The 75-minute "Conan" finale, more than twice as long as the usual half-hour version of the show, also featured highlight reels and amusing appearances by Will Ferrell and Homer Simpson. It capped a 28-year late-night run for O'Brien that started in 1993 with NBC's "Late Night" in 1993 and moved briefly to NBC's "The Tonight" Show" before settling in for the last 11 years on TBS.
A tuxedoed Black, the sole guest in studio, walked onto the stage of Los Angeles' Largo theater set with a cane and a Velcro boot. It wasn't a joke: He'd sprained his ankle a day earlier pre-taping a finale musical number that was supposed to result in the "School of Rock" star suffering a fake injury.
"The funniest part is we had an ambulance there" with attendants, O'Brien told the audience. "I'm yelling at these two guys like, 'We've got to help him.' And they were like, 'No, we're actors.' They said, 'But we just need an ACE bandage,' and I said, 'Well, get one out of the ambulance.' And they said, 'No, it's a fake ambulance.' So, these two guys dressed as ambulance drivers with an ambulance drove to CVS and bought ACE bandages. It's the stupidest (expletive) thing I've ever seen."
Black, who had an MRI Thursday that revealed a bad sprain, added: "I was so bummed because I wanted to be the best guest all time for your final episode. And it's sad. I am literally the lamest."
While Black couldn't dance, the Tenacious D singer more than made up for it with a rousing rendition of "My Way" titled "Cones' Way," his nickname for O'Brien and featuring O'Brien-centric lyrics, including: "He's tall/He's really pale/He has red hair/Like Howdy Doody/But more, much more than this/He did it Cones' Way."
Homer Simpson and O'Brien, who was a writer for "The Simpsons" before becoming a late-night host, appeared in an animated opening segment in which Homer was an H.R. rep conducting an exit interview.
When O'Brien said he thought Homer worked in a nuclear plant, the cartoon character responded, "Over the years, I've had hundreds of jobs. At one point, I was even a monorail conductor," he said, referring to the famed "Simpsons" episode written by O'Brien, "Marge vs. the Monorail." "What a stupid idea that was!"
Ferrell, a guest on O'Brien's final episodes of "Late Night" and "The Tonight Show," said he couldn't miss the "Conan" closer, appearing via Zoom from Boston where he's filming. However, Ferrell said he's finding the tributes exhausting, so he asked to pre-tape goodbyes for Conan's future series, including his next actual venture: an HBO Max variety show.
Ferrell fake-saluted the "six episodes" of that show, jokingly suggesting a quick cancellation. Then the comedic actor went on an even higher flight of fancy, congratulating Conan on phony future series: an Al Jazeera talk show; a Delta Airlines in-flight talk show called "Wheels Up!"; and a reality competition series, "Celebrity Room-Temperature Oyster-Eating Contest."
Thursday's episode was the culmination of a run of favorite O'Brien guests in the final two weeks, including Bill Hader, Seth Rogen and Dana Carvey, along with a special pranking by Paul Rudd. Andy Richter, O'Brien's dryly amusing sidekick going all the way back to "Late Night," was there at the end, too.
For the last segment, O'Brien, 58, sitting on a stool in much the same way Johnny Carson did on his "Tonight Show" finale, thanked the show's writers and producers, with special shoutouts to Richter, "Saturday Night Live" executive producer Lorne Michaels, "Friends" alum Lisa Kudrow and O'Brien's wife, Liza Powel O'Brien.
Of Richter, he said: "When I found Andy Richter, he was one of the funniest people that I ever met. I never said to Andy, 'You can't get the laugh. I've got to get the laugh.' The rule was always, if you think of the funniest thing, just say it, and that'll get us out. And he did it a hundred thousand times. He's a brilliant man. And I love him forever," he said as the two hugged.
Of Michaels, who picked former "SNL" writer O'Brien for "Late Night," he said: "When I was chosen to replace David Letterman, people thought it was a crazy, stupid idea. I had no experience. I really shouldn't have had the job. Lorne said, 'I think that guy.' And NBC said, 'The writer with the weird hair?"' And he was like, 'Trust me, he's got something.' Lorne put his credibility on the line. He changed my life and I’ll owe him forever."
Of Kudrow, whom he met doing improv in 1985, he said: "I immediately sized her up as one of the coolest, most talented people I'd ever meet and a lovely person. When I started to go through the possibility that I might get this job ... Lisa Kudrow had more faith in me than I did. She said, 'You have to do it. You're like the only one that can do it.' I thought she was nuts, but I wouldn't be doing this job if it wasn't for Lisa Kudrow."
Of his wife, the mother of their two children, he said: "The most amazing thing that happened to me over the 28 years of various shows – we were shooting a remote and I saw this woman who was an advertising executive. You can see me kind of fall in love with her on camera. (Marrying her) was the best decision I ever made in my life, including late night."
O'Brien closed explaining how he's spent his adult life "pursuing this strange, phantom intersection between smart and stupid" which, when attained, is "magic."
"I am so grateful to all my staff and the fans who have joined me in this crazy and seemingly pointless pursuit, to do things that are kind of stupid but have something smart in there somewhere," he said, offering some final advice: "Try and do what you love with people you love. If you can manage that, it's the definition of heaven on Earth."
Contributing: Gary Levin, Hannah Yasharoff
This article originally appeared on USA TODAY: Conan O'Brien ends TBS late-night show with injured Jack Black's help