The Shady Side Of Jimmy Kimmel

For one of America's most beloved late-night hosts, Jimmy Kimmel has been known to throw his fair share of shade. He has criticized Hollywood heavyweights and political figures both on air and off, and he's also been known to make some serious errors in judgment in front of millions. Some, like Newsweek, have even called Kimmel "uncancelable" despite the seeming lapses in judgment to the contrary over the years.

But the comedian — whose long-running late-night staple "Jimmy Kimmel Live!" began in 2003 — has been able to keep all eyes on him; even when he couldn't believe it himself. "I still feel like the altar boy who is goofing on the priest," he admitted to the Los Angeles Times. "I think that most people always think of themselves the way they have always thought of themselves. I'm as surprised as anyone could be in this position — even to have a really good job is a surprise to me." While such a seasoned comedian having this kind of self-doubt could seem unfathomable, it could also be justified, considering all of the gaffes and public scrutiny Kimmel has drawn over the years.

Before he was one of the kings of late-night television, Jimmy Kimmel co-hosted a more manly prime time hour. Alongside friend and comedian Adam Carolla, Kimmel created and led "The Man Show" on Comedy Central from 1999 to 2004. The quasi-talk-meets-sketch show has since faced criticisms over its content, which ranged from blatant misogyny to transphobia.

"I look back at every show I've ever done and cringe," Kimmel told Vulture of the show in 2017. "It was a show people loved, and I got to work with Adam [Carolla], which was a dream at the time, and we did a lot of funny stuff. We also did a lot of stupid stuff."

The program that spawned the all-female crew crudely named "Juggies" was also an early platform for prominent figures of the 2020s, including podcaster Joe Rogan, who took over for Kimmel as host when the co-creator exited the show in 2003. The New York Times even posed the question in 2020 of whether or not a revival of "The Man Show" would succeed in the post-#MeToo era. Kimmel's take? "It would be an even bigger hit than it was back then ... Because there's more back to lash against," he explained to Vulture. "There's more scrutiny. There's more political correctness. That always offers more opportunity to run counter."

While on "The Man Show," Jimmy Kimmel performed in a sketch that resurfaced to much backlash years later. In the clip, Kimmel sports blackface and full-body paint as he portrays NBA legend Karl Malone, something that he continued from his days in the '90s at the Los Angeles radio station, KROQ.

"I never considered that this might be seen as anything other than an imitation of a fellow human being," Kimmel said in a 2020 statement (via Deadline). "It is frustrating that these thoughtless moments have become a weapon used by some to diminish my criticisms of social and other injustices."

Kimmel's retroactive statement, though almost two decades after the sketch in question first aired, also focused on how he would not let his past actions dictate his continued work and personal beliefs. "I believe that I have evolved and matured over the last 20-plus years," he explained. "And I hope that is evident to anyone who watches my show. I know that this will not be the last I hear of this and that it will be used again to try to quiet me ... I won't be bullied into silence by those who feign outrage to advance their oppressive and genuinely racist agendas."

Just as he was preparing to transition from "The Man Show" to his very own late-night program, Jimmy Kimmel made way for a scandal. In 2002, he reportedly divorced his then-wife since 1988, Gina, to pursue a relationship with fellow comedian Sarah Silverman. According to a claim from Fox News, the pairing was "one of the worst kept 'open secrets' in Hollywood."

Kimmel and Silverman had been working in proximity in the industry after meeting at Comedy Central's "Roast of Hugh Hefner," where Silverman made jabs at her future beau's figure. "I didn't know him at all back then," she quipped to EW in 2003. "I can't believe I called him fat. Knowing him now it's funny because he has such a thin personality." While there was some rumored overlap between Kimmel's marriage and his relationship with Silverman, the comedic pair went on to date on and off from 2002 until 2009.

Even though they didn't last romantically, the duo have remained friends — or even family, according to Kimmel. "We're like brothers," he told GQ in 2017. "It doesn't make sense to me that people would erase a big part of their lives ... We have a lot of things in common and mutual friends. I'll see something in the news and think, 'Oh, my God. I have to tell Sarah about this.'"

One of the most popular segments from "Jimmy Kimmel Live!" is "Mean Tweets," where celebrities, athletes, and even politicians sit in front of the camera and read disparaging posts about themselves for millions at home and online to see. There have even been live versions of the segment over the years, boasting the likes of Benedict Cumberbatch, Tom Brady, and even former president Barack Obama.

But in one segment from 2014, the host seemingly went overboard with his comments to guest Sofía Vergara. As the two traded blows about the other back and forth, things got more and more heated until Kimmel crossed a line by reading one tweet that negatively insinuated that the actor was transgender. Vergara responded by slapping Kimmel in front of his studio audience and making her way off the stage in a huff. While it was clearly a pre-planned joke, numerous outlets picked up the story and shared the moment with millions worldwide. Neither Kimmel nor Vergara have commented on the moment since, but Vergara did have the last laugh: "[Mine's] for sure bigger than yours!"

For years, Jimmy Kimmel had a bone to pick with fellow late-night legend Jay Leno as a result of the now-storied Leno vs. Conan O'Brien takeover of "The Tonight Show." Kimmel — who was a friend of O'Brien's and a lifelong fan of Leno's other rival, David Letterman — opted to taunt the TV legend, throwing on-air barbs at the host and speaking ill of him in the press.

Kimmel's jabs continued for years, and he showed no signs of letting up. "I always feel bad if I hurt anybody's feelings, but I don't believe Jay Leno has actual feelings, and he doesn't seem to be that worried about other people's feelings," he quipped to Playboy (via ABC News) in 2013.

But in 2017, the two talk show juggernauts buried the hatchet after Kimmel's infant son was hospitalized. "Jay and I have made peace," Kimmel told The Hollywood Reporter's "Awards Chatter" podcast. "After my son had his operation, he called me and he was very nice." He even went so far as to compliment his former enemy: "You can't argue with [Leno's] success and his longevity. I will say, when I was in high school and college, he was one of my all-time favorite comics."

Even after his stint co-hosting "The Man Show," Jimmy Kimmel went on to make some disparaging comments at the expense of women. For example, in 2009, he made a crude sexual joke about an underage Megan Fox during an interview on "Jimmy Kimmel Live!" In the clip, Fox, who was promoting one of Michael Bay's "Transformers" films, was discussing what she had endured at the hands of the director during one of her earliest acting gigs at age 15. "I was wearing a stars-and-stripes bikini and a red cowboy hat, and, like, six-inch heels," she remembered. 

The actor further recalled how she wasn't allowed to sit at the bar in the scene because she was underage. "[Bay]'s solution to that problem was to then have me dancing underneath a waterfall getting soaking wet," she explained. "At 15, I was in 10th grade. So that's sort of a microcosm of how Bay's mind works." Kimmel's response? "Yeah well, that's really a microcosm of how all of our minds work," he uttered.

Even when the clip resurfaced on X, formerly known as Twitter, years later, users were quick to share their outrage. One responded to the video: "She's so clearly visibly upset by Kimmel's reaction but can't say anything to his awful joke ... It's a kind of abuse in real time. Even a high star celebrity is not immune."

Jimmy Kimmel was once known to make racist remarks, with some of them targeting the Asian community. In 2013, the comedian aired a China-focused edition of his popular "Kids Table" segment. When prompted during the pre-recorded roundtable discussion (via CNN), one child responded that to reduce global debt, the United States should "kill everyone in China." Kimmel responded, "Kill everyone in China? Okay, that's an interesting idea," then asked the group, "Should we allow the Chinese to live?"

The skit drew so much backlash that Kimmel himself apologized in person to the protestors outside of the El Capitan Theatre, where "Jimmy Kimmel Live!" is filmed. "If I upset you, I'm very, very sorry, " Kimmel pleaded to the crowd (via On Demand News). "I thought that everyone would see it as a joke."

Kimmel also came under fire for his criticism of the K-pop group BTS, likening their popularity to a "fever" reminiscent of COVID-19 during a 2022 interview with Ashley Park on "Jimmy Kimmel Live!" Needless to say, the online masses were quick to react. "Putting aside just how massively tone-deaf and un-funny it is to joke about millions of people dying, you have to wonder what the heck was Jimmy Kimmel thinking when he linked BTS to COVID," one user posted to X. "Because there is no universe in which likening human beings to COVID is funny."

Frequent awards show host Jimmy Kimmel became a popular hosting choice, as he loved to make controversial jokes during some of Hollywood's biggest nights. During the 2022 Emmy Awards, he performed a bit where he quasi-drunkenly laid at the feet of "Abbott Elementary" creator and star Quinta Brunson as she accepted her first Emmy for the series. He remained in that position on camera for her entire speech, even after she jokingly asked him to get up, prompting many angry viewers to share their distaste for the sketch-gone-wrong online.

Brunson appeared on "Jimmy Kimmel Live!" a few days later, where both addressed the incident. "The last thing I would ever want to do is upset you because I think so much of you," Kimmel apologized to Brunson during their interview. "I think you know that. I hope you know that." Brunson, in turn, affirmed that she didn't take offense from the bit. "I was wrapped up in the moment and just having a good time, I don't know. I didn't see any of [the bit]." Despite the on-air kiss and make up, Brunson still got the last laugh by crashing Kimmel's monologue as a tongue-in-cheek comeback.

Jimmy Kimmel has never been one to shy away from a fight, particularly with fellow famous figures. Kimmel went for the proverbial jugular of NFL quarterback Aaron Rodgers, who insinuated in a January 2024 interview on "The Pat McAfee Show" that Kimmel was a listed associate of convicted sex offender Jeffrey Epstein. Kimmel not only published a brutal rebuff of the claims on his X, threatening legal action against Rodgers, but he also tackled the controversy head-on during an episode of "Jimmy Kimmel Live!" "Aaron Rodgers is too arrogant to know how ignorant he is," Kimmel said in the clip. "They let him host 'Jeopardy' for two weeks. Now he knows everything."

According to Kimmel, Rodgers's comments were retaliatory and stemmed from an earlier "JKL!" episode where the host questioned the quarterback's theories about the Epstein list and reported UFO sightings. "When I do get something wrong, which happens on rare occasions, you know what I do? I apologize for it," Kimmel continued. "Which is what Aaron Rodgers should do. Which is what a decent person would do. But I bet he won't." While the two haven't publicly squashed their beef, speculation continues over the pair's next tête-à-tête.

One of Jimmy Kimmel's biggest and most prolonged feuds is with former president Donald Trump. Over the years, both parties have publicly called the other out, from the online barracks of X to Hollywood's biggest stage at the Academy Awards. In March 2024, Kimmel even read Trump's real-time "review" of the Oscars, which Kimmel was hosting. "Thank you for watching. I'm surprised you're still [up]. Isn't it past your jail time?" the comedian quipped back during the live broadcast (via Sky News Australia).

This isn't the first time that Kimmel has utilized his platform to send shots at the political figure. Even before he became the U.S. president, Kimmel has continually pummeled Trump in the press. "One of the most fun parts of my job is knowing that [Trump] hates being made fun of and making fun of him, and everyone once in a while he reminds us that he hates it" Kimmel once told CNN, but that hatred wouldn't stop him from interviewing Trump again. "There are a lot of questions I would like to ask him and I would like to get actual answers."