Dave Chappelle and Michelle Obama take jabs at Trump in ‘IMO’ interview: ‘Tried to tell the people’

In a near two-hour conversation the comedian, Craig Robinson and former First Lady dive into several subjects, from Chappelle’s upbringing to parenting in 2026.

Comedian Dave Chappelle famously wished for President Donald Trump to do right by the country when he was elected for his first term in 2016. A decade later, the 52-year-old has different views on Trump, echoed by members of his own family — and Michelle Obama.

The former First Lady and her brother Craig Robinson traveled to Ohio to interview Chappelle for their “IMO” podcast and through a candid, near two-hour conversation, the three discussed how Chappelle’s stepmother laid down the precursor to the #MeToo movement, how his mother was a “greatness whisperer” and how their children are growing up in a world with AI and more.

Including how Trump has made parenting a bit more difficult in both their respective households.

“I was trying to explain to somebody, I’m like, ‘You know, my daughter is 16, so Donald Trump is the first white president she’s ever seen,’” Chappelle said in the interview which premiered on Wednesday. “And my baby’s like, ‘Oh no! They’re not good at it, daddy!’””

After laughter died down in the room, Mrs. Obama chimed in.

“It’s a hard job,” she said. “Tried to tell the people. It’s a hard job.”

Chappelle offered a moment of reflection for the Obama years, saying the family was “graceful” and compared their time in the White House to the recent Artemis II mission of Victor Glover.

“You in particular, I believe, did more to humanize what a presidency is than maybe anybody ever,” he told Obama. “You’re the first person that I feel like I could know that’s been in that space and, you know, survived it and came out as gracefully as you went in. So I really, really, really appreciate you and your family and your presence.”

Obama and Chappelle remain optimistic about the future, with the former First Lady hoping that the generation that is preparing to use their voice in upcoming elections and in general society will do things for the greater good and be compassionate in the process.

“We’ve got to trust that they have to find the courage now to figure it out,” Obama said of the next generation. “It’s not our courage anymore. We can’t supplant our courage for theirs and these times are going to be, that’s going to play itself out. It may seem scary now, but we have to have faith that they will figure this out and be able to tap into the values that we’ve instilled in them in communities like this, that they’ll remember humility and boundaries and love and trust and all of that. That compassion has to go into whatever the solution is.”

That compassion has been tested plenty by Trump over the past decade when it comes to the Obama family, from sharing AI videos of the couple depicted as apes to recently calling for the 44th president to be arrested for “treason.” Although he often plays the high road when it comes to Trump, the former president admitted to The New Yorker that the man who followed him in the White House has caused occasional discord at home.

“It does create a genuine tension in our household, and it frustrates her,” Barack said of Michelle’s feelings about the relentless calls for him to weigh in on Trump’s presidency. “I’m more forgiving of it, in the sense that I understand why people feel that way, because people aren’t looking at me in historical comparison to other Presidents.”