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Jelly Roll on Jimmy Kimmel Live
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The gist
Jelly Roll guest-hosted 'Jimmy Kimmel Live' and joked about Trump's weight and Freedom 250 antics. The country singer's monologue surprised fans and marked his second year filling in for Kimmel.
Background
Jelly Roll, a country singer known for hits like 'Save Me' and 'Son of a Sinner,' is guest-hosting 'Jimmy Kimmel Live' for the week of August 24-28, 2026, as part of the show's summer guest-host lineup. He previously guest-hosted in 2025. During his Monday night monologue, he took multiple jabs at President Donald Trump, referencing Trump's weight gain and his appearance at the Freedom 250 Grand Prix, which drew surprise from viewers.
How it unfolded
- Aug 24, 2026Jelly Roll guest-hosts 'Jimmy Kimmel Live' for the first of four nights, wearing a suit and tie for the first time ever. In his monologue, he jokes about Trump's weight gain and the Freedom 250 Grand Prix.
- Aug 25, 2026Media outlets report on Jelly Roll's monologue, with TheWrap noting fans were 'very confused' and Rolling Stone highlighting his weight loss joke about losing 'an entire Donald Trump.'
- Aug 26, 2026 -28, 2026Jelly Roll continues guest-hosting through Friday, with scheduled guests including Nathan Fillion, Leslie Mann, and Bert Kreischer.
Who’s saying what
- Public
- One fan said, 'I'm very confused right now,' reflecting surprise at Jelly Roll's political jabs.
- Media
- TheWrap described the monologue as 'stunning' the audience with multiple jabs at Trump.