Michelle Obama Calls Dave Chappelle 'One of the Smartest, Funniest People on the Planet' Despite His Controversies

Michelle Obama and brother Craig Robinson have talked to countless celebrities since they launched their "IMO" podcast in March 2025, but it was easy for the former first lady to pick a standout.

While speaking on the topic of financial freedom during their "IMO Live" at SXSW London conversation held Tuesday, June 2, Obama named Dave Chappelle as “one of our favorite guests.”

Obama, 62, and Robinson, 54, headed to Chappelle's hometown of Yellow Springs, Ohio, to record the episode, which aired last month.

“Dave Chappelle is one of the smartest people on the planet, the funniest, all get out,” she said during the event. “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.”

Chappelle's jokes about trangender people have caused controversy.

When the podcasting pair asked him about the situation, Chappelle, 52, said the media has gotten his comedy "wrong."

“People would think it’s me vs. the gay community," Chappelle noted. "I never looked at it like that. I always thought it was corporate interest and culture negotiating itself. So 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.”

He continued, “Nothing makes a comedian madder than reading his joke wrong in the paper. And reading a joke is nothing like hearing one or being one, and the intention of a comedy show is a very unique intention. We are playing with whatever the culture is made of, and we break it down and we get it right or we get it wrong. But in all art, if it’s going to be good or even hopefully great, you gotta have a margin of error.”

Obama released her memoir, Becoming, in 2018, before going into podcasting through her and Barack Obama’s Higher Ground productions.

“It’s that courageous thing, right?" she said. "The feeling that, OK, I guess we can do this because we did all these other things. The bravery makes you brave to try anything at any age. I mean, I lived in the White House. I was the first lady. That wasn’t my plan, I had no training for that. Wasn’t my idea! But we figured it out.”

She continued, “I figured, if I can be first lady, I can do a podcast with my brother!”