Highlights
- David Letterman defended Conan O'Brien from Jay Leno's actions, calling out Leno's behavior in a joking monologue that received audience cheers.
- Howard Stern warned Conan in 2006 that Leno wouldn't let him host 'The Tonight Show,' a prediction that came true in the end.
- After NBC decided to replace Conan O'Brien with Jay Leno as host of 'The Tonight Show,' O'Brien walked away with a large settlement and landed a show with TBS.
David Letterman has been a fixture on late night television for decades. Over the years, he built a career on his trademark humor, wit, and interviewing style. Letterman has also received a lot of attention over the years for his rivalry with fellow late night host Jay Leno.
While Letterman has chosen not to hold a grudge against Leno in their own battle, he had no problem defending Conan O'Brien in his battle with the former Tonight Show host.
When O'Brien was brought in to replace Leno as host of the popular late night show, it was short-lived. Leno eventually took the gig back and O'Brien was out. During one of his monologs, Letterman defended O'Brien, resulting in cheers from his audience.
David Letterman Poked At Jay In His Monologue When Conan's 'Tonight Show' Gig Came To An End
On April 28, 2011, Letterman mentioned Leno's birthday during his opening monologue.
"Happy Birthday to Jay Leno, 61 years old today," he began. "Happy Birthday Jay."
Letterman continued, "Jay, of course, one of the few tyrants still alive," which resulted in cheers and applause from the audience.
Letterman then made a joke which seemed to defend Leno's rumored nemesis, Conan O'Brien.
"All of his friends got together and had a party," he said. "They had a cake and Jay cut the cake with the same knife he stuck on Conan's back."
Letterman also commented on Leno's plea to the public not to blame O'Brien for what was happening.
"No one is blaming Conan," Letterman said.
Letterman also told his audience that this incident sees Leno behaving exactly how he knew him to be. While speaking with Oprah Winfrey on Oprah's Next Chapter in 2013, Letterman addressed his own feud with Leno.
"Jay and I were friends — we were always friends, before all of this happened," Letterman said, referring to the moment Leno took over Johnny Carson's spot.
Letterman also revealed that those involved with The Tonight Show approached him to take over. Letterman asked them if Carson approved of the idea, but was told Carson didn't know about their asking him. Letterman told them that he wouldn't take the job unless Carson approved.
According to Letterman, Leno was announced as Carson's replacement shortly after that.
Letterman also told Winfrey about the time he spent with Leno in the early years. He said that whenever a fellow comic bombed, Leno would gather a group of comics to watch their performance and make fun of them. Letterman said that this would make him uncomfortable.
RelatedDavid Letterman Once Told Oprah That Jay Leno Is 'The Most Insecure Person I've Ever Known'
David Letterman and Jay Leno have a bumpy history filled with ups and downs.
"I’ve never met anyone quite like Jay. And I will say, and I’m happy to say, I think he’s the funniest guy I’ve ever known," Letterman said.
"Just flat out. If you go and see him do his nightclub act — just the funniest, the smartest, wonderful observationist and very appealing as a comic. Therefore, the fact that he is maybe the most insecure person I have ever known — I could never reconcile that."
Howard Stern Warned Conan In 2006 That Jay Leno Wouldn't Let Him Host 'The Tonight Show'
Talk of Conan O'Brien possibly hosting The Tonight Show had been buzzing long before the comedian took the job. This is something Howard Stern was aware of when he appeared on Late Night with Conan O'Brien in 2006.
During his interview, Stern brought up the possibility and warned O'Brien that it might not be such a good idea.
"I don't see this guy leaving and letting you walk in. I'm concerned about you," Stern told O'Brien about Leno.
Stern then joked that he saw Leno as someone who "stares at the wall ... and waits to go to work. He doesn't do anything but work."
Stern has never hid the fact that he dislikes Leno. When he appeared on the Late Show with David Letterman in 2009, he joked with Letterman about having to compete with O'Brien, referencing Letterman's rumored feud with Leno.
"This Conan O'Brien took over the Leno show. You heard about this?" Stern asked. "We got to beat this Conan. For God's sake, how are you feeling? Jay left late night television and now you've got this new guy to compete with?"
RelatedHoward Stern Warned Conan O'Brien About His Deal With Jay Leno Falling Through Even Before Leno Refused To Leave
Howard Stern has made his distaste for Jay Leno well known, but one comment on "Late Night with Conan O'Brien" appeared to be prophetic.
In 2010, Stern continued to speak about Leno during an interview on The Early Show. In the aftermath of Leno's return to The Tonight Show, Stern called Leno "a thief."
"He lifts bits directly from my show," Stern said. "‘Jay-Walking’ was lifted from my radio show!"
Stern also called Leno a "lapdog" for NBC and claimed he "sabotaged" O'Brien. Stern said Leno "makes me want to vomit."
Conan Said He Believed NBC No Longer Wanted Him On The Network
After O'Brien was hired as the new host for The Tonight Show, NBC decided they wanted to move his time slot. Instead, they would give the original time slot back to its previous host, Jay Leno. O'Brien decided to walk away and received a $32 million settlement and a new show on TBS.
In 2010, O'Brien reflected on the ordeal with CBS News. NBC's decision brought them a lot of bad publicity and a large amount of public support for O'Brien followed.
"That first day that I woke up and was no longer the host of The Tonight Show, I remember the first thought I had is 'I am not shaving.' And that was my small victory, you know. 'Ok, so I lost The Tonight Show but I'll show them, I'll stop shaving," O'Brien said when the reporter asked about his beard.
"This year has been, is still incomprehensible to me. The amount of stuff that's happened in my life in the last year is…it's gonna take me a long time to process it," he added.
"It just felt like the tone went very quickly from, 'Take your time, we understand this is a tough decision,' to you know, 'Let's go,'" O'Brien said. "And that probably helped me a little bit feel like, 'You know what? This environment doesn't feel right and I've been with these people a long time. And I don't like, I really don't like the way this is going.' And when it started to get toxic and I started to feel that I'm not sure these people even really want me here. Let's just…I can't do it."
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