Jimmy Kimmel Would Stop If He Could

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Jimmy Kimmel jokes that he’s getting a lot of offers of support from people who can’t actually help him. He was speaking in April while dealing with his third public disagreement with Donald Trump in under a year, and many friends were reaching out. It started when Trump, after CBS cancelled Stephen Colbert’s show, predicted Kimmel would be next, claiming he was less talented than Colbert. Shortly after, ABC briefly suspended Kimmel’s show after he made a joke about Trump’s reaction to a tragic event, only to reinstate it a week later, prompting Trump to threaten legal action. This time, Trump is angry about a joke Kimmel made during a mock White House Correspondents’ Dinner, where he described Melania Trump as looking “like an expectant widow.” Just two nights later, someone tried to attack the actual White House Correspondents’ Dinner. Almost immediately, conservative commentators and social media influencers began suggesting Kimmel’s joke was responsible. By Monday, Trump had publicly called for Kimmel to be fired on his social media platform.

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Inside the JKL! offices, the atmosphere was surprisingly calm. Jimmy Kimmel was casually walking around in socks, snacking on frozen raspberries, and jokingly apologizing that the afternoon would be dull – spent watching him write his monologue. Though the show isn’t live anymore, taping was delayed an hour to give the team extra preparation time. Kimmel and writers Josh Halloway, Greg Martin, and Nick DiLorenzo were quietly typing into a shared Google document, occasionally stepping out for more snacks. Every now and then, someone would share a thought aloud. “After watching everything unfold on Saturday night, I wondered how they’d try to blame this on me,” Kimmel remarked. He communicated with the writers via Slack, quickly approving or rejecting their ideas with thumbs-up and thumbs-down emojis. Once a draft was ready, he’d munch on ice and rewrite it to sound natural and conversational, like a regular guy chatting at a bar. He explained that he aims for a tone that’s “assertive but reasonable,” adding, “I’m typically inclined to fight back, and in that way, Donald Trump and I aren’t so different.”

Kimmel and his show, JKL!, share a history of pushing boundaries. Throughout his career, he’s often spoken or acted impulsively, dealing with the fallout afterward. Early on, his comedy was frequently immature and intentionally provocative. The show had a rocky start – a bar set up for the audience had to be removed after an audience member became ill during the very first episode. He was known for controversial interview questions and jokes, like asking a member of t.A.T.u. to sit on his lap or digitally altering a photo of Carnie Wilson for a joke about her Playboy spread. Getting female guests proved difficult, and an appearance by Jennifer Garner was considered a significant achievement. For years, JKL! struggled in the ratings, consistently trailing Jay Leno’s Tonight Show. However, around the ten-year mark, ratings began to improve, exceeding 2 million viewers. Today, despite the overall decline in live television viewership, JKL! regularly outperforms Jimmy Fallon’s Tonight Show, with numbers continuing to rise from 2025 to 2026.

Jimmy Kimmel has matured since he first started performing and is now willing to admit when he’s gone too far and offer an apology. He views apologizing not as a sign of weakness, but as a core principle, drawing a parallel to his Catholic faith. Over the years, he’s apologized for several instances, including using blackface to impersonate Oprah Winfrey and Karl Malone in the 1990s and early 2000s, and for a joke in 2004 where he suggested Detroit Pistons fans might riot if their team won. He’s even apologized for jokes he didn’t fully regret, like a 2013 segment where he playfully engaged with children making outrageous statements – including one suggesting violence towards China. This segment sparked protests and led to apologies from both Kimmel and ABC. He says he took the blame to protect the Disney company, but now genuinely regrets the incident.

Jimmy Kimmel has reached a point where he won’t apologize for things he doesn’t believe were wrong. He told Disney that he needs to be able to do the show his way, without constant oversight. This time, after another disagreement about Trump, Disney simply told him to address the issue and move on. On his show, Kimmel admitted the shooting was deeply upsetting, but pointed out his long-standing support for stricter gun laws, and argued no one could honestly think he was encouraging violence. He sarcastically suggested that if anyone believes a joke he made days before the event had any impact, they should investigate a psychic. The segment then cut to White House press secretary Karoline Leavitt, who, on the red carpet before the White House Correspondents’ Dinner, predicted Trump’s speech would be combative, saying ‘There will be some shots fired tonight.’

Following his opening monologue, Jimmy Kimmel spends a few minutes chatting with the audience before starting the guest interviews. Though he tries to seem engaged, he appears preoccupied, and the conversation veers into a lengthy discussion about converting Celsius to Fahrenheit and a joke about fewer Canadians attending tapings due to perceived animosity. While his audience expects him to be the outspoken critic of Trump, Kimmel seems more interested in a detailed conversation with a woman who works at a laser eye surgery center about the pros and cons of different procedures. I complimented him on the show after taping, and he simply replied, “Thank you. It’s…you know, it’s a weird show.” He then headed to his office to change out of his suit and go home, feeling ambivalent about his job – sometimes he enjoys it, and sometimes he doesn’t.

Late-night television is facing a difficult period. Stephen Colbert finished his run hosting The Late Show on May 21st, with some suggesting the White House played a role, though CBS cited financial reasons. The show itself, after 33 years, is being replaced by a less controversial comedy program hosted by Byron Allen. NBC has reduced funding for Seth Meyers’s Late Night, and Jimmy Fallon’s Tonight Show has seen declining viewership. Other hosts known for their political commentary have moved to smaller platforms like The Daily Show on Comedy Central and Last Week Tonight With John Oliver on HBO. Jimmy Kimmel remains the most visible late-night host still broadcasting to a live audience, and he continues to challenge those in power.

For the past ten years, late-night hosts like Kimmel, Colbert, Meyers, Oliver, and Fallon have been figuring out how to respond to viewers eager for criticism of Donald Trump. Colbert’s show used playful disapproval, subtly judging Trump from a position of superiority. Meyers took a different approach with his “A Closer Look” segments, offering commentary from a more casual, less authoritative stance – he often wore casual clothes and stayed seated at his desk, injecting a quirky, intellectual humor into his Trump critiques. Oliver consistently and thoroughly condemned Trump on his show, but always within longer, in-depth explorations of various topics. Fallon, on The Tonight Show, generally avoided directly criticizing Trump. A joke during a recent appearance with all five hosts highlighted their shared demographic – middle-aged white men making news-based jokes – and ended with Fallon feigning ignorance about current events, prompting Oliver and Meyers to reassure him that everything is fine.

Today’s late-night hosts have a much friendlier relationship than hosts like Jay Leno and Conan O’Brien had in the past. They stay in touch through a group chat, get together for meals, and even co-hosted a podcast during the 2023 writers’ strike. The recent decision to end The Late Show with Stephen Colbert isn’t just about television; it’s also tied to politics. Many believe Paramount canceled the show as a way to appease the Trump administration and make a merger with Skydance Media easier. This followed a $16 million settlement Paramount paid Trump over coverage on 60 Minutes, and as rumors circulated about Paramount potentially buying Warner Bros. Discovery, John Oliver publicly criticized Paramount on his show, describing it as a company willing to compromise its values for profit.

After The Late Show ended, Jimmy Kimmel admitted he felt disheartened, saying it made him think about his own future. He compared it to Billy Joel’s song “Allentown,” which is about broken promises and the decline of American industry. Despite claims that late-night TV is losing relevance, Kimmel argues that viewership is actually quite strong when you combine online views with traditional TV ratings. He believes the format isn’t failing naturally, but is being deliberately undermined. He points to Stephen Colbert’s contract with CBS as an example. In 2023, CBS reportedly tried to get Colbert to sign a five-year deal, but he chose three years. Then, just two years into that contract, CBS cancelled the show, claiming it was losing $40 million a year. Kimmel questions this explanation, asking why the network would offer a five-year deal if the show was already losing so much money. He believes the reported losses are fabricated.

Jimmy Kimmel acknowledges his show isn’t making as much money as those hosted by Johnny Carson or Jay Leno used to, but ABC has assured him JKL! is currently profitable. However, Disney recently renewed his contract for only one year—a shorter term than the usual three years—reflecting the current unstable environment. He explains, “Everything is so tumultuous,” and a one-year extension “seemed to make sense.” His current contract ends in May 2027, and he’s unsure if he’ll sign another one or announce his retirement. He’s given a lot of thought to how he might end the show, emphasizing his sense of responsibility. He believes going out with a dramatic farewell would be attention-grabbing, but ultimately feels it would be a selfish decision.

Jimmy Kimmel remains close to the people he grew up with – those from his childhood in Brooklyn and later Las Vegas – and many of them continue to be important in his life and career. After years of being fired from various radio jobs, he quickly began hiring his friends and family once he achieved financial security. One of his first hires was his cousin, Sal Iacono, known as Cousin Sal, who joined him on the Comedy Central show Win Ben Stein’s Money in 1997. Iacono, a former law student who hadn’t passed the bar, lived in Kimmel’s office for a year and became a key writer for many of Kimmel’s future projects. Another close collaborator was Adam Carolla, a friend and creative partner Kimmel met while working at the L.A. radio station KROQ. Together, they created the intentionally silly series The Man Show in 1999 and the prank-call puppet show Crank Yankers in 2002.

When Lloyd Braun at ABC offered Jimmy Kimmel a late-night hosting job, Adam Carolla and Damon Iacono continued with JKL!. Kimmel made sure his childhood friend, Cleto Escobedo III, was hired as the bandleader, and also that Escobedo’s father joined the band. Besides Cousin Sal, Kimmel has employed five other family members on JKL!, including his wife, Molly McNearney, who is an executive producer and head writer. Hiring family is unusual in the entertainment industry, where it’s typically something people apologize for, rather than highlight. Kimmel is straightforward about it, saying he runs the show like a family-owned restaurant, relying on the people he trusts most. He believes his faith in his family’s humor is key to the show’s success, stating that if he finds someone funny, the audience will too, and so far, he’s been proven right.

Carolla believes Kimmel is generous, but that generosity has created a deeply loyal team that ultimately benefits him – a rising tide lifts all boats, as they say. Carolla thinks this loyalty is the main reason Kimmel hesitates to retire. He suggests Kimmel feels trapped by his responsibility to his staff, wondering what would happen to long-term employees, like someone who’s worked with him for four years and just started a family, if he were to leave.

Since his days on The Man Show, Adam Carolla has become a vocal political commentator, identifying as a libertarian and often praising Donald Trump. He’s also publicly disagreed with vaccine mandates and the Black Lives Matter movement. Despite their differing political views, Jimmy Kimmel and Carolla remain close friends, much like Kimmel stays connected with family members he doesn’t agree with politically. Kimmel explains, “I love Adam, and he loves me, and I’ve accepted that I can’t change his mind. Arguing with him wouldn’t help.” When asked about his willingness to criticize Trump, Kimmel clarifies, “Trump is different. I don’t love him, and I don’t hate him. I actually feel sorry for him – he clearly didn’t receive much affection growing up.” Kimmel’s jokes about Trump on JKL! often portray Trump as a schoolyard bully who disrupts everyone else’s lives. Kimmel doesn’t try to reason with Trump; instead, he responds with his own brand of playful aggression. According to writer Brendan McNearney, the show once tried to avoid mentioning Trump altogether. “We used to fill our monologues with lighthearted content,” McNearney remembers. “But those days are over.”

Trump appears bothered by Jimmy Kimmel because Kimmel isn’t afraid to directly engage with him in a playful, even critical way, unlike other late-night hosts. For example, in May, Kimmel joked about Trump ignoring rules, comparing it to him exceeding the weight limit on a golf cart. The monologue included a humorous sketch featuring “Trump’s Mysteriously Bruised Hand” – a bright orange hand resting on a pale belly next to spilled fried chicken. Kimmel still retains the playful, immature humor from earlier in his career. After years of being encouraged by ABC to appear more mature, he now directs that energy towards targeting Trump. He admits, “I feel like I’m exactly the same as when I was 10 years old,” suggesting he enjoys the playful confrontation.

Jimmy Kimmel enjoys playfully teasing people, especially those close to him. His show still relies heavily on pranks and stunts. For example, a recent segment featured his elderly Aunt Chippy accidentally getting into a self-driving Waymo car, and the family watched her panic as it drove off without a driver (“Oh my God! I want to get the fuck out of here!”). Kimmel also has a secret account on the Nextdoor app where he purposefully responds to neighborhood complaints in a deliberately insensitive way, then shares screenshots with his friends. He once responded to a woman complaining about stolen fanny packs for a bride and her friends, offering to sell some of his own. Kimmel explains that making people laugh for a living can sometimes take away from the simple joy of being funny.

Honestly, Jimmy Kimmel’s need to pull pranks is just constant and a little wild. I remember hearing about this thing he did back in 2012 where he took his wife’s phone and spammed the same hashtag – ‘#webejammin’ – on all her Instagram friends’ posts. It kicked off this whole prank war with the JKL! writers, and things just escalated. Like, someone actually glued a license plate holder to another writer’s car that said ‘I SHIT MY PANTS AT UNIVERSAL CITYWALK’! Even when the show was paused, he couldn’t stop. He designed a ‘missing chimp’ flyer using his daughter’s account, and then he and his kids went around the neighborhood posting them, even included a burner phone number just to listen to the voicemails – which were mostly people imitating chimp noises, apparently. John Mulaney put it perfectly: there’s no stopping this guy. It’s like watching Anton Chigurh from No Country for Old Men – even after a disaster, he’ll just keep going and find some new, slightly unhinged thing to do, like putting up those missing chimp posters.

Jimmy Kimmel’s love of pranks started when he was a kid growing up in Las Vegas with his friend, Escobedo. They were always getting into mischief, like playfully harassing people from his dad’s car and ordering so many fake pizzas that local restaurants stopped delivering to their street. Kimmel’s father recalls finding a drawing of a penis in the middle of an important meeting, along with a note from Jimmy hoping he’d enjoy it. While the surprise is part of what makes a prank fun, Kimmel says what he truly enjoys is seeing how predictably people react. He believes that even without the fame and platform he has now, people would still respond in the same way. Kimmel views this as a surprisingly human side of himself. He explains, “I love reactions. It’s the genuine, unfiltered responses that I find fascinating. I like seeing people in their natural settings, acting as they normally would.” He even enjoyed watching the reactions at the White House Correspondents’ Dinner after a security scare, because it revealed what people were really like when they let their guard down.

The evening after the show taping, Jimmy Kimmel had me over for dinner at his house in the Hollywood Hills. He has a barn connected to the house with a podcasting studio and a guest room he offers to friends—John Mulaney even stayed there for three weeks while going through his divorce. Kimmel made lasagna with homemade pasta and grilled zucchini in the backyard. He encouraged me to try a kumquat straight from his tree. He also prepared a simple salad of iceberg lettuce and tomatoes with a special red wine vinegar, and when he found out my husband enjoys cooking too, he insisted I take a bottle home. Later, worried the bottle might break during my flight, he meticulously packed it for me. He searched around on the floor behind a cabinet for the perfect plastic bag, then vacuum-sealed the bottle and put it in another Ziploc bag for extra protection. The next week, when I emailed him a quick question, he added a note apologizing if he’d made me check a bag because of all the packaging.

Those who know Jimmy Kimmel say he’s always been incredibly thoughtful, going to great lengths to give personalized gifts and experiences. He’s become even more sentimental as he’s gotten older. At 58, he embodies classic dad sensibilities, citing authors like Kurt Vonnegut, musicians like Bruce Springsteen, and television personalities like David Letterman (and James Taylor) as influences on his values. He’s currently in therapy and uses an Oura Ring to track his health. Even when hosting a guest, he meticulously checks the temperature of the food he serves – and was genuinely thrilled when his usually picky son agreed to try it.

Jimmy Kimmel is a very emotional person. Over the last ten years, he’s become well-known for openly crying on stage when talking about difficult personal experiences. As David Letterman puts it, even small things can make him tear up. Kimmel doesn’t seem to separate his feelings from what he shares with the audience. A particularly moving example was a monologue he gave a couple of months after being off-air, where he announced the death of his close friend and bandleader. He shared stories from their childhood and became emotional when he mentioned the street they grew up on. However, he received the most attention for a 2017 monologue about his newborn son, Billy, needing emergency heart surgery. Kimmel connected his family’s experience to the national conversation about healthcare, and his story led to politicians using the “Jimmy Kimmel test” – asking whether proposed healthcare laws would cover families facing similar situations and pre-existing conditions.

It might seem strange, but genuine honesty is a key part of Jimmy Kimmel’s comedic style. He admits he’s not a highly-educated person, but recognizes his own intelligence, and believes his sincerity is finally being noticed, especially given current events and the national climate. Kimmel’s political views aren’t based on a strict ideology; instead, they come from a gut feeling of what’s right and wrong. His opposition to Trump isn’t simply about principle; it’s also a personal response to something he finds deeply upsetting.

Jimmy Kimmel is at his best when he connects personally with a story, especially when he feels something is deeply wrong. However, this focus on personal experience can also highlight his shortcomings. Following George Floyd’s murder in 2020, Kimmel admitted he hadn’t fully understood white privilege, stating he was beginning to grasp the idea that white people aren’t judged based on their skin color. He later apologized for using blackface in past sketches, calling them embarrassing. But he also expressed frustration that these moments were being used to undermine his current criticisms of injustice, asserting he’s grown and matured significantly over the past two decades and that this is reflected in his work.

Early photos from the beginning of JKL! show Jimmy Kimmel looking completely exhausted. He was still recovering from a divorce from his first wife, Gina, and their children, Katie and Kevin, frequently slept in his office. Kimmel recalls a grueling schedule: waking up at 6 a.m. to take the kids to school and not finishing work until after 10:15 p.m. He describes those days as simply trying to survive, then improve, and finally thrive. He admits things are still challenging now, saying, “the waters are rough and the waves are very big.”

He’s considering ending his show. He previously discussed leaving six years ago, during Biden’s presidency, but wants to make the final decision himself. His producer, Erin Irwin, has noticed he’s been thinking about it for a while and would ideally like the show to run through the 2028 election, though she worries he doesn’t have the energy to continue that long. Kimmel is also concerned that Trump might exploit something he says on air to pressure ABC into canceling the show. He feels confident he could defend himself if challenged on past jokes, but acknowledges that eventually, he’s bound to say something that could cause problems, and he jokes about that inevitability.

I’ve been a huge fan of his work on JKL! for years, and like clockwork, he’s planning his summer break again, starting right after the NBA Finals on June 19th. It’s funny, I remember this time last year he was just finishing up talks about extending his contract. Usually, by now, those negotiations would be in full swing, but he recently said they haven’t even started yet! He seems a little unsure about what the network wants, but he’s staying positive, reminding everyone he still has a year left on his current deal, and he intends to honor that.

When I asked Jimmy Kimmel what he planned to do after his show, JKL!, ended, he showed me a sweatshirt he’d painted. It featured a scene from Swan Valley, Idaho, where he owns and runs a fishing lodge. He explained how completely focused he gets when he’s painting. “It takes over everything,” he said. “I lose track of time and find it hard to stop.” He misses having that kind of immersive experience with projects, something he enjoyed as a child. “I honestly don’t know what I’ll do professionally after the show,” he admitted. “More than anything, I want the freedom to do things I enjoy, like going fishing when the conditions are right.”

Despite knowing he’ll eventually retire, he finds it hard to picture the actual moment. His office is packed with memories – photos with Letterman and Carolla, a drawing of him hugging Howard Stern, and years’ worth of quirky gifts and awards from colleagues. Simply closing down the show feels like a huge task, especially when it comes to packing up all his belongings. He also worries about becoming overwhelmed with emotion, something he’s tried and failed to control. He’s attempted various methods – pinching himself, even briefly considering antidepressants – trying to mentally prepare himself with the thought, ‘This time I won’t fall apart.’ But he admits, ‘The moment I start speaking, I know I’ll lose it.’ He suspects this fear is a major reason he hasn’t retired yet, believing his final show will be incredibly emotional.

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2026-06-01 14:59