Michelle Obama, 62, praised Dave Chappelle as “one of the smartest people on the planet” during a live recording of her “IMO” podcast at SXSW London on June 2, drawing renewed attention to the comedian’s long-running controversies involving the LGBTQ community
When Michelle Obama walked into the live recording on Tuesday, June 2, at SXSW London, she didn’t just praise Dave Chappelle for being entertaining. She framed him as something sharper than that.
Obama—62—said the comedian is “one of the smartest people on the planet, the funniest,” during her “IMO” podcast taping, as the show’s audience watched her and her brother, Craig Robinson, set up another wide-ranging conversation.
The moment landed at a time when Chappelle’s cultural impact has been inseparable from the arguments around him—especially after years of criticism tied to provocative jokes about the transgender community.
Obama’s “IMO” podcast. launched with Robinson last March. is produced by Higher Ground Productions. the production company Obama runs with longtime husband and former President Barack Obama. Since the podcast’s premiere. Obama and Robinson have interviewed major entertainment figures. including Bruce Springsteen. Dwyane Wade and Gabrielle Union. Kenan Thompson. Carol Burnett and Jimmy Kimmel.
But when it came to Chappelle, Obama didn’t speak like a host rattling off a guest list. She described the appeal as something personal and rare—then pointed to the way he built his life after becoming “himself.”
“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. ” Obama said. In the broader conversation. she also recalled that once Chappelle “became himself. ” he “moved back. bought a farm and has raised his family on this farm.”.
The Chappelle episode itself was recorded as Obama and Robinson traveled to Yellow Springs, Ohio, for a conversation released on May 6. Their interview included candid discussions of Chappelle’s early life, comedy career, and controversies with the LGBTQ community.
Chappelle. an Emmy-winning comedian and actor. has faced accusations of transphobia in recent years. rooted in comments he made about the transgender community. In a 2021 Netflix special. “The Closer. ” he sparked backlash after saying “gender is a fact” and calling himself “team TERF. ” a term meaning trans exclusionary radical feminist. Sarah McBride. former national press secretary for the Human Rights Campaign. said at the time that TERFs “deny the validity of transgender people and transgender identities.”.
In that same special, Chappelle defended J.K. Rowling, the “Harry Potter” author who has also been criticized for anti-trans statements. Chappelle maintained. though. that he has “never had a problem with transgender people.” Some Netflix employees staged a walkout in 2021 over “The Closer. ” but the streamer stood by him.
When Obama and Robinson sat down with Chappelle for “IMO,” the comedian, 52, pushed back on how his remarks were interpreted. “People would think it’s me vs. the gay community. I never looked at it like that,” he told Obama and Robinson. “I always thought it was corporate interest and culture negotiating itself.”.
He added a pointed image of how critics engaged with his work: “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.”.
The push and pull between Chappelle’s defenders and critics has not been limited to “The Closer.” His 2023 special. “The Dreamer. ” also drew attention for a joke where he described meeting Jim Carrey. then being frustrated because the actor refused to break character as Andy Kaufman. who he was playing in the film “Man on the Moon.”.
During the “IMO” conversation, Chappelle largely directed the argument toward media coverage. “Nothing makes a comedian madder than reading his joke wrong in the paper,” he said. “The intention of a comedy show is a very unique intention,” Chappelle added. “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’ve got to have a margin of error.”.
The sequence—Obama’s praise at SXSW London. her emphasis on Chappelle’s intellect and life decisions. and the recurring debate over how his jokes land—shows how entertainment can be both deeply personal and deeply contested at the same time. For Chappelle, the dispute has often come down to interpretation. For critics, the issue has often been the content itself.
As Obama’s “IMO” episode continues to circulate—released May 6 after her and Robinson’s trip to Yellow Springs, Ohio—the contrast between her admiration and the backlash that has followed Chappelle for years is difficult to ignore.
Michelle Obama IMO podcast Dave Chappelle SXSW London Higher Ground Productions Craig Robinson Yellow Springs Ohio Netflix The Closer LGBTQ controversy transphobia allegations media interpretation