Jimmy Kimmel has rarely shied away from making jokes about controversial public figures. It is, therefore, no wonder that the comedian, who found himself in some serious beef with President Donald Trump for his style of comedy, often cracks jokes involving P Diddy, who was convicted on charges including sex trafficking and racketeering.
On the March 12 episode of ‘Jimmy Kimmel Live!,’ the comedian started his monologue with the Oscars and how the weather was going to be quite hot during that time. Talking to his sidekick and co-host, Guillermo Rodriguez, Kimmel said, “It’s gonna be hot on Sunday, Guillermo, you’re gonna be on the red carpet, on Sunday.”
Guillermo replied affirmatively to this and added that he would be carrying a lot of water and tequila. At this point, Kimmel found an opportunity to insert Diddy into the joke, saying that to ensure Guillermo was well taken care of at the Oscars, he should opt for a ‘butler’ like the one who worked for Diddy.
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Referring to Diddy’s umbrella-holding assistant Fonzworth, Kimmel asked, “Remember that butler Diddy used to have? That guy who held the umbrella over [Diddy’s] head? We need to get you one of those.”
It should be noted here that this is not the first time that Kimmel has cracked a joke at Diddy’s expense. When Diddy was in the midst of his sex trafficking trial before he was convicted in October 2025, he said that the courtroom proceedings were “crazy.”
However, the comedian then added that the sketches of Diddy inside the courtroom appeared even stranger. Then, jokingly, Kimmel said, “Why did we settle on sketch as the official courtroom art? When I get locked up, I want to be sculpted.”
From this point, Kimmel pivoted to Diddy as he said that artists should not be “making sketches of Diddy” and added that “they should be oil paintings.” He then gave a little pause before he added “specifically” as the audience started laughing mid-joke.
The setting up of the punchline was enough for Kimmel’s viewers to know where it was going, as those who are even remotely familiar with the whole Diddy controversy would know what kind of oil Kimmel was referring to.
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Kimmel himself broke into laughter as he saw the audience guess the joke even before he could finish it. Highlighting the same, he said, “It’s not often that the entire audience predicts the punchline of a joke. I don’t know if that’s good or bad, but I’m glad you had fun!”
Given Kimmel’s current stance on Diddy, it is important to note that he was not always this brutal to the rapper and in a resurfaced 2018 interview, he had even joked that Diddy would be a better President than Trump, as he told him, “You would be a Boy Scout by comparison.” At that time, Kimmel had claimed that “almost anybody would be doing a better job” and also added that he would even be happy to serve as Diddy’s running mate.
However, since Diddy’s criminal convictions started, Kimmel’s stance towards him has taken a sharp turn, and he now regularly makes jokes at the rapper’s expense. Diddy is currently serving his sentence at the Federal Correctional Institution at Fort Dix, New Jersey and is reportedly planning to throw a massive celebration party once he is out.
