Watch the most awkward moments from the last time Jay Leno 'retired' from The Tonight Show

According to NBC, tonight will mark the end of Jay Leno's almost unbroken 22-year tenure as the host of The Tonight Show. Tonight's episode, like the rest of the those aired this week, will serve as a tribute to Leno, complete with a slew of celebrity guests and a highlight reel from his time with the show. Leno's successor Jimmy Fallon even appeared on Monday's episode, offering a warm tribute to the late-night host.

If all of that sounds eerily familiar, it might be because you remember the last time Jay Leno retired, in the halcyon days of 2009. The Tonight Show's official YouTube channel has scrubbed all clips from Leno's 2009 "farewell episode," but a little YouTube sleuthing turned up a Today Show highlight reel of the short-lived transition between Jay Leno and Conan O'Brien. "Now, to the end of an era. After 17 years, tonight is Jay Leno's last as the host of The Tonight Show," says The Today Show's Natalie Morales in the tribute.

She was wrong. Leno did move, as promised, to the 10 PM slot on The Jay Leno Show — for about seven months, until NBC essentially squeezed Conan out and handed the Tonight Show mantle back to Leno. (For a thorough summary of what happened, read Bill Carter's The War for Late Night: When Leno Went Early and Television Went Crazy.)

Subscribe to The Week

Escape your echo chamber. Get the facts behind the news, plus analysis from multiple perspectives.

SUBSCRIBE & SAVE

Sign up for The Week's Free Newsletters

From our morning news briefing to a weekly Good News Newsletter, get the best of The Week delivered directly to your inbox.

From our morning news briefing to a weekly Good News Newsletter, get the best of The Week delivered directly to your inbox.

Sign up

Of course, you'd never have guessed any of that would happen at the time, which makes this short video — which purports to document "the changing of the guard at an American institution" — more than a little awkward.

"He's ending much like he began," said NBC's Lee Cowan in the clip. "His first guest, back in 1992, was comedian turned singer Billy Crystal." (Crystal will, once again, be Leno's alleged "final guest" on tonight's episode.) In the 2009 farewell, Crystal brought along a gospel choir to serenade Leno to the tune of "Movin' On Up."

"Movin' on down. Down to primetime. So I don't know why I'm singing goodbye," sang Crystal. "Movin' on down. Down to primetime. You'll be back in the blink of an eye." Right you were, Crystal!

Leno himself called it a "bloodless transition" to his then-successor, Conan O'Brien, though it would be just a year before NBC triggered the Red Wedding of the late-night TV landscape. Deadline managed to track down an even more damning quote from the era: "You were the only choice, you were the perfect choice," said Leno on live TV to Conan O'Brien, in an appearance shortly before O'Brien took over The Tonight Show.

As others have pointed out, it's basically the exact same thing Leno has said about Fallon over the past few weeks — so watch your back, Jimmy. If you need any more motivation, cheek out the end of this clip, in which Conan O'Brien said he's more than happy to let Leno enjoy the spotlight on his way out the door.

"It's Jay's night, so I wanted to do anything to make sure that it's just fun and that it's really about Jay," said O'Brien. "Because it's certainly not my night. God knows I'll be having my turn."