During the 96th Academy Awards, Donald Trump criticized Jimmy Kimmel's performance on his social media platform, Truth Social. Despite being advised not to respond, the late-night host, known for his show segment 'Mean Tweets' where celebrities read hurtful comments about themselves on X (former Twitter), reacted to the former president's comments by saying, "Thank you, President Trump. Thank you for watching. I'm surprised you're still up... isn't past your jail time?" This was a reference to a potential sentence that could send Trump to prison as a result of 91 federal and state felony charges against him.

There had been back and forth between the two for some time. In 2023, Kimmel revealed that he'd received a letter from Trump's organization, demanding that he retract a statement he'd made about the performance of the former president's platform. The comedian replied on the air, saying: "... in fairness, Truth Social isn't a colossal failure, it's only an abysmal failure."