Jimmy Kimmel's Sly Trump Joke At The 2026 Oscars Sends Aide Into An Embarrassing Meltdown
In his late-night TV career, Jimmy Kimmel has brutally slammed the Trump family on numerous occasions. And, when he took a turn at the podium during the 2026 Oscars, to announce the winner of best documentary feature, the outspoken comedian couldn't resist taking a shot at them once again. After praising several documentaries that take on hard-hitting topics, Kimmel dismissed Melania Trump's brutally-reviewed, eponymous film by quipping, "There are also documentaries where you walk around the White House trying on shoes," (via CP24).
The late-night host also referenced President Donald Trump indirectly as he opened the envelope, proclaiming, "Oh man, is he going to be mad that his wife wasn't nominated for this," (via X, formerly known as Twitter). Instead, it was White House Communications Director Steven Cheung who got triggered. Cheung took to X to bash Kimmel for his jokes, calling the celebrated TV personality "a classless hack who is self-projecting his depression and sadness onto others," adding, "He lives a pathetic existence." Donald actually didn't melt down about Melania's exclusion from the Oscars.
Jimmy Kimmel (Mr. Blackface) is a classless hack who is self-projecting his depression and sadness onto others. He lives a pathetic existence where nobody— not even his family— enjoys his miserable company. The only people giving him any attention are Hollywood Elites. BUH-BYE! https://t.co/cynWTtdidH
— Steven Cheung (@StevenCheung47) March 16, 2026
Besides, her documentary came out too late in 2025 for consideration, so she still has a chance for next year's ceremony. Notably, this isn't the first time Cheung has had beef with Kimmel. "Jimmy Kimmel is a no-talent loser," the White House staffer asserted to Entertainment Weekly when his show was briefly paused in September 2025. However, while that Kimmel drama spotlighted Donald's fragile ego, in this more recent instance, Cheung just embarrassed himself. As one X user reasoned, "Incredible that someone who allegedly speaks for the most powerful man in the world spent their afternoon writing a Yelp review about Jimmy Kimmel's home life."
Steven Cheung can't seem to stop insulting people
In his X tirade about Jimmy Kimmel, Steven Cheung also felt compelled to bring up the late-night host's early career, referring to the comedian as "Mr. Blackface." Kimmel already publicly owned up to this mistake back in 2020. In fact, in his apology, Kimmel included a preemptive response to Cheung's recent behavior. "It is frustrating that these thoughtless moments have become a weapon used by some to diminish my criticisms of social and other injustices," the Emmy winner explained in his official statement at the time (via 6ABC). Kimmel is not the only comedian Cheung has targeted either.
"Stephen Colbert is a sad and pathetic excuse for a human being," the White House communications director proclaimed on X just days before he attacked Kimmel. "Nobody likes a loser who killed the legacy of The Late Show." Cheung's account is filled with similar insults and tirades across other professions, but he targets female journalists in particular. The MAGA loyalist has clashed with CBS News' Margaret Brennan and Sky News' Yalda Hakim, among many others. Cheung's relentless invectives often backfire, with commenters calling him out for his behavior.
"Facts don't care about name-calling, Steven," admonished one such X user. Another turned Cheung's comments back on him, retorting, "'Sad and pathetic' guess you're the expert on that, steve." Then again, it's possible that White House workplace culture has made it second nature for Cheung to hop on social media to make hurtful comments. He's been part of the president's political career from the very beginning, and Donald Trump is known for insulting people right in front of him.