Medcalf: Will Dave Chapelle’s return to Minnesota reveal a change of heart?

In his latest special, “The Unstoppable,” Dave Chappelle opens with a clip that shows a vulnerability he’s rarely revealed. With his mother, a former college professor, in the balcony of the arena, he said he never felt tough when he was a kid. He cried a lot. He was often hurt.

But it was the next thing he said that preceded his planned trip to Grand Casino Arena in St. Paul on Monday, Feb. 16, with Grammy-winning rap group Clipse: the arrival of the National Guard in Washington, D.C., and what he called an attempt to “take the chocolate out of Chocolate City,” referencing the nickname of the nation’s capital in the Black community.

“This is not the only city this is happening in,” he said. “It’s happening in California. It’s happening in Oregon. It’s happening in Illinois and it’s happening in Memphis.”

In the Twin Cities, he said his mission is to support the fight against ICE and “to stand with a community at the center of events that should unite all Americans in defense of civil rights, human dignity and the principles we claim to hold sacred.”

The last time Chappelle came to Minneapolis, he’d been steeped in controversy.

Now Chappelle is back, perhaps for repentance, although his latest special makes that assumption questionable. The Twin Cities is his platform for his latest message. But is this show a performance — or just performative? We’ll know on Monday.

The unifying tone of the announcement about his arrival in a place he’s loved because of his connection to Prince was not the one presented during one of his most recent trips to Minnesota, on the heels of a series of specials that seemed to target the LGBTQ community. I wrote then that I wouldn’t see Chappelle’s show because my late cousin and others within his community faced actual danger from the jokes Chappelle had told.

Within the Black community, few professions have ever been granted a national stage to offer nuanced perspective on a chaotic world. The historic reverence for our musicians, religious leaders and comedians is tied to a discriminatory educational system that created barriers to achieving legitimate certification within a multitude of industries. So we created our own heroes.

Dick Gregory, Richard Pryor, Redd Foxx and Moms Mabley opened a door that Wanda Sykes, Kevin Hart, Chris Rock, Eddie Murphy and Chappelle have all walked through to command massive audiences and millions of dollars for their comedic acts.

I love Chappelle, I love comedy and I love those comedians who’ve all been icons to me. The best comedians can make us laugh and think, they can add levity to the incomprehensible, they can build us up when we’re most fragile, all with a few jokes. I am admittedly a hypocritical consumer of their acts, as I take the parts I enjoy and discard the rest, as I yearn for them to use their posts for good.

Chappelle will arrive with my favorite hip-hop group, Clipse, with an opportunity to offer a community full of wounded people a chance to laugh. But only if he has changed. That’s the part I wrestle with.

It’s easy to use Minneapolis as a place to be reborn right now. Politicians, celebrities, influencers and others have once again made the current climate the foundation of whatever they’re selling — because they’re always selling and promoting. I digest their pleas and promises with caution.

To close the door on those who may decide to change is understandable. Because a seemingly converted ally can be a source of harm. It also ignores the possibility that their turn is real.

I will be there on Monday to see if this applies to Chappelle, mostly because it’s a chance to hang out with my best friend and see my favorite hip-hop crew. Chappelle isn’t the main event for me. I am hopeful that the tenor of his announcement will carry over into whatever 2026 looks like for him.

He has a stage and a following of folks who will listen to him, and if he decides to use all of that influence to pursue peace and empathy, he can do more good with his bit than he has in recent years.