Michelle Obama Shows Love for This Controversial Comedian: 'One of the Smartest People'

It's been a decade since Barack Obama left the White House, but he and the former first lady have remained in the spotlight in a number of ways.

For one, Michelle Obama has run a successful podcast with her brother Craig Robinson. And on Tuesday, June 2, the pair brought a live recording of IMO to SXSW London to discuss their work - including one of their favorite guests, which may catch fans by surprise.

They've interviewed guests including Jamie Lee Curtis, Jimmy Kimmel, Steph Curry, Conan O'Brien and more...

But during the SXSW London conversation, Variety reports, Michelle, 62, revealed that Dave Chappelle has been "one of our favorite guests," praising the controversial comedian as "one of the smartest people on the planet, the funniest, all get out."

Michelle continued, "Once he became himself, he moved back, bought a farm and has raised his family on this farm. One of the questions was, ‘Why here?' And he said, ‘I wanted to have the financial freedom to be courageous.' And I was like, ‘Bars,' you know? And that's the truth, and what I would say to young people and to my girls: Live smaller than you need to."

The comedian, 52, has made headlines in recent years for his jokes about transgender people. When asked about the subject on IMO recently, Chappelle said the media has gotten his comedy "wrong," per Variety.

"People would think it's me versus the gay community. I never looked at it like that," Chappelle said during last month's episode. "I always thought it was corporate interest and culture negotiating itself. So, you know, most of those people who were critical of what I was doing didn't seem like they were of it. It's like they had their faces pressed against the glass, commenting on what we were doing in there, but they weren't in there doing it."

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This story was originally published June 2, 2026 at 10:19 AM.