Twenty years later, and Jimmy Kimmel has no signs of stopping.
In fact, the primetime episode brought back the very same guests who appeared during the premiere on Jan. 26, 2003—including George Clooney, Snoop Dogg and Chris Martin. The trio joined Jimmy to reminisce on their favorite moments from their appearances in the time since.
Michelle Obama was also on-hand for the 20th anniversary special, leading a star-studded video segment where she paid tribute to the longtime host. "Thank you for your humor, your grace, your energy, your positivity," the former First Lady shared. "I love you, keep up the great work."
Jimmy also got the seal of approval from a pair of TV legends in their own right—comedian Carol Burnett and Oprah Winfrey.
In her message, Burnett pulled out her signature ear tug and sent a warm message his way. "Twenty years, wow. That's wonderful," she said. "I would just like to say, you are permanently terrific."
As for Winfrey? She reflected on her own experience with her long-running talk show by sharing some sage advice with the 2023 Oscars host: keep moving forward. "I know there's no way you thought this was gonna go on for 20 years, I understand how that happens," Winfrey quipped. "And before you know it, it's gonna be 25. So, congratulations and keep going."
Jimmy's longtime pal Jennifer Aniston echoed Winfrey's praise, adding, "I would please like 20 more years, because I don't want you to ever leave my television set cause you bring so much joy to myself and to the world."
Ben Affleck also popped up with a love note, sharing, "Jimmy, you are nothing if not an enormous talent and, to this day, my only friend who has written an entire song about f--king me."
Perhaps the funniest message, however, came from Julia Louis-Dreyfus, whose video was celebrating a different milestone altogether. "I say this with friendship and love in my heart—well, you don't look 20. I'm wondering if you have a thyroid issue or something? Anyway, I'm going to email you a couple names of doctors, I'm sure it's easily addressed with some medication," she joked. "Happy birthday."
Of course, it wouldn't be a JKL bit if it didn't end with his rival Matt Damon, whose "rivalry" with Jimmy has been a staple on the late-night show for almost as long as it's been on-air. "Congratulations, Jimmy Fallon. One of the most talented and also one of the kindest people—" he began before being interrupted and corrected on his mistake. Damon then ended the video with boos and a middle finger.
Fans can expect to see Jimmy for at least three more years, as the show has been renewed through season 23. He told E! News, "I just agreed to stay on for another few years, so I'm gonna be around for a while, God willing."
Tune into Jimmy Kimmel Live!, weeknights on ABC.