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Jimmy Kimmel Mocks Diddy’s Shockingly ‘Crazy’ Courtroom Sketches

May 23, 2025
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Jimmy Kimmel Mocks Diddy’s Shockingly ‘Crazy’ Courtroom Sketches
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Jimmy Kimmel is still fascinated by the ongoing trial of Sean “Diddy” Combs, but he’s even more interested in Diddy’s courtroom sketches.

“The Diddy trial in New York, it’s pretty crazy,” Kimmel said in his Thursday monologue. “And even the courtroom sketches are crazy, because this is supposed to be Sean Combs…”

He showed one of the courtroom sketches, drawn by artist Christine Cornell during his May 14 hearing.

“It looks more like an evil Luther Vandross,” Kimmel joked. “Here’s another one from a different artist…”

Sean
Sean “Diddy” Combs listens as Mylah Morales testifies at Combs’ sex trafficking trial in New York City, New York, U.S., May 22, 2025 in this courtroom sketch. Jane Rosenberg/REUTERS

He showed another famous sketch, this one drawn by artist Jane Rosenberg from Reuters.

“This one looks like Diddy knows how bad the drawing’s going to be and is like, ‘Really? You’re going to draw me looking like Danny Glover saw a ghost?’”

Kimmel joked further, “Why did we settle on sketch as the official courtroom art? When I get locked up, I want to be sculpted. I would like a courtroom sculpture artist to depict me.”

He added, “These drawings look so little like Diddy, I keep getting confused and thinking Uncle Ben is being tried for sex crimes.”

“They shouldn’t be making sketches of Diddy. They should be oil paintings, specifically,” Kimmel said, in a joke that garnered some gasps from the audience, followed by applause.

“It’s not often that the entire audience predicts the punchline of a joke,” Kimmel mused. “I don’t know if that’s good or bad, but I’m glad you had fun.”

Kimmel mused about Diddy’s portraits, “I wonder if it’s the same artist who did Trump when he was on trial, because he didn’t like those at all. He looked like he melted in those.”

It turns out Kimmel was correct: Rosenberg, the artist behind the second picture he showed, was also behind some of Trump’s most famous courtroom pictures.

Trump had reportedly remarked, upon seeing one of Rosenberg’s portraits of him, “That’s me? I think I need to lose some weight.”

The post Jimmy Kimmel Mocks Diddy’s Shockingly ‘Crazy’ Courtroom Sketches appeared first on The Daily Beast.

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