Why Dave Chappelle’s SNL Monologues Fall Short of Their Potential

The iconic stand-up comic has a knack for saying just enough to maintain the illusion of being an enlightened, independent thinker. Many see through it.

Since his return to stand-up comedy following his infamous hiatus, Dave Chappelle has cemented himself as this generation’s voice of reason—a comedian philosopher, if you will, much like the iconic George Carlin once was. Whether through stand-up specials, interviews, or his recurring appearances on Saturday Night Live, Chappelle’s perspectives are consistently sought after to help reflect upon the chaotic landscape of contemporary politics and culture. And beneath it all lies an unspoken expectation: that he’ll make us laugh while holding up a mirror to a society that seems to have lost its way.

Over the past decade, Chappelle has hosted Saturday Night Live four times, each appearance correlating with significant political events. He made his hosting debut in November 2016, just days after Donald Trump’s shocking election victory. In his monologue, Chappelle tackled the aftermath of the election, touched on racial issues involving the Black Lives Matter movement, reflected on Obama’s presidency—remarking, “Obama did a good job. I think we’ll all miss him when he’s gone”—and extended an olive branch of cautious optimism toward Trump’s incoming administration. “I’m wishing Donald Trump luck,” he said, “and I’m going to give him a chance. And we, the historically disenfranchised [black people], demand that he give us one too.”