Screenshot of Caitlyn Jenner and Jimmy Kimmel from the show 'Jimmy Kimmel Live.' (Cover Image Source: YouTube | Photo By @JimmyKimmelLive)
Caitlyn Jenner is no stranger to controversy but during an appearance on ‘Jimmy Kimmel Live!,’ she turned the tables on the late-night host, calling him out for past jokes about her transition. The moment, though brief, created palpable tension between the two as Jenner confronted Kimmel on live TV.

During the interview, Jenner opened up about her journey, including the challenges of coming out to her family and the intense media scrutiny that followed. When discussing how she informed her children about her transition, Jenner made a pointed remark at Kimmel himself. As per Digital Spy, she remarked, “I slowly told all my children. Because it had just been hammered all over the media for the longest time. In fact, guys like you…making some jokes.” Kimmel caught off guard, argued, “We didn’t know what was happening.” But before he could continue, Jenner interjected, “Now he is going to apologize! It’s alright, I accept your apology.”

Jenner explained, “Kris and I, we had gone our separate directions, not because of gender issues but because of other things, and there I was back in Malibu all by myself.” As per Entertainment Weekly, while the exchange was playful on the surface, there was an undeniable edge to it. Kimmel quickly moved the conversation along, even taking the opportunity to shift some blame onto his late-night rival. In response, Jenner assured, “You’ve always been my favorite.”

Beyond discussing her transition, Jenner and Kimmel also touched on their family dynamics. She confessed, “Some [of my children] I have remained very close to…A couple of them… I am a little more distant. I have to admit, I will sit…and wonder, ‘Is it because of my transitioning? Or is it because their life is so busy that they don’t call, like, all the time?’”

Jimmy Kimmel called Caitlyn Jenner an “ignorant a-hole” when she made comments about the homeless in California during an interview with ‘Fox New’s Sean Hannity. #THRNews pic.twitter.com/s8R87Pt7q5

— The Hollywood Reporter (@THR) May 7, 2021

The tension between Jenner and Kimmel wasn’t just limited to this one interview. On another occasion, Kimmel addressed Jenner’s remarks about homelessness in California. Jenner had previously stated in an interview with Sean Hannity that a wealthy friend of hers was leaving the state because he couldn’t ‘take it anymore’ after seeing homeless people on the streets. “The guy right across, he was packing up his hangar. And he says, ‘I’m moving to Sedona, Arizona. I can’t take it anymore. I can’t walk down the streets and see the homeless.’” Reflecting on the same, Kimmel slapped back, “Is it transphobic to call a trans person an ignorant a–hole? Or does calling that trans person an ignorant –hole— even though she happens to be a trans person— show that we don’t discriminate against ignorant assholes, no matter their gender orientation? It’s a tough one. I don’t know. I guess we will let the internet decide tomorrow.” His biting commentary quickly went viral.