When Jimmy Kimmel Was Embarrassed 'Really Bad' in Front of Michelle Obama on 'The Ellen Show'

Jimmy Kimmel couldn't say he made the best first impression while meeting the former First Lady Michelle Obama. The comedian appeared on The Ellen Show back in 2018 when Ellen DeGeneres reminded him of a particular skin-tight ice skating dress. Kimmel affirmed and shared how he was forced to greet Obama in that embarrassing costume as she was waiting for him backstage. 

Kimmel recounted he donned the getup as a birthday surprise for DeGeneres who turned 60 that time. The TV host showed up in an ice-skating dress with skates and all the gear and it was all fun and games until he was summoned by Obama. The comedian, who definitely wasn't dressed for the meeting, had no choice but to show up to the attorney looking funny. 

"I go back to my dressing room, and the First Lady, Michelle Obama, was here, and they said, 'Mrs. Obama would love to say hello to you before she goes out to do her segment on Ellen,'" Kimmel shared the story. "Which means I have to go in there dressed like that. Yes. That's right. And really, nothing is left to the imagination. Top five most embarrassing moments of my life. That was bad. That was really bad. I feel like I should be deported for that," as per Vanity Fair. 

Well, it seems Kimmel doesn't have to overthink what Obama would've thought of him since she has quite a sense of humor herself. Back in 2021, she showed up on his late-night show Jimmy Kimmel Live talking about all things quarantine, their daughters, Sasha and Malia, and ahem, her and ex-president Barack Obama's sex life. 

As Kimmel was going through the motions of the interview, he popped the single most annoying question to Michelle: "On the night that Seal Team 6 took out Osama Bin Laden at your husband's order, did you and your husband make love that night to celebrate?" The now-60-year-old turned the tables on him and roasted Kimmel, "You know, I have to tell your audience that for some very sick reason, you're very obsessed with this question of that major historical event," as per Vulture. 

She continued, "In the history of aaaaaalll the conversations I've had — anybody drilled down on this particular point like you, Jimmy Kimmel. So I turn that back on you." However, she didn't just stop there, "That's what you want to know. You're still that little boy in your bedroom under the cover with the flashlight going, I hope nobody sees me," mimicking the flipping of a Playboy magazine. 

The 56-year-old has interviewed Obama a couple of times on his show and ran into her during multiple events. But his roasting hasn't been limited to the show. Kimmel once posted his hilarious take on the #Promchallenge on X, formerly Twitter in response to the president's wife's post. "Throwing it back to my 1982 prom night and this pink satin, polka-dotted dress," wrote Michelle while attaching a throwback photo of herself from her prom days.

Kimmel, on the other hand, was his goofiest self and posted his hilarious contribution to the #Promchallenge and captioned, "I didn't go to prom - or homecoming - or girls reverse - but my friend (and now bandleader) @Cleto_III let me sleep with him that night anyway."