Here's Why Jimmy Kimmel Mocked Don Jr.’s ‘Drag Queen’ GF Kimberly Guilfoyle

On Monday, Jimmy Kimmel, host of the late-night talk show took a shot at Kimberly Guilfoyle's speech at the Florida Republican party's 'victory dinner.' Guilfoyle is now engaged to Donald Trump Jr., son of Republican candidate and ex-president Donald Trump. In her speech, Guilfoyle said that the 'act three' of the Trump campaign was the 'art of the comeback'. Aside from alluding to his 1997 book of the same name, it was also a reference to the fact that this was Trump's third run for office, after 2016 and 2020.

As reported by The Daily Beast, Kimmel teased Guilfoyle by saying, "The art of the what?" on his program. He further went on to add, "Y’know, these people, they hate drag queen story hour… No problem with that." Nevertheless, Kimmel has always disliked Donald Jr., so calling out his fiancée seemed like it wouldn't be too far-fetched. Kimmel also recently chastised Donald Jr. for encouraging his father to pick JD Vance as his running partner. As reported by HuffPost, Kimmel stated, "Another good move, dumbass. If Trump loses this election, he’s gonna sue his son to take the ‘junior’ away."

Furthermore, last year, Kimmel mocked Donald Jr. when he testified in a $250 million fraud case against the Trump family company filed by the New York attorney general. The former president's son testified about fake paperwork about the financial situation of the Trump Organization, a real estate corporation. As cameras gathered in the courtroom, Donald Jr. at the time made a funny joke about regretting not wearing makeup. However, Kimmel did not think his quips were humorous.

As reported by OK! Magazine, Kimmel remarked at the time, "The fraud-igal son was being grilled as part of the $250 million case against their business." He further said, "Here’s the thing about Don Jr. What he lacks in intelligence, he also lacks in charisma." Kimmel said that Eric and Don Jr. would testify in the civil fraud trial 'and then Trump will claim he's never met either one of them.' The talk show host proceeded, "There’s even some worry Don Jr could be tried as an adult in this one," as the crowd burst out laughing.

Nevertheless, Aside from Donald Jr., Kimmel has also consistently mocked the previous president. Not long ago, Kimmel made fun of the full debate that took place between Donald and Kamala Harris. As reported by The Wrap, Kimmel stated, "It was like watching the Lorax debate the Grinch tonight. Usually when Donald Trump gets a spanking like this from a woman it’s with a Forbes Magazine. Kamala was pushing his buttons like a 12-year-old playing Fortnite."

The comedian also brought up the last debate (with Joe Biden) as an example and stated, "Oh, this was a much better debate than the last debate. This is like ‘The Lion King’ when Simba came back to avenge Mufasa." According to Kimmel, while preparing for the debate, Trump's advisers reportedly told him to be 'happy Trump' rather than 'mean, bully Trump' and to keep his attention on the issues. Kimmel continued, "Of course, he didn’t listen to any of that at all. But who are we kidding? This election isn’t about the issues. I mean, Dick Cheney isn’t voting for Kamala Harris because he agrees with her on the issues. He’s voting for her because there’s a rhinoceros charging, and she has the tranquilizer gun."