Michelle Obama and Dave Chappelle decried President Trump for making their lives as parents more difficult.
“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, 52, told the former first lady on her podcast, IMO, on Wednesday. “And my baby’s like, ‘Oh no! They’re not good at it, daddy.’”
“It’s a hard job. It’s a hard job, I’m trying to tell you people,” Obama, 62, replied.
“Just so I make sure I say this, your family was so incredibly graceful,” Chappelle added.
The comedian has three children with his wife Elaine, including two older boys—Sulayman and Ibrahim—and a younger daughter, Sanaa, who was born in 2009. They moved to a small town in Ohio in 2005 after Chapelle walked away from a lucrative $50 million contract for The Chappelle Show.
“We don’t live in Hollywood; there’s no paparazzi trying to get their picture,” he said on My Next Guest Needs No Introduction with David Letterman in 2020. “The community protects them in that sense.”
Obama’s two daughters—Sasha and Malia—were already teenagers by the time her family handed over the White House keys to Trump, 79, in early 2017. Even so, the former first lady said raising children was “terrifying.”
“I tell people, it makes sense not to have kids,” the former first lady said. “Absolute, complete, emotional sense. Don’t do it.”
Chappelle, who used his 2016 SNL monologue to implore America to give Trump a ”chance,” has further walked back his stance on the president a decade later.
“You’re joking, right?” Chappelle laughed when PBS asked how Trump was doing the second time around. “He’s, man, come on, man. Nobody wants to feel this way. I don’t think anybody wanted a war. They definitely didn’t want to arguably lose one,” he said.
“Being a president seems like an opportunity to be a very unifying force,” he continued. “And I feel like perhaps he squandered that opportunity, to put it lightly.”
The comedian also shredded the president for “weaponizing” some of his stand-up jokes.
“I did resent that the Republican Party ran on transgender jokes,” he told NPR in April. “I felt that they were doing a weaponized version of what I was doing,” which he insisted was “not what I was doing.”
Michelle Obama has said that her husband’s presidency altered the way she approached raising their daughters.
“There were some lines drawn. I had to raise them to be stand-up young people on their own, especially as the daughters of a former president,” she said in 2024. “But people are quick to cut a kid off if you don’t show up right and you’ve got a name behind you. You have to come correct.”
“I never felt my job was to create mini-mes, or create people who were going to live out some brokenness in me or fill some hole or to be my friend,” she explained. “As my girls joke, I always said—my favorite line was, ‘I’m not one of your little friends.’”
Both parents admitted that AI has made their jobs even more difficult and that they frequently get caught by their children for sending them fake, AI-generated videos.
“I’m getting that a lot; I am so foolish. I believe all this stuff; it’s a shame,” Michelle Obama said. “But it’s also a reminder of why we have to train them up and move out of the way.”
“We’ve got to trust that they have to find the courage now to figure it out. It’s not our courage anymore,” she continued. “We can’t supplant our courage for theirs.”
