Why Conan O'Brien & Jay Leno Hate Each Other: The Tonight Show Feud, Explained

You may not know that many of the current late-night hosts are good friends, but they definitely are. During the WGA and SAG-AFTRA strike, five hosts — Seth Meyers, Jimmy Kimmel, Jimmy Fallon, John Oliver, and Stephen Colbert — worked on a short-lived podcast called "Strike Force Five," and it's not uncommon for any of those people to appear as guests on each others' respective shows. These sort of friendships are relatively commonplace, but there are two famous former late-night hosts who really hate each other: Jay Leno and Conan O'Brien.

So what exactly happened here? Let's begin with a little backstory. After original host Johnny Carson left NBC's late-night institution "The Tonight Show" in 1992, Leno took over, despite Carson's apparently direct wishes that the job go to his chosen heir David Letterman. This marked the first of two disputes that Leno would engage in over "The Tonight Show," and it's also important to note that Letterman was an important mentor to O'Brien throughout the latter's career, which, it could be said, placed Leno and O'Brien at opposite ends of the proverbial boxing ring before contract negotiations even began.

Ultimately, in 2009, Leno ceded "The Tonight Show" to O'Brien, accepting NBC's offer for a primetime slot at 10 P.M. EST (with "The Tonight Show" in its same slot at 11:30 P.M. EST). From there, the situation seriously devolved, and the end result led to O'Brien leaving the network all together — as well as a bitter and lengthy feud between O'Brien and Leno.

When "The Tonight Show with Conan O'Brien" and "The Jay Leno Show" premiered in 2009, ratings for O'Brien's show were fairly solid at the outset, whereas "The Jay Leno Show" didn't fare quite as well. The troubles for both shows persisted, with O'Brien's mentor David Letterman frequently crushing "The Tonight Show" with his version, "The Late Show with David Letterman" (the show crafted by CBS that lured Letterman from NBC to the new network). NBC's entire framework looked like it was crumbling, with even its local news affiliates seemingly affected by the new host of "The Tonight Show" and Leno's 10 P.M. outing; in an article in New York Magazine, industry expert Mark Harris tried to explain what was going on. "Handing 10 p.m. to Leno has also hurt ratings—severely in some cities—for the late-night newscasts of NBC's affiliates," Harris wrote. "That, in turn, has dinged the 'Tonight Show,' which, in the shaky hands of Conan O'Brien, now loses to David Letterman (who, even mid-scandal, seems to be having the time of his life)."

What this all led to is that Zucker and other NBC executives decided they wanted to simply bump "The Tonight Show" back to a midnight slot — somewhat invalidating the word "tonight," as it would really air in the wee hours of the morning — and have Leno follow the evening news instead at 11:30, just like he did as the host of "The Tonight Show." Infuriatingly, O'Brien's contract apparently didn't prevent the network from doing this.

When the plan to move "The Jay Leno Show" to 11:30 P.M. EST officially in motion, "The Tonight Show with Conan O'Brien" was officially pushed back to 12:05 AM EST, with the change set to take place in early 2010. After O'Brien was informed of these changes — in a meeting that, based on descriptions in Bill Carter's book "The War for Late Night," didn't go particularly well — the comedian released a statement addressed to "People of Earth" on January 12, 2020. 

O'Brien began by asking his fans not to "feel sorry" for him, aware that hosting late-night shows is a privilege and not a right, but he was also fully unequivocal about his feelings. "Last Thursday, NBC executives told me they intended to move the 'Tonight Show' to 12:05 to accommodate the 'Jay Leno Show' at 11:35," one part of the statement read (per The New York Times). "For 60 years, the 'Tonight Show' has aired immediately following the late local news. I sincerely believe that delaying the 'Tonight Show' into the next day to accommodate another comedy program will seriously damage what I consider to be the greatest franchise in the history of broadcasting. The 'Tonight Show' at 12:05 simply isn't the 'Tonight Show.'" O'Brien concluded by saying he would no longer host "The Tonight Show."

After a lengthy legal battle, O'Brien left NBC with $45 million — including hefty severance pay for his staff, which O'Brien reportedly demanded — and he wasn't allowed appear on television until September of that year.

So what did Jay Leno — who returned to host "The Tonight Show" after Conan O'Brien left NBC — have to say about the whole thing? In 2022, Leno appeared on "Club Random," the podcast run by HBO late night shock jock Bill Maher, and pushed back against Maher's assertion that Leno "deliberately sabotaged" O'Brien's run on the late night institution.

"That doesn't work," Leno said regarding the idea that he agreed to his primetime show in order to ruin O'Brien's chances of success. "It doesn't work that way. You try and do the best you can and it didn't work."

Despite also saying in the interview that he toyed with moving networks when "The Jay Leno Show" underperformed, Leno admitted that he stayed at NBC — and took his old job back — because it felt safe. "Sometimes the czar you have is better than the one you're going to," he said to Maher. "Then you have your old team shooting at you as well. I just figured let's just play this out and see what happens. This all happened fairly quickly."

Leno left "The Tonight Show" in 2014, actually ceding the show this time to Jimmy Fallon. After that, he continued working as a stand-up comedian, hosted game shows like "You Bet Your Life" and served as a guest judge on shows like "Hot Wheels: Ultimate Challenge" and "America's Got Talent.

It's safe to say that, despite the truly awful situation Conan O'Brien faced over "The Tonight Show," his career has been doing just fine since then. After leaving "The Tonight Show," Conan accepted a deal with TBS and hosted the eponymous late-night show "Conan," which ran from 2010 to 2021 — and some of the segments from that, called "Conan Without Borders," became breakout sensations (that one even earned O'Brien and his staff an Emmy). Since 2021, the comedian has hosted a popular interview podcast, "Conan O'Brien Needs a Friend," and in 2024, his Max original series "Conan Must Go" — a new travel series — premiered to great acclaim. (There's also his "Hot Ones" episode that aired ahead of the show's premiere, which immediately went viral and had social media buzzing about O'Brien's funniest moments.)

O'Brien has been clear, though, that there's no love lost between him and Jay Leno. In November of 2010, he told Playboy (via The Hollywood Reporter) that he'd never host Leno on "Conan," saying, "No, there are certain things I will not do, regardless of the price." That same year, he told "60 Minutes" (via IndieWire) he would never have done what Leno did. "He went and took that show back and I think in a similar situation, if roles had been reversed, I know — I know me, I wouldn't have done that," O'Brien said, saying he would never have "surrendered 'The Tonight Show' and handed it over to somebody publicly and wished them well — and then ...six months later [reclaimed it]."

"Conan Must Go" is streaming on Max now.