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Injured Jack Black helps Conan O’Brien bid farewell to late night

Dimitrios Kambouris/Getty Images for Turner

Conan O’Brien‘s late-night TV run ended with an ironic twist — literally — as his final guest, Jack Black, entered the stage wearing a walking boot for a sprained ankle.

The injury, which apparently wasn’t a gag, happened while Black was taping a song and dance number for the show.  Ironically, the bit involved Black pretending to get injured.  Actors, dressed as paramedics, would then have carried him off on a gurney, only to have the actor-comedian hop off and run back to the theater.

“The crazy thing is, I actually injured myself, for real,” Black explained.  Adding insult to injury, the ambulance was also a prop, with no actual medical equipment on board.

Conan joked that it was only fitting that, “When [JohnnyCarson, [DavidLetterman and all these legends go off the air everything is meticulous,” he added. “Of course, we would think of a bit with Jack: Where Jack pretends to get hurt and while shooting it, Jack gets hurt.

Conan’s sidekick Andy Richter then quipped, “Johnny would have had Jack shot!”

Black still managed to turn in a rousing musical tribute to O’Brie,n called “Cone’s Way,” a parody of the Frank Sinatra classic “My Way.”

O’Brien, 58, ended on a more serious note, saying, “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…it’s very difficult.  But if you can make it happen, I think it’s the most beautiful thing in the world.

Will Ferrell also appeared on the show via Zoom, along with a special clip produced by The Simpsons team, in which Homer Simpson gave O’Brien — who once was a former Simpsons writer — an exit interview.

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