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Michelle Obama

Michelle Obama reveals her surprising pick for favorite podcast guest

The former first lady revealed that controversial comedian Dave Chappelle has been one of her favorite podcast guests on her "IMO" podcast.

June 2, 2026, 11:39 a.m. ET

Everyone has their problematic fave, and Michelle Obama may be spilling the beans on hers.

The former first lady and podcaster revealed one of her favorite podcast guests during a live recording of her "IMO" show at SXSW London on Tuesday, June 2.

Obama, 62, launched her "IMO" podcast with her brother, Craig Robinson, last March. The podcast is produced by Higher Ground Productions, Obama's production company with longtime husband and former President Barack Obama.

Since the podcast's premiere, Obama and Robinson have interviewed a who's who of Hollywood A-listers, including Bruce Springsteen, Dwyane Wade and Gabrielle Union, Kenan Thompson, Carol Burnett and Jimmy Kimmel.

Michelle Obama speaks onstage during the "IMO" live podcast at the 2025 SXSW Conference and Festival at Austin Convention Center in Austin, Texas, on March 13, 2025.

But for Obama, comedian Dave Chappelle is a cut above the rest.

"Dave Chappelle is one of the smartest people on the planet, the funniest," Obama said at SXSW London, per Variety. Obama and Robinson's interview with the outspoken comedian was released on May 6. The pair traveled to Yellow Springs, Ohio, for the wide-ranging chat, which included candid discussions of Chappelle's early life, comedy career and his controversies with the LGBTQ community.

"Once he became himself, he moved back, bought a farm and has raised his family on this farm," Obama continued. "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, an Emmy-winning comedian and actor, has been criticized and faced accusations of transphobia in recent years due to his provocative jokes about the transgender community.

In a 2021 Netflix special, "The Closer," the comedian sparked backlash after saying "gender is a fact" and calling himself "team TERF," a term meaning trans exclusionary radical feminist. TERFs "deny the validity of transgender people and transgender identities," Sarah McBride, former national press secretary for the Human Rights Campaign, told USA TODAY at the time.

During the same special, Chappelle also defended J.K. Rowling, the "Harry Potter" author who has similarly been criticized for her anti-trans statements. He maintained, though, that he has "never had a problem with transgender people." Some Netflix employees staged a walkout in 2021 over Chappelle's special, but the streamer stood by him.

Dave Chappelle attends the 51st AFI Life Achievement Award: A Tribute to Eddie Murphy at Dolby Theatre in Hollywood, California, on April 18, 2026.

"People would think it's me vs. the gay community. I never looked at it like that," Chappelle, 52, told Obama and Robinson during his "IMO" appearance. "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."

Chappelle's 2023 special, "The Dreamer," also took a jab at the trans community during a joke where he described meeting Jim Carrey but being frustrated because the actor refused to break character as Andy Kaufman, who he was playing in the film "Man on the Moon."

In his conversation with Obama and Robinson, Chappelle largely took aim at the media for allegedly sensationalizing the nature of his jokes. "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 said. "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."

Contributing: Brendan Morrow, USA TODAY

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