NBC’s Massive Goof-up with Conan O’Brien and Jay Leno That Cost Them a $45 Million Settlement

Conan O’Brien is going to host the Oscars this year and recently he talked about how the LA fire has impacted the Academy Awards planning. Some even questioned whether the Oscars would get canceled or not. However, the organizers have announced that they will arrange an award ceremony that unites the industry and respects whoever fought in the fire. Talking about the Oscars, in an interview, O’Brien said that everyone wants to be sensitive to the moment and to what has happened.

O’Brien is one of the well-known talk show hosts who formerly led Late Night from 1993 to 2009, and earned a lot of acknowledgment. Last year, the talk show host also appeared on The Tonight Show as a guest of its now host Jimmy Fallon. For those who don’t know, there was a huge conflict between O’Brien and Jay Leno which led him to exit the show. His reunion with the show resurfaced the old memories. Read ahead to find out what happened.

What happened between Conan O’Brien and Jay Leno?

Before Seth Meyers could take over Late Night, Conan O’Brien used to host the show. It was one of the most popular talk shows back in the day. However, the conflict between O’Brien and Jay Leno was years in the making. Leno used to host The Tonight Show after Johnny Carson’s retirement and before Jimmy Fallon‘s tenure.

It all started in 2001 when NBC extended O’Brien’s contract promising him to make the next The Tonight Show host. Unaware of the whole agreement, Leno continued his job till 2004. However, in 2009, when things started to take a different turn, to keep both of the stars, NBC offered Leno a primetime slot before O’Brien – The Jay Leno Show. Neither of the shows worked and after getting poor ratings, they shifted Leno to Late Night and pushed O’Brien’s show half an hour late.

With all these disasters, in 2010, O’Brien exited NBC and released a statement, “I’ve been suddenly put in a very public predicament and my bosses are demanding an immediate decision.” He further noted,

Six years ago, I signed a contract with NBC to take over The Tonight Show in June of 2009… I worked long and hard to get that opportunity, passed up far more lucrative offers, and since 2004 I have spent literally hundreds of hours thinking of ways to extend the franchise long into the future. I cannot express in words how much I enjoy hosting this program and what an enormous personal disappointment it is for me to consider losing it.

In his statement, responding to the change in time slots, the host shared that he couldn’t be a part of something that he believed was a destruction.

How did NBC settle the situation with Conan O’Brien?

After two weeks of rigorous negotiations, on January 21, 2010, it was declared that Conan O’Brien and his staff received $45 million from NBC as a settlement, leaving the network and O’Brien agreeing to a contractual seven-month ban from appearing on television. Cut to November 10, 2010, O’Brien started to host Conan on TBS till 2021. On the other hand, Jay Leno continued to host The Tonight Show till he retired in 2014.

In 2024, O’Brien returned to The Tonight Show as a guest to Jimmy Fallon. Being on the set of a show where he could never have a peaceful episode, the former host admitted, “It’s weird to come back… I haven’t been in this building for such a long time, and I haven’t been on this floor in forever.”

He further added, “I was here for 16 years doing the Late Night show before we went out to LA, and right across the hall, all these memories came flooding back to me.” Well, now in 2025, O’Brien will be seen as the Oscars host.