Jimmy Kimmel makes a dig at Jay Leno while bidding adieu to Conan
Jimmy Kimmel has always been Team Conan, so during his monologue on Thursday's Jimmy Kimmel Live, the late-night host congratulated his friend on wrapping up Conan — while also taking a jab at Jay Leno.
"I also want to congratulate Conan O'Brien on 28 years of very funny late-night television. Conan wrapped up his show on TBS tonight," Kimmel told his audience.
"Anyway, here's to Conan and Andy Richter and everybody involved with that show," he continued. "We look forward to whatever you have planned next at HBO Max. And I also want to say, congratulations to Jay Leno on his new time slot at TBS."
Kimmel's joke was a more-than-decade-old reference to the much-documented late-night dust-up between O'Brien, Leno, and NBC. Essentially, the quip was an opportunity to once again chide Leno for handing the reins of The Tonight Show over to O'Brien in 2009, and then signing on to do a prime-time show (the ill-fated Jay Leno Show) that aired before O'Brien's Tonight Show. But that's not all: Leno then came back to The Tonight Show, when O'Brien's brief hosting stint came to an end after O'Brien turned down NBC's request to bump his Tonight Show to the 12:05 a.m. slot (following Leno's show moving to 11:35 p.m.), and the two parties reached an exit deal.
At the time, Kimmel was one of O'Brien's most vocal supporters, and he used the headline-garnering situation at NBC to his comedic advantage.
In 2010, Kimmel appeared on Leno's 10 p.m. show and blasted him during this 10@10 question segment. For example, one of Leno's questions was about the best prank he ever pulled. Kimmel responded, "I told a guy that five years from now I'm going to give you my show, and then when the five years came, I gave it to him, and then I took it back almost instantly."
The late-night host also helmed an entire episode of Jimmy Kimmel Live while dressed as and parodying Jay Leno.
"Hello, hello, I'm Jay Leno. Let it hereby be known I'm taking over all the shows on late night," Kimmel joked in his monologue back in 2010. "You know what ABC stands for? Always bump Conan."
Leno later went on to tell Oprah Winfrey he felt "sucker-punched" when the 10@10 segment happened.
While Leno took the blame for the Tonight Show debacle, 60 Minutes reported in 2014 that it was NBC who offered O'Brien the Tonight Show gig in 2009 (during 2004 contract negotiations), and Leno didn't find out about the deal until later.