.” At the same time, “the way I got to hear it was even more gross. You know that came directly from Hillary.” When he begrudgingly admitted that he voted for Clinton, he reportedly didn’t “feel good” about it and said, “She’s not right and we all know she’s not right.”
This initially caused some conservatives to speculate that Chappelle’s views about Trump had changed. He quickly put this theory to rest on TMZ just before the presidential election, stating “Jesus Christ, I’m not a Trump supporter.” (That being said, he did wish the president well after his victory and said he was “going to give him a chance.”)
The Daily Beast’s Amy Zimmerman wrote in a November 8 piece, “In the year of the political renegade, Chappelle is a fittingly loose cannon.” It was a predictable left-wing response to a celebrity who admitted that he wasn’t on Team Democrat with every ounce of his being. Heaven forbid he should be allowed to hold a contrarian opinion to the vast majority of the celebrity mob, right?
He even got lambasted after two Netflix specials, The Age of Spin: Live at the Hollywood Palladium and Deep in the Heart of Texas: Live at Austin City Limits, were released on March 21. The gay community was displeased that he made jokes about them, and the trans community took offense to this remark about Caitlyn Jenner: “Whenever I see one of them T’s [i.e. transsexuals] on the street, I’m like ‘I don’t mind them but man I miss Bruce.’”
To the comedian’s credit, he did warn his audience to “man the f*ck up or you’re not going to make it through this show.”
If anything, Chappelle’s personal mission in comedy is to seek the truth, even if it hurts. He refuses to be constrained by political correctness and hurt feelings. Rather, he wants his audience to think, consider, debate, discuss, argue, and react to the world we live in. There are many sides to a particular story, and each one needs to be investigated intelligently, forcefully — and above all, humorously.
That’s something many conservatives support, and should always support in a liberal democratic society — even if it took a liberal comedian to remind us of this fact.