Times Jimmy Kimmel Has Made His Hatred For Trump Crystal Clear

For years, Jimmy Kimmel has relentlessly roasted Donald Trump on "Jimmy Kimmel Live!" His monologues about the man in the MAGA hat mostly have a political slant now, but he was joking about Trump long before he ran for president.

In 2021, Kimmel treated his viewers to a throwback clip of his first-ever Trump joke. It was from 2004, the halcyon days when Trump wasn't headlining insurrections, moaning about stolen elections, or fine-tuning his political sleight of hand. "It's so cold in New York, Donald Trump's combover broke off," Kimmel joked. As Trump became more political, Kimmel's material became more brutal. Amid his 2015 presidential bid, Trump had to cancel an appearance on "Jimmy Kimmel Live!" When he broke the news to his audience, Kimmel quipped (via Variety), "We're giving everyone in our audience a basketball dipped in cologne — so you can fully experience what it would have been like if he was here." Trump rescheduled, and Kimmel criticized his planned Muslim ban to his face. "Isn't it un-American and wrong to discriminate against people based on their religion?" he asked.

By 2023, Kimmel was celebrating Trump's indictment for charges related to paying Stormy Daniels hush money. "It's very, very funny," he said on his show. "Of all the things he's done, the one that bit Trump in the a** was a round of post-golf putter butter with the star of 'SexBots: Programmed for Pleasure.'" But when he talks Trump, Kimmel isn't always playing for laughs.

Times he has stopped joking when discussing Donald Trump

When he shames Donald Trump for his worst behavior, Jimmy Kimmel quits clowning around. During a 2017 episode of "Jimmy Kimmel Live!," he got emotional while telling his audience that his newborn son had undergone open-heart surgery. He then called Trump out for trying to cut billions of dollars in medical funding that would have impacted young patients like his baby boy. That same year, he made an impassioned plea to Trump voters. While begging them to admit to themselves that voting for "The Apprentice" host was a big-league blunder, Kimmel said, "He is a total disaster. He screws up royally every day." He also adopted a serious tone while discussing Trump's reaction to the widespread protests against police brutality and racial injustice that swept the nation in 2020. After denouncing Trump's tweet about shooting looters, Kimmel stated, "Enough is enough. We've got to vote this guy out already."

In 2023, Rolling Stone reported that Kimmel's material about Trump had rattled the billionaire so much during his presidency that he tried to use the power of his office to put a stop to it. Upon learning that White House officials had reached out to Disney about forcing him to lighten up on Trump, Kimmel said on his show, "This is a blatant abuse of power." He added that it was "especially hypocritical coming from someone who claims to be the biggest anti-censorship defender of free speech."

His clapbacks to Donald Trump's attacks on his show

Donald Trump was still willing to appear on "Jimmy Kimmel Live!" in 2016. Perhaps this is because there was the promise of a bedtime story from Kimmel, who read to him from a Trump-themed picturebook. But eventually, Trump seemed to realize that he was the butt of a lot of Kimmel's jokes. In Trumpworld, attacking someone's ratings is one of the worst possible insults. So when he went on a tweet-rant against late-night hosts in May 2020, he called Kimmel the "wacko 'last-placer'" behind Stephen Colbert and Jimmy Fallon. "Happy Cinco de Mayo Mr. President! Thanks for the shout-out — now get back to work royally f**king everything up!" Kimmel tweeted in response. On his show, Kimmel also advised Trump that his tweet would have been better spent offering his condolences to those who lost loved ones during the early weeks of the pandemic.

By 2022, Trump had taken his furious thumbs over to Truth Social. On "Jimmy Kimmel Live!," Kimmel shared a screengrab of a Trump "truth" saying that the three aforementioned late-night hosts "have very little talent." Kimmel clapped back, "That's the same thing Stormy Daniels said about him, except instead of 'talent' she said 'penis.'"

Kimmel fired back at Trump again one month later in response to the former president's claim that his show was toast. He quipped, "Our show is so dead he's gonna bury it next to his ex-wife at one of his golf courses." Yikes.

He loves annoying Donald Trump during the Oscars

If Jimmy Kimmel is hosting the Academy Awards, he's gonna mock Donald Trump in front of Hollywood's crème de la crème. In 2018, he cracked a joke about Trump tweeting from the toilet. Trump later hopped on X to write, "Lowest rated Oscars in HISTORY. Problem is, we don't have Stars anymore — except your President (just kidding, of course)!" Kimmel had the perfect retort. "Thanks, lowest-rated President in HISTORY," he shot back. (Gallup polling proved this true of the first year of Trump's presidency.) On his show, Kimmel boasted about his clapback getting double the amount of likes as Trump's tweet.

Kimmel insulted his nemesis and the Oscars after Trump issued a statement about the host-free 2021 show being lackluster and low-rated. "Donald Trump basically is the Oscars: old, bloated, completely self-involved, and obsessed with gold," he quipped on "Jimmy Kimmel Live!." Despite that dig, he was invited to host the Oscars again in 2024. Trump complained about Kimmel on Truth Social before that show ended, so the host read Trump's message aloud to the delighted crowd. He then addressed Trump: "Thank you for watching. I'm surprised you're still [up]. Isn't it past your jail time?" Kimmel later told CNN, "One of the most fun parts of my job is knowing that [Trump] hates being made fun and making fun of him." He added that it's even better when Trump reacts.

Jimmy Kimmel refused to tone down his Trump taunting

There are quite a few stars who hate talking politics, but Jimmy Kimmel isn't one of them. Some American citizens also have a "shut up and sing" mentality when it comes to celebrities — they want to keep Hollywood and politics separate. During a 2018 "Good Morning America" interview, Kimmel argued that this simply isn't a possibility anymore. When Americans decided to elect a reality show star as president, the two became inextricably entwined. You'd think the entertainment biz would want to follow suit by flavoring its programming with politics. However, Kimmel almost quit his show because his ABC bosses wanted him to be less political. On the "Naked Lunch" podcast, he recalled what he told the network: "I'm not going to do that. So if you want somebody else to host the show, then that's fine."

Kimmel knows his ratings would likely be higher if he took the Trump taunting down a few notches. According to the former host of "The Man Show," he actually used to have a robust Republican fanbase. "I have lost half of my fans — maybe more than that," he shared. Kimmel also explained why he's so passionate about shining a spotlight on the transgressions of Trump and other politicians. "I love this country, too. ... When I see somebody coming in and ruining it, I'm going to say something about it."

Why he would interview Donald Trump again

During one of his final interviews with Donald Trump, Jimmy Kimmel got the real estate mogul to confess to using the alias Barron when making real estate deals. And if Kimmel got his wish, he'd put his Trump-whispering talent to use again. In 2017, Kimmel told "Good Morning America" he believed he could actually get Trump to change his political views on air if they were to chat again. "I think he needs to be surrounded by better people," he said. But when Kimmel returned to the morning show a year later, his goal was less ambitious; he just wanted to grill Trump about his political transformation. "I'd be curious why he's changed his opinion on so many important things," he stated. In 2004, Trump told CNN his views were more closely aligned with the Democratic Party. He also used to be pro-choice, but thanks to his Supreme Court picks, Roe v. Wade was overturned.

In 2024, Kimmel told CNN he was still willing to interview Trump, despite their ongoing feud. He noted that Trump usually sticks to speaking with outlets that support him, adding, "I would like to get actual answers." From the sounds of it, he probably wouldn't let Trump walk away from their interview looking good. "I just cannot believe that anyone thinks it would be a good idea to put him back in the White House," he marveled.