Michelle Obama Praises Dave Chappelle as 'One of the Smartest People on the Planet' During Podcast Discussion

Michelle Obama has shared her thoughts on hosting a podcast alongside her brother Craig Robinson, spotlighting some of the notable figures who have appeared on their show, IMO.

The former First Lady and her co-host took part in a live recording of their podcast at SXSW London on June 2, discussing the journey since the program's debut in March 2025. During the event, Michelle reflected on how stepping into the podcast world felt like a natural extension of her willingness to embrace new challenges.

"It's that courageous thing, right? 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," she explained. "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 with a lighter note: "I figured, if I can be First Lady, I can do a podcast with my brother!"

Since launching, IMO has featured an impressive roster of guests spanning entertainment and culture, including Jimmy Kimmel, Jamie Lee Curtis, Conan O'Brien, Halle Bailey, and Dave Chappelle, among others.

When discussing standout conversations, Michelle specifically called out Chappelle for his intellect and humor. "Dave Chappelle is one of the smartest people on the planet, the funniest, all get out," she said. "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."

During the conversation, Michelle and Craig broached the subject of the backlash Chappelle has faced regarding jokes about transgender people in his comedy specials. The comedian offered his perspective on the matter, explaining that he viewed the discourse as broader cultural negotiation rather than conflict with any particular group.

"People would think it's me vs. the gay community. I never looked at it like that. I always thought it was corporate interest and culture negotiating itself," Chappelle said. "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 elaborated on the nuances of comedy performance and interpretation. "Nothing makes a comedian madder than reading his joke wrong in the paper. You know, 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."