In a deal that had been worked out five years prior, Jay Leno left "The Tonight Show" to Conan O'Brien in 2009, but would take it back seven months later.
It was one of the messiest periods in late-night television history, and Jay Leno still has thoughts about it. He also has an apology for one late-night host, but not the one most people might expect.
Speaking with Bill Maher on his "Club Random" podcast, Leno insists he never intended to "deliberately sabotage" Conan O'Brien's "Tonight Show." "It doesn’t work that way," he insisted. "You’re trying to do the best you can."
The show that Jimmy Fallon has been hosting for more than eight years now used to be the biggest show in late-night television, and the brand every late-night host coveted. For years, David Letterman was considered the heir apparent to Johnny Carson's "Tonight Show" throne, airing behind him on "Late Night."
It was a huge and controversial situation when Letterman suddenly didn't get it in favor of Leno, leading Letterman to head to CBS where he set up the "Late Show" franchise Stephen Colbert is currently helming.
But that would only prove to be the first time the public accused Leno of screwing over another "Late Night" host. When Letterman jumped networks, Conan O'Brien settled in as the new host of "Late Night."
Just as Letterman had anticipated a big promotion to "The Tonight Show" when Carson retired, only to have NBC hire Leno instead, O'Brien expected that when Leno stepped away, the gig would be his.
He even secured that deal five years in advance, which Leno didn't seem super thrilled about at the time as it meant that rather than how Carson chose when to retire, Leno's end date was etched in stone. Or maybe we should say it was etched on an Etch-a-Sketch.
When five years had passed, Leno was still dominant in the ratings, so NBC came up with a completely bonkers idea. To save money on programming, they decided to create a new late-night show for Leno -- "The Jay Leno Show" -- and air it five nights a week in prime time!
Now, Leno would air every night at 10 p.m ET, followed by the local news and then O'Brien's "Tonight Show." Jimmy Fallon was brought in to take over O'Brien's slot as host of "Late Night." Many felt that by having Leno still on every night and before O'Brien, it was a slap in the face to the new host of the "Tonight Show."
The biggest problem for the network, though, was that both shows took a nosedive in the ratings. O'Brien didn't match Leno's numbers on "The Tonight Show," and Leno was a disaster in prime time. So do you give O'Brien time to find his audience and grow his ratings like Colbert has done with time on CBS, eventually overtaking Fallon -- or how Leno himself needed time to surpass Letterman's early ratings? Of course not!
NBC had yet another ill-fated idea, suggesting they were going to move Leno back to the 11:35 p.m. ET time slot for a half-hour version of "The Jay Leno Show," with O'Brien's "Tonight Show" now airing after midnight. This latest indignity, as many in the press and fans considered it, was the final straw.
O'Brien said if this happened, he would not stay on as "The Tonight Show" host, which was apparently just fine with NBC. The network bought out his contract and reinserted Leno as "The Tonight Show" host, leaving O'Brien to set sail for TBS and his long-running "Conan" talk show there. Leno would stick around and finally retire in 2014, with Fallon moving up from "Late Night" to take over.
The whole thing was very messy and ugly, playing out in the media, and many fans blamed Leno for just not being able to go away gracefully when the agreed-upon transition from him to O'Brien arrived. But as he told Maher, that's just not how it happened.
His decision to stick with NBC he said was in part because "this all happened fairly quickly." As such, he decided to stick with the network he knew than try something different. "I just figured let’s just play this out and see what happens."
At the time and with his scheduled retirement looming, Leno was being courted by several networks. One of those networks was ABC, with the proposal that Leno take over the 11:35 p.m. ET time slot and knock "JImmy Kimmel Live!" back a full hour to compete directly with "Late Night." Apparently, Kimmel even agreed to this deal, though Leno never actually took the network up on it.
"I suppose I should have called Jimmy and explained to him again, but I didn't," Leno admitted. "I don't know why I didn't. I just didn't. I thought he probably would figure it out. But I think maybe he was hurt by that, and I apologize to him for that."
He had no bitterness, either, about Kimmel's jokes about the messy late-night situation. "It’s just one of those awkward situations where he was a huge Letterman guy and when Letterman didn’t get 'The Tonight Show,' somehow it was my fault," Leno told Maher. "I think he resented that and I get that. But, Dave never had 'The Tonight Show.'"