Times Jimmy Kimmel Brutally Slammed The Trump Family

Known for his critical stance on former President Donald Trump, Comedian Jimmy Kimmel has found additional ammunition in the New York civil fraud trial involving the Trump family. On November 13, 2023, Kimmel celebrated his 56th birthday with a standup routine targeting the Trumps, whom he labeled a "very dumb crime family." His jokes revolved around the Trump family's alleged strategy of consistently denying knowledge of the fraudulent practices for which they were found liable.

Kimmel also dubbed them the "Gambozos," merging the infamous Gambino crime family and the slang "bozo." His routine humorously featured an interview skit, with talk show personality Guillermo Rodriguez as the interviewer. When Rodriguez asked what appeared to be an AI-generated Trump to identify his two sons, he responded, "These are people that are very, very disturbed." This isn't nearly the first time Jimmy Kimmel has aimed at the Trump family. Over his decades-long career, the talk show host has frequently criticized various Trump family members. Here are five of Jimmy Kimmel's most brutal digs at the Trump family.

Jimmy Kimmel has frequently roasted former President Donald Trump on his show "Jimmy Kimmel Live," even labeling him a "fearless misleader" on March 19, 2020. On April 12, 2023, he called Trump "a profoundly stupid person," adding, "That mental competency test he keeps bragging about? That's something the average seven-year-old could pass." Kimmel also compared Trump to Hitler after Trump described his enemies as "vermin" on November 15, 2023. He noted a key difference between both men: "Hitler was married to a woman who loved him."

The famed comedian also targeted Trump's explanation of his dinner with Nick Fuentes, which stirred quite a debate online on November 28, 2022. Trump claimed he'd never met Fuentes or knew about him, prompting Kimmel to quip, "That's the same thing he says whenever Eric comes over to eat." Jimmy Kimmel's November 2, 2023 standup also took a jab at Trump's parenting style, remarking that Trump's absence at his sons' testimonies is the "Trump family version of not showing up for their school play."

Melania Trump, often portrayed as the long-suffering matriarch of the Trump family, has not been spared by Jimmy Kimmel's comedic jabs. A notable instance followed a November 10, 2023, report by The Washington Post. The article featured an interview with Melania's former advisor, Stephanie Winston Wolkoff, who revealed that Melania delayed moving to the White House until a new toilet was installed. In response, Kimmel joked that she probably wanted to ensure it was "large enough to flush herself down."

On Melania's 52nd birthday in 2020, Kimmel couldn't resist a playful dig, joking that Trump sent her a birthday email beginning with, "Dear supporter." Kimmel also played on words after learning that Melania was discovered by photographer Stane Jerko, commenting that she "eventually married a much bigger Jerko." The comedian has consistently poked fun at the supposed signs of Donald Trump and Melania's split. On October 26, 2020, he made a tongue-in-cheek comment about her alleged body double, suggesting that such a smile would have been a reality for Melania had she married someone else.

Donald Trump Jr. has slammed celebs and angered the internet on multiple occasions, so it's no surprise that Jimmy Kimmel's comedic critiques have extended to him. One memorable roast came when Trump Jr.'s comment during the New York Civil suit, "I should have worn makeup," went viral. Kimmel's witty retort on November 1, 2023, was, "What he lacks in intelligence, he also lacks in charisma." He even dubbed Trump Jr. "the fraudigal son."

Kimmel didn't miss a beat when mocking Trump Jr.'s "embarrassing" description of his father as a "real estate artist," quipping, "Yeah, he's an artist. He's Vincent van Gogh-ing to jail." This is hardly Kimmel's first go at Donald Trump Jr. Back in 2017, amidst the Russian email scandal, Kimmel likened Donald Trump Jr. to an incompetent office staff: "Donald Jr. is like the guy at work who opens the obviously fake document, and now everyone in the office has a virus on their computer." 

Jimmy Kimmel's playful roasting of the Trump family inevitably includes former First Daughter Ivanka Trump. In 2017, when Ivanka received an office in the West Wing, Kimmel remarked that she would bring her "20 years of foreign and domestic policy experience that she gained selling sandals to Nordstrom" (via Business Insider). He also humorously suggested that Ivanka was positioned close to her father to prevent him from deploying nuclear weapons (via Yahoo Finance).

Kimmel didn't shy away from commenting on how Ivanka Trump almost lost her job as a White House advisor. He sourced material from the book, "Confidence Man" by Maggie Haberman, which stated that Trump planned to fire Ivanka and her husband, Jared Kushner, via a tweet. Kimmel jested that Ivanka was saved by a KFC chicken thrown across the room to distract her father. On February 15, 2023, when Donald Trump expressed a desire to reinstate firing squads, Kimmel's response was expectedly sharp-witted: "If Trump executes all the criminals, who's going to send him a Father's Day card? Friends of Ivanka?"

Jimmy Kimmel's comedic lens has frequently focused on Eric Trump, the second son and third child of the Trump family. In 2019, Kimmel poked fun at Eric's attempt to put a positive spin on the crowd's reaction to Donald Trump during a UFC event in New York City. Amidst loud booing, minor cheers, and chants of "lock him up," Eric tweeted optimistically about the crowd's response, even looking forward to the 2020 election to "embarras" the naysayers, complete with a misspelling.

Kimmel couldn't resist commenting on the tweet, saying, "Nothing sums up Eric Trump like misspelling the word 'embarrass.' How does he misspell a word he's seen on every birthday card since he was five years old?" On February 3, 2021, Kimmel quipped on Trump's relationship with his kids after Eric's numerous declarations of being proud of his father. The comedian quipped, "I think he's hoping that if he says he's proud of him enough times, the father of America might say it back to him one day." Eric's testimony in the 2023 Trump family civil fraud case also caught Kimmel's attention. When Eric claimed his expertise was in construction, not accounting, Kimmel dubbed him "Tweedle-even-dumber," adding, "He's a construction guy in the same way the guy in the 'Village People' is a construction guy."