Here Are 10 of Jimmy Kimmel’s Most Popular and Funny Digs at Former President Donald Trump

These Are 10 of Jimmy Kimmel's Funniest Comments Regarding Ex-President Donald Trump

Since the start of Donald Trump's serious bid for the 2016 presidential election, late-night talk shows have found a lot of comedic material. Among the hosts, Jimmy Kimmel stands out as a popular critic, fearlessly coming up with the most biting humor against Trump, despite once hosting him as a guest on his show. All the major late-night hosts extended invitations to the former President, only to distance themselves from him soon after. Notably, as reported by PEOPLE, Kimmel disclosed his decision to exit Jimmy Kimmel Live! when network executives asked for a reduction in jokes targeting Trump. So, clearly, there is no love lost between the two. With that in mind, here is a glimpse at some of Kimmel's most memorable Trump-themed jokes that became popular for late-night television.

1. When Kimmel Poked Fun at Truth Social

The current financial struggles faced by Truth Social—Trump's attempt at a Twitter-like platform—became great fodder for the comedian, who took no time to comment on the dire situation. Kimmel mockingly said that Truth Social has lost so much money that they might have to start calling it Twitter. His humorous take was sparked by a security filing that showcased Truth Social's huge loss this year, following a profitable stint in 2022. As reported by The Wrap, Kimmel also humorously dubbed it as Trump's 'number one most successful company yet.' "Even Melania Trump hasn't posted in 2 months. Melania Trump's whereabouts are currently unknown," Kimmel further said.

2. Kimmel Joking About Trump Lying About His Weight

Kimmel directed criticism towards Trump for allegedly stating his weight as 215 pounds during his booking at Atlanta's Fulton County Jail in August. "If I were the judge in the case he has going in New York right now, I'd start the trial by saying, 'Look, we're gonna get to the fraud thing, but, first, pop up on this scale, big fella,'" Kimmel said, reported The Wrap. Additionally, the comedian highlighted Trump's claim of weighing 30 pounds lighter than what he did during his presidency. This difference also led Kimmel to speculate that the former President was either lying or attempting weight loss through unusual means, humorously suggesting that Trump was 'frying his chicken in Ozempic' (a weight-loss drug). 

3. When Kimmel Called Trump a ‘Fragile Little Snowflake'

At one point, the ex-president felt so uneasy about Kimmel's jokes that his administration apparently attempted to pressure Disney into censoring Jimmy Kimmel Live! Understandably, Kimmel seized the opportunity and gleefully used this on his show, creating a comedic spectacle out of the situation. “You’d think the guy who fathered Eric and Don Jr. would know how to handle jokes, but I guess not,” he said. Kimmel proceeded to delve into an extensive list, recounting nearly every nickname he had ever employed for Trump on his show. “What a fragile little snowflake. What a blowhard. He’s a blowhard and a snowflake. He's a blowflake,” Kimmel joked. 

4. Kimmel Was Celebrating Trump's Indictment

For years, Kimmel has maintained a ruthless stance against the former President, foreseeing an event like this one. We all know now that Trump has been impeached twice and indicted four times, but back when news first broke out about Trump facing an official indictment related to the 'hush money' controversy involving former adult film star Stormy Daniels, Kimmel took no time to slam the real estate mogul. Kimmel joined the group of TV hosts providing commentary, bringing a playful tone as he announced Trump as the first former U.S. President to face indictment, reported HuffPost. “The ‘J’ in ‘Donald J. Trump’ now stands for ‘Jail,’” Kimmel said to his live audience. He further added, "It’s historic, and it’s funny. It’s very, very funny." 

5. When Kimmel Mentioned Trump Had Another Motive Behind His Presidential Run

Trump declared his candidacy for the 2024 presidential race, setting the stage for another high-stakes political story. After his notable defeats in the last presidential campaign, Trump became the subject of Kimmel's jests, who humorously suggested that the real estate mogul's renewed bid for office might secretly be to secure a record as the first individual in American history to lose the popular vote in three consecutive presidential elections. In 2016, Trump won the electoral college but actually faced a deficit of nearly 3 million popular votes, followed by a wider margin of over 7 million votes in 2020. Adding to the comedic commentary, Kimmel highlighted the recent trend of prominent Republicans distancing themselves from Trump post-midterm elections, signaling a shift in the political landscape.

6. Trump Shares a Connection with 'Stormy DeSantis,' said Kimmel

During his first live show, Kimmel continued his humorous jabs aimed at Trump. Kimmel wasted no time diving into Trump's remarks where he said that if the GOP achieved success, he [Trump] should receive full credit, yet in case of failure, he'd refuse to accept any responsibility. Additionally, Kimmel acknowledged Governor Ron DeSantis' victory in the Florida re-election, shedding light on DeSantis as a noteworthy figure in Trump's political orbit. Kimmel also labeled DeSantis as Trump's potential nemesis in the forthcoming elections. "Uncle Scam says if he did run, ‘I’ll tell you things about him, that won’t be very flattering.' I know more about him than anybody other than perhaps his wife, who’s running his campaign," Kimmel said. He further said, “My god, did Donald Trump have sex with stormy DeSantis," as per OK! Magazine.

7. Kimmel Made a Bold Remark About 'Adult-Sized Genitalia'

Kimmel sharply criticized Trump following the ex-president's focus on Kimmel's genitalia. Pointing at Trump, he said, “So proud of himself, like a tubby, orange brat knocking over sand castles at the beach. And I like that he says we have ‘very little talent.’ You know, that’s the same thing Stormy Daniels said about him—except, instead of ‘talent’ she said ‘penis.’” Kimmel continued, “But if anyone knows talent, it’s Donald Trump." Moreover, Kimmel took a moment to confront Trump's remarks regarding late-night ratings, delivering a message representing his fellow late-night hosts. “Jimmy, Stephen, Seth, and I, we’ve been on for a total of 58 seasons and counting. Your presidency got canceled after one,” he said, as per Yahoo! News. 

8. Kimmel Delivered a Hilarious Monologue at the Oscars

As the host of the Oscars, Kimmel targeted Trump repeatedly throughout the evening, engaging in mockery and even daringly provoking the former President with two tweets from the stage. During his opening monologue, the late-night host humorously quipped that the Academy Awards had a global audience spanning 'in more than 225 countries that now hate us'. He said, "I want to say thank you to President Trump. Remember last year when it seemed the Oscars were racist? That's gone, thanks to him." Furthermore, Kimmel humorously suggested that Trump would likely take to Twitter to comment on each of the Oscar winners' acceptance speeches.

9. When Kimmel and Hair Stylists Indulged in a Funny Conversation About Trump's Hair

Kimmel went on a quest, interviewing hairstylists across New York City, seeking insight into the mystery behind Trump's hair. Renowned stylists came in, adding a touch of humor by poking fun at Trump's infamous hairdo, notably taking digs at one time when Trump was boarding Air Force One in early 2018. Kimmel quipped that as Trump jetted off to Mar-a-Lago for the weekend, his hair seemed eager to head there separately. One stylist likened Trump's hair to the back side of a dog, while another humorously compared it to an ostrich's back side. Others labeled it as a bad weave as well. Amid the jests, a few stylists also shared constructive thoughts on how they might approach the hair situation.

10. Kimmel Recalled the First Joke He Made About Donald Trump

Kimmel also recalled the very first joke he shared with the public regarding Trump. This notable recollection coincided with the 18th-anniversary celebration of Kimmel's namesake show. The comedian instructed his staff to prepare a video clip, intending to exhibit to the audience the moment he humorously addressed the former President's hair. "You know, they say it's going to be the coldest week in two decades on the East Coast this week. It's supposed to be minus-8 over the next couple of days. It's so cold in New York, Donald Trump's combover broke off," he said. In addition, Kimmel also remarked that they spent the entire day rehearsing that particular line, prompting loud laughter from the audience.