Michelle Obama Calls Dave Chappelle One of Smartest

Michelle Obama said her podcast IMO helped her step into something she never planned to do, then singled out Dave Chappelle as one of her favorite guests—while also revisiting the comedy backlash he has faced.

Michelle Obama didn’t sound like she was trying to impress anyone when she talked about why hosting a podcast felt so unfamiliar in the first place. During a live IMO recording at SXSW London on Tuesday. June 2. the former First Lady told Craig Robinson that taking on a podcast wasn’t in her original life plan—yet she felt pulled toward it anyway.

“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 said. “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 followed it with the line that clearly stuck with her: “I figured, if I can be First Lady, I can do a podcast with my brother!”

IMO launched in March 2025. and since then the show has welcomed a wide range of guests. including Jimmy Kimmel. Jamie Lee Curtis. Conan O’Brien. Halle Bailey. Dave Chappelle. and more. But in the middle of that long list. Michelle made it clear she had her own favorites—and Dave Chappelle was at the top of that group.

During the SXSW London event, Michelle singled him out as one of the podcast’s standout guests. “Dave Chappelle is one of the smartest people on the planet, the funniest, all get out,” she said.

She then pointed to a specific personal arc she associated with him: “Once he became himself. he moved back. bought a farm and has raised his family on this farm.” Michelle added that one of the questions she and the conversation had touched on was “Why here?”—and she repeated Chappelle’s answer: “I wanted to have the financial freedom to be courageous.”.

For Michelle, it landed as a message she wanted to pass on. “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 conversation didn’t stay in compliments for long. Per the account discussed during the event, Michelle and Craig asked Dave about the controversy tied to his jokes targeting transgender people in some of his comedy specials. Chappelle pushed back on the way the issue is often framed.

“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. 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.”.

He also spoke about what gets lost when a joke is judged from a distance. “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.”.

That live recording captured a familiar tension in celebrity conversation—how someone can be celebrated for sharp intelligence and comedy. while also being pressed about the reactions their work has sparked. Chappelle’s presence on IMO has become part of that larger story: what Michelle Obama values in a guest. and how deeply those conversations can go.

Michelle Obama IMO podcast Craig Robinson Dave Chappelle SXSW London podcast guests comedy controversy transgender jokes Jimmy Kimmel Jamie Lee Curtis Conan O’Brien Halle Bailey