Stephen Colbert was delighted by the forthcoming cover of TIME magazine, which features a photograph of President Trump taken from an unflattering angle.
Trump himself complained about the photo on Truth Social, arguing that the picture might just be “the worst of all time.”
“He’s right,” Colbert said in his Tuesday monologue. “You got to hand it to him: it is.”
Colbert jokingly suggested some alternative AI-generated pictures that TIME could have used instead, including Trump “solving horse crimes,” where the president is dressed as a cowboy sheriff, or “the one where he has an extremely casual attitude towards highway safety,” where Trump is seen holding a guitar while riding a motorbike.
His last example—a real photograph—produced shocked applause from the audience.
“You want a flattering photo for the cover of TIME? How about this one?” the late-night host asked.
He showed a picture of Trump and convicted sex offender Jeffrey Epstein hanging out together in 1997.
Colbert has often ripped into Trump for his many apparent connections with Jeffrey Epstein, especially in light of Trump’s apparent heel turn on releasing the Epstein files in July 2025.
“Wait, hold on, what’s that pervert doing in there?” Colbert asked about the picture. “Take that pervert out.”
The photo was replaced with one where Trump, not Epstein, was removed.
Referring to Trump’s neck fat in the cover photo, featured prominently thanks to the camera’s low angle, Colbert joked, “Worst Georgia O’Keeffe ever.”
O’Keeffe was a 20th-century artist whose paintings of flowers were often compared to female genitalia, although O’Keeffe herself rejected that interpretation.
Colbert continued, “Of course, the president of the United States is far too busy hammering out the details of a deal to end a generational conflict in the Middle East to worry about how he looks on some biweekly magazine… you would think.”
Although Colbert mocked Trump’s meltdown over the photo, he admitted there was a lot for Trump to be upset about.
“There’s a lot going on there,” Colbert said. “It’s like one of those optical illusions where you can’t tell if it’s an old woman or a young ball sack.”
