Jimmy Kimmel has long been one of television’s most recognizable and beloved faces. As the host of Jimmy Kimmel Live and one of the few personalities to have helmed the Oscars multiple times, he’s carved out a distinctive legacy in the world of entertainment. Many fans expected him to once again take the stage at the Dolby Theatre for the 2024 Academy Awards, but that moment didn’t come to pass.

Reflecting on his return to the Oscars stage while speaking with the Los Angeles Times, Kimmel admitted, “I did not think I would ever do it again. I did two of them, and they went well — something crazy happened at one of them with a story I’ll have for the rest of my life. I know how much work goes into them, so I thought, ‘Yeah, I don’t necessarily want to do this ever again.’” Despite the intense preparation and long hours, he found himself saying yes once more.

When Jimmy Kimmel Live premiered in 2003, Kimmel was a newcomer in a competitive late-night field. Over the years, however, he steadily became a household name, now holding the title of America’s longest-running current late-night talk show host.

But recently, the question of whether Kimmel is contemplating stepping away has surfaced. During an episode of Strike Force Five—the podcast he co-hosted with fellow late-night personalities during the writers’ strike—Kimmel revealed he had seriously considered walking away from his show. Yet, it was the unexpected hiatus caused by the strike that reignited his passion for hosting.

“It’s hard to yearn for it when you’re doing it,” he shared with the Los Angeles Times. “Wednesday night, I was very tired and I had all these scripts to go through — I had to revise and rewrite all these pitch ideas for the Oscars — and I was literally nodding off onto my computer. In those moments, I think, ‘I cannot wait until my contract is over.’ But then, I take the summer off or I go on strike, and you start going, ‘Yeah, I miss the fun stuff.’”

Kimmel candidly added, “I think this is my final contract. I hate to even say it, because everyone’s laughing at me now — each time I think that, and then it turns out to be not the case. I still have a little more than two years left on my contract, and that seems pretty good. That seems like enough.”

When asked what he envisions for his future self, Kimmel painted a whimsical picture: “He is very accomplished. He speaks Italian, he plays the harmonica beautifully.” With a chuckle, he continued, “He is an expert fly-fisherman. He does all these different things that I know I’m not actually going to do. He’s drawn some graphic novels that were very well-received. He’s very busy — it’s funny, whenever I think of what I’m going to do when I stop working, it all involves more work.”

While nothing is officially decided yet, it’s clear that Jimmy Kimmel’s next chapter, whether filled with fly-fishing or writing graphic novels, will be just as vibrant—and likely just as busy—as the career he’s built over the last two decades.