Hollywood’s Biggest Night Briefly Felt Like a Late-Night Comedy Show When Jimmy Kimmel Stepped Onto the Stage at the Academy Awards and Slipped in a Biting Joke About a Documentary Tied to a Former First Lady.

At the Oscars, first lady Melania Trump came under fire from Jimmy Kimmel, who described her most recent documentary as a movie about “trying on shoes” at the White House.

On Sunday at the Academy Awards, Kimmel gave the Best Documentary Short Film award while highlighting the importance of documentaries. He pointed out that since they expose injustice or teach important lessons, films are frequently produced under extreme personal danger.

In a shot at Trump, whose documentary Melania was released earlier this year, Kimmel remarked, “There are also documentaries where you walk around the White House trying on shoes.”

 

Jimmy Kimmel takes swipe at 'Melania' documentary at Oscars

 

Kimmel also acknowledged that not everywhere accepts the value of free speech, saying those places are “North Korea and CBS,” in a dig at the network for allegedly censoring late night host Stephen Colbert.

The documentary, which debuted earlier this year and later began streaming on Amazon Prime Video, has been the subject of sustained mockery from Kimmel on Jimmy Kimmel Live!.

The film, directed by Brett Ratner, follows the former first lady in the period surrounding Donald’s return to office and has drawn criticism from reviewers who described it as light on substance and heavily focused on image, fashion and behind-the-scenes moments.

Kimmel also announced the winner for best feature documentary and said President Donald Trump would be mad that Melania’s documentary wasn’t nominated for the award.

US First Lady Melania Trump looks on as US President Donald Trump (out of frame) speaks to members of the military and their families at Fort Bragg, North Carolina on February 13, 2026. Trump will meet on Friday with the special forces soldiers who captured Venezuelan leader Nicolas Maduro in a deadly raid in Caracas in January.
Jimmy Kimmel Thanks Donald Trump After Winning Critics ...

Kimmel has repeatedly labeled the project a “vanity documentary” and used it as a punchline in multiple monologues, including jokes about its reported budget, box office performance and critical reception.

 

Critics Choice Awards 2026: Jimmy Kimmel takes aim at Donald Trump in  acceptance speech - Entertainment News | The Financial Express

One clip from the documentary that has drawn particular attention — and laughter from Kimmel — shows Melania appearing disengaged during a phone call with her husband on the night Congress certified the 2024 election results. In the exchange, Melania tells Donald she did not watch the coverage live and would “see it on the news,” a moment Kimmel described on his show as “one of the funniest conversations I’ve ever heard,” adding that it “almost makes me feel a little bad for him.”

 

Her documentary has been defended in conservative media circles, with some commentators praising its audience reception and fashion-focused approach, even as mainstream critics have been far less enthusiastic.

The Oscars moment also revived a familiar dynamic between Hollywood and Trump-era politics, especially at a ceremony that has increasingly become a venue for pointed cultural commentary. Kimmel has never shied away from political humor, and his antagonistic relationship with Donald dates back years, including previous Oscars broadcasts. During the 2024 ceremony, Kimmel famously read a social media post from Trump attacking him mid-show, responding live from the stage and drawing widespread attention.

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