After nearly 30 years on the air as a late-night—beginning with Late Night and leading up to Conan with a memorably short-lived pitstop at The Tonight Show along the way—Conan O’Brien is getting ready to say goodbye. As the former SNL and The Simpsons writer barrels toward his June 24th finale, he’s gathering up some of his all-time favorite guests to help him bid adieu.
On Tuesday night, O’Brien’s TV career came full circle when he sat down with Sarah Silverman, one of his most frequent guests over the years and one of his earliest, too. As the two reminisced about the many times they’ve sat down together with cameras rolling over the past 28 years, O’Brien shared a photo of their very first interview from 1993—when Silverman was a 22-year-old comedian just getting her start, and O’Brien was a 30-year-old host still finding his way. Both comedically and sartorially speaking…
“Why was I dressed like Tom Jones?,” O’Brien asked sidekick Andy Richter—but also the universe in general. “What was that jacket? I’m dressed like The Riddler or something.”
The conversation took a surprisingly emotional turn as both host and guest, clearly moved, talked about what the other meant to their career. As Conan explained:
“I was 30 when you first came on the show. I had just turned 30 when we started doing the Late Night show [and] it takes a while to figure out who you are, comedically. And so, it’s not that you were trying to be someone else, it’s just that you’re trying to figure out how to be you on television.”
For her part, Silverman told O’Brien:
“I love your show so much. I do. I love it so much. I mean, the first time I ever was recognized on the street was from your show. Because you’d always have me on. I’ve been on your show for so many years. I grew up on your show. I honestly feel like my whole death reel could just be clips from your show [and] I’d be happy.”
O’Brien’s response? “I say aim higher.”
You can watch the full clip above.
