Jimmy Kimmel Brutally Roasted The Trump Family After Barron's High School Graduation

For the Trump family, Barron Trump's graduation was made even more memorable, as it brought Donald Trump and Melania Trump together during a tumultuous time. The former president was granted a day off from his trial to attend his youngest son's graduation on May 17. He took to Truth Social to post about the occasion, "Going to Barron's High School Graduation. Great student, wonderful boy! Very exciting!" Donald wrote (via ABC News). Unfortunately for the Trumps, Jimmy Kimmel used this post as fodder for roasting Donald and the family. 

During his monologue on "Jimmy Kimmel Live" for May 20, Kimmel ripped Donald for his seemingly detached social media post about Barron's graduation. "It's like what you would say to your schnauzer after it graduated obedience school," he joked to the audience. Kimmel followed that by firing off a joke aimed at Melania. "54-year-old Melania spent the ceremony wedged between her 77-year-old husband and her 80-year-old dad, dressed like a gondolier in mourning," he said. The comedian added that Donald had a disinterested look on his face during the event. "[S]ame face he made when Eric was born," Kimmel said. He also clowned Barron for his graduating sash. "Trump let Barron borrow one of his giant red fat guy ties," the host observed.

"Jimmy Kimmel Live" fans flooded the show's YouTube page with praise for the biting commentary. Kimmel has become an expert at roasting Trump, and he did not hold back when Trump came after him online earlier in the year.

Jimmy Kimmel made his hatred for Donald Trump crystal clear when he ripped the former president during the 2024 Oscars. The host called an audible and read a Truth Social post from Trump during the ceremony. "Thank you for watching. I'm surprised you're still up. Isn't it past jail time?" Kimmel said at the Oscars on March 10, while alluding to Trump's multiple trials, per CBS News.

That joke did not go unnoticed by Trump, who went on the offensive against the late night host the following month. "Stupid Jimmy Kimmel, who still hasn't recovered from his horrendous performance ... the WORST HOST EVER OF THE ONCE VAUNTED ACADEMY AWARDS!" the former president wrote on Truth Social on April 17. In his strongly-worded post, Trump also mistook Kimmel for Al Pacino's bizarre reading of the best picture winner. "In fairness to our former President, many stable geniuses confuse me with Al Pacino," Kimmel wrote on X, formerly Twitter, in response to Trump's post. 

Later that night, Kimmel continued to take shots at the Republican presidential candidate. During the April 17 monologue on "Jimmy Kimmel Live," the comedian jabbed at Trump still obsessing over the Oscars joke. Kimmel also said it could be difficult for Trump to catch him hosting the 2025 Oscars. "Maybe you can watch on the TV in the rec room at Riker's with all the guys," he joked. Kimmel did not let up, and kept ripping Trump during his criminal trial.

Not only was Donald Trump's hush money trial with Stormy Daniels great fodder for Jimmy Kimmel's monologues, but "Jimmy Kimmel Live" was even mentioned during the court case. In 2018, Kimmel had booked Daniels as a guest, and the host asked her questions about her alleged affair with the then-president. That led to texts between Trump and Daniels' lawyers, which were presented in the criminal trial. The development which elated the comedian. "We are part of the official record of the people versus Donald Trump," Kimmel said during his monologue on May 2. Kimmel wanted to be more involved in the case. "Why was I not asked to testify? It's outrageous! I'm going to start suing people!" he said mockingly. Kimmel took another shot at the former president, adding, "I think I can keep Trump awake during the trial."

The following week, Kimmel was mentioned during the court case once again. When Daniels took the stand to testify, she was asked about her 2018 appearance on "Jimmy Kimmel Live." "Somehow, I've become the Kato Kaelin of this trial," Kimmel boasted, as a reference to the key witness in the O.J. Simpson trial.

Kimmel also had more jokes in the holster for Trump's wife. The late night host also brought up (via The Daily Beast) how Trump had given Daniels the pet name of "honey bunch" during their tryst, "Interestingly, it's also a term Melania [Trump] would use at Mar-a-Lago. As in, 'Honey, bunch of FBI agents out there!'"