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‘Conan’ Finale: Guest Jack Black Shows Up Injured, While Conan O’Brien Celebrates the ‘Intersection of Smart and Stupid’

·12-min read

Conan O’Brien ended his 11-year run on TBS’ “Conan” by touting the “intersection between smart and stupid.” And that’s why, perhaps it was all too appropriate that final guest Jack Black wound up on stage wearing a walking boot for a sprained ankle — an injury he received while rehearsing a song and dance number he had planned for O’Brien’s finale.

The irony of the moment: As originally planned, Black was pre-taping a big musical number that involved a lot of physicality. As part of the bit, he was going to pretend to get injured — and as actors playing paramedics were to take him out on a gurney, he would hop up and run back to the theater.

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But then, “the crazy thing is, I actually injured myself, for real,” Black said. Adding to the irony, those actors playing paramedics were stationed in a prop ambulance — which had no actual medical equipment to help him out.

“Today I went and just to be safe I got an MRI and they were like, ‘it’s a real sprain, you got some damage there. You’re gonna have to take it easy, no dancing, no running, no physical craziness for a while,’” Black said. “I was so bummed because I wanted to be the best guest of all time for your final episode and instead I am literally the lamest!”

READ MORE: As Conan O’Brien Ends His Late-Night Show, Producer Jeff Ross Reflects on an Unprecedented 28-Year Run

O’Brien said he felt terrible — but also acknowledged that it felt fitting for the self-deprecating nature of his show. “When Carson, Letterman and all these legends go off the air everything is meticulous,” he said. “Of course, we would think of a bit with Jack where Jack pretends to get hurt and while shooting it, Jack gets hurt. We’re the only show in the history of the medium that would ever do that. It’s somehow fitting.”

Quipped sidekick Andy Richter: “Johnny would have had Jack shot!”

Andy Richter, Jack Black, Conan O’Brien - Credit: Conaco/TBS
Andy Richter, Jack Black, Conan O’Brien - Credit: Conaco/TBS

Conaco/TBS

Black still pulled through with a rousing musical tribute to O’Brien while wearing that boot. Black also reminded O’Brien that his first-ever talk show appearance was on “Late Night with Conan O’Brien.”

“I was scared as hell,” Black recalled. “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. And I have to say Andy is the most incredible sidekick of all. Razor sharp, off the top of your head. No one can ever replace you. I know that I said I wanted to replace you. Let me set the record straight, that was all bullshit. I’m not smart enough.”

Enjoy his number here:

Earlier in the expanded hour and 15 minutes episode, Will Ferrell appeared over Zoom from Boston, where he said he was “shooting a secret project” — and then joked that it was “Batman.”

“And guess what in this version Batman gives oral,” Ferrell quipped. “It’s graphic. Full frontal. Batman like you’ve never seen him before.”

Ferrell noted that he also appeared on O’Brien’s final “Late Night with Conan O’Brien” and last “Tonight Show” episode. “It’s fucking exhausting,” he said. “I love you Conan, but if you don’t mind, can I pretape a few goodbyes and you can use them when your next several shows flame out?”

O’Brien has a new show lined up for HBO Max next year, but Ferrell’s pre-tape isn’t optimistic: “Congratulations on an outstanding run on your HBO Max show. Six episodes isn’t a lot but you packed enough entertainment in them for eight episodes.” Ferrell also taped farewells for his eventual show on Al Jazeera, Delta in-flight talk show, unboxing videos on YouTube, MTV 3’s “Videos of People Dry Humping in Trucks,” and the reality competition show “Celebrity Room Temperature Oyster Eating Contest.”

“But then your show was tragically cut down in its primed by an explosive diarrhea outbreak,” Ferrell said. “Who could have predicted it? Everyone, apparently. Conan, I’ve seen the footage and it was horrifying. Variety called it ‘Sunday Muddy Sunday.’ Because instead of blood, it was diarrhea. It was so deadly. A lot of people died.”

The episode, taped at the Largo at the Coronet (“Conan’s” home during the pandemic), also included a roundup of guests over the years Martin Short, Zack Galifianakis, Nicole Byer, Andy Samberg and Lea Delaria. Another package featured O’Brien trying out jobs like a Mary Kay beauty consultant, commercial actor and modern dancer. And a “Conan Without Borders” package featured his trips to Cuba, South Korea, Armenia, Israel, Australia, Mexico, Ghana, Germany, Japan, Greenland and Italy.

“It’s been a great way for me to hide my money in banks all around the world,” O’Brien said.

Guests in the audience included O’Brien’s wife Liza, and his long-running assistant Sona Mouvsesian, who surprised the host by being there, even though she is about to give birth to twins.

“Conan” opened with a special clip produced by “The Simpsons” team, in which Homer Simpson gave O’Brien — famously, a former ‘Simpsons’ writer — an exit interview. (Watch below.)

“That gave me goosebumps,” O’Brien said. “That meant the world to me they went to all that trouble.”

O’Brien ended the episode with several thanks:

“First of all, I’m the beneficiary of literally hundreds and hundreds of really talented, amazing people. And then I’m just the nose cone of the rocket. And there’s so many people to thank. Eleven years ago, I made the decision to come to TBS. At the time, people really surprised that I did that. They didn’t think that would be the move. I did it for one reason: a guy named Steve Koonin came to me, and he’s one of the loveliest people I’ve ever met in show business. He’s what the Irish call a mensch. (We take words that we like!) Anyway, he came to me and he said, ‘I will protect you, I will let you and your people do whatever you want. I’ll never interfere and we’ll support you 100%.’ They did that. They did that in every single way. They never went back on their word. They were extraordinary. And lovely.

“The people at TBS were nothing short of remarkable. None of this would have happened. I’d have gone away a long time ago if it weren’t for them. So Steve Koonin, I thank you. David Levy, Kevin Reilly, Dave Wolkis, Sandra Dewey, Brett Weitz, Jen Cohen. Love you. Thank you all so much for making this happen. I want to thank my squad. They’ve been with me forever: Rick Rosen and Gavin Polone, they are the best at what they do and they take really good care of me.

“I’ve got to bring up the guy who I met back in 1993. I was paired with him to try this crazy thing. No one thought it would work. And he’s been my executive producer since then. And we are brothers from different mothers. Our executive producer, our hefe, Jeff Ross.

“Jack Black brought up something really important. In another era. a sidekick was someone who sat next to the host and laughed along and just sort of supported them. And they were great in their way, they all had their special skills. And when I found Andy Richter, he is one of the funniest people that I ever met. And I put him next to me and I never said to Andy, ‘give me room, 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 100,000 times. He’s a brilliant man. And I love him forever. Andy Richter.

“I started as a comedy writer, so I always took it as a point of pride. I always wanted to have the very best comedy writers and I did. Starting in 1993 until now. I cannot express how brilliant these people are. And I don’t often know that writers are appreciated as much as they should be. I know that there are awards for them, but they’re behind the scenes. You have no idea the courage of many of my writers. The ingenuity, the beauty of their minds, how they work, and they’re also really good people. I’ve been blessed with the best writing in television, in my opinion for 28 years.

“I’ve got a call out two in particular right now because they’re just amazing people who still have kept the show going all through the TBS years and that is Mr. Michael Sweeney. He’s amazing. And he’s always in the trenches, and he goes with me on all the travel shows, and we’ve been we’ve been having fights all over the world, it’s just absolutely absurd and half the time he’s wearing his pajamas. Someone else, Mr. Matt O’Brien, who I have to point out, he’s no relation to me at all. He’s just a brilliant writer in his own right. But I always tell people that he’s my uncle’s son, and we had to hire him. And so many interns think it’s true. And they don’t give him the respect he’s due and I think it’s the funniest thing in the world.

“There’s a guy on our show who never gets any recognition. I think he started with me way back in the early 90s as an intern, and he is the guy who travels the world with me. He’s the guy that makes things happen. When people try and shut us down and try and stop a shoot, he does some crazy thing that’s illegal. He gets shot in the leg but doesn’t say anything about it till later. He is the truest warrior I’ve ever met Jason Chillemi. A brilliant woman who is our line producer and makes everything happen. If she left us tomorrow, I would leave show business. And Jeff would leave. She just makes everything work. She’s genius. Sarah Federowicz.

“This is very hard for young people to understand. But in 1993 when I was chosen to replace David Letterman, people thought it was a batshit crazy, stupid idea. They didn’t know me the way you do. I had no experience. I really shouldn’t have had the job. One guy changed my life. Lorne Michaels at ‘Saturday Night Live’ said, ‘I think that guy’ and NBC said, ‘the writer with the weird hair?’ And he was like, ‘trust me, he’s got something.” And Lorne put his credibility on the line. I remember reading an article that said Lorne Michaels has taken like the biggest gamble of his career with this complete unknown for such a big job. Lorne saw something in me. I’d like to think he was right. And he changed my life and I owe him forever. He’s a great man.

“Quick shout out to Lisa Kudrow who I met right outside these doors in a little improv actors space. And in 1985, 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, which was I must repeat a completely insane idea. And nobody except Lorne thought it could work. Lisa Kudrow had more faith in me than I did. And she said, ‘You’ve got to do it, you have to do it. You’re like the only one that can do it.’ I thought she was nuts. But you wouldn’t know me if it wasn’t for Lisa Kudrow.”

After thanking his parents, siblings, wife and children, O’Brien ended with these parting words of wisdom:

“And now just close with this one thought I have devoted all of my adult life, all of it, to pursuing this strange phantom intersection between smart and stupid. And there’s a lot of people that believe the two cannot coexist. But God, I will tell you, it is something that I believe religiously. I think when smart and stupid come together, it’s very difficult. But if you can make it happen, I think it’s the most beautiful thing in the world. I am so grateful to all my staff and the fans in this country and around the world who have joined me in this really crazy and seemingly pointless pursuit to do things that are kind of stupid, but have something smart in there somewhere. And then there’s a little tiny sort of flicker of what is a kind of a magic. I think that’s what I believe. So my advice to anyone watching right now, and it’s not easy to do, but try. Try and do what you love with people you love. And if you can manage that it’s the definition of heaven on earth. I swear to God, it really is. So good night. Thank you very much.”

Watch his farewell here:

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