Key Takeaways

Michelle Obama has invited many fascinating guests on “IMO,” but few seem to have stood out quite like Dave Chappelle. During a live taping of the podcast with her brother, Craig Robinson, at SXSW London, the former First Lady shared why the comedian — who appeared on the show just last month — was one of their favorites.

“Dave Chappelle is one of the smartest people on the planet, the funniest, [as] all get out,” Michelle said on Tuesday (June 2), according to Variety. “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.”

At another point in the conversation, Michelle called Chappelle “one of [their] favorite guests” while discussing financial freedom.

Dave Chappelle’s “IMO” episode dug into money, fame, and walking away from millions

Money was one of the big topics that came up during Chappelle’s sit-down with Michelle and Robinson, which took place in Yellow Springs, Ohio, in front of a live audience. The comedian recalled jazz singer Johnny Hartman visiting his grandmother’s house when he was 8 years old and telling him he’d be “funny for money.”

He also spoke about walking away from $50 million after leaving “Chappelle’s Show” and the toll that decision took on his mental health. About 70 minutes into the conversation, the Half Baked actor explained why he’s “never really worried about money,” choosing to upgrade the town he lived in instead of his lifestyle. Take a look below.

Michelle Obama explains why she never expected “IMO” to become part of her next chapter

Another interesting talking point from Michelle’s “IMO” taping at SXSW London was how she never pictured herself hosting a podcast. After all, just over a decade ago, she and Barack Obama were living in the White House with their two daughters.

“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. Clearly, it turned out to be a great decision, considering the podcast has amassed millions of views and welcomed guests like Katt Williams, Angel Reese, and Keke Palmer, to mention a few.