Black, who O’Brien requested be his final guest, came onstage with a cane and walking boot after rolling his ankle after actually hurting himself while rehearsing a bit where he was going to pretend to injure himself on the show.
“Let me start off by saying I love you Conan. I’ve always loved you, since the year 2000,” Black sang, a nod to O’Brien’s Late Night-era prediction sketches. “I mean, I loved you before that, but that was the first time we met in person, my first-ever talk show appearance, and I was scared as hell. I was petrified, I’d never been in front of a late-night audience before, and you were so smart and funny and kind, it was the best way to enter the late-night television world, and I will always feel a special connection with you and worship you.”
After praising O’Brien’s sidekick Andy Richter, Black explained how he’d manage to injure himself while pretending to injure himself during rehearsals for a big musical number. Despite his inability to perform that big musical number, the Tenacious D singer still serenaded O’Brien with an altered version of “My Way” that paid tribute to “Conan’s Way.”
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Prior to leaving his talk show, an animated, Simpsons-style version of O’Brien sat down with Homer Simpson to conduct a TBS exit interview (before his career in late-night, O’Brien served as a writer on the beloved cartoon for two seasons). After O’Brien asked why he was handling human resources at TBS, Homer cracked, “Over the years, I’ve had hundreds of jobs. At one point, I was even a monorail conductor. What a stupid idea that was!” A fitting nod to one of O’Brien’s most famous episodes, Season Four’s “Marge vs. the Monorail.”
Finally, Will Ferrell — who appeared twice earlier in the week to send off O’Brien — returned yet again via Zoom to bid farewell one more time. The actor previously appeared as a guest on O’Brien’s final episodes of both Late Night and The Tonight Show, so they kept the tradition alive with Conan.