Jelly Roll returned as guest host of 'Jimmy Kimmel Live' for the second summer in a row on Monday night, wearing a suit and tie for the first time ever. He joked about his 300-pound weight loss, saying, 'That means I’ve lost an entire Donald Trump,' referencing the former president's approximate weight. The country singer reflected on his transformation, noting he had never worn a suit to the Grammys, court, or his father's funeral, but felt he looked 'all right' in his new attire.

His appearance highlighted both his personal health journey and his growing presence in late-night television. The segment blended humor with sincerity, showcasing Jelly Roll’s charisma and relatability as a host. Other late-night highlights from the night included John Oliver’s deep dive into subscription models on 'Last Week Tonight' and a preview of Stevie Nicks as the upcoming musical guest on 'Jimmy Kimmel Live'.