Every celebrity has had their fair share of awkward interviews. Whether because they like to purposely act awkward during talk shows like some fans believe Aubrey Plaza sometimes does or because the interviewers ask the most inappropriate questions.While some stars know exactly how to act during awkward interviews, like the way Anne Hathaway handled her interview with Matt Lauer, others would rather avoid these kinds of interviews altogether.Conan O'BrienBelieve it or not, late-night hosts can also have the most awkward interviews. That’s why some of them try to avoid certain topics or simply avoid inviting certain celebrities to their shows. In fact, television host and comedian Conan O’Brien has admitted he’d rather not have Jay Leno on his show, no matter the price.Related: 10 Times Things Got Weird In A Conan O'Brien Interview

Conan O’Brien’s Career Changed For The Best Thanks To Some Advice From This Friends Star

Conan O’Brien is one of many other celebrities that went to college before making it big in Hollywood. Believe it or not, this popular comedian attended Harvard University. He majored in history and literature and graduated on top of his class.

Shortly after graduating, he moved to Los Angeles and joined the writing staff of HBO’s sketch comedy series Not Necessarily the News.

Conan O'Brien at The 2014 MTV Movie Awards
Instar

O’Brien wouldn’t get his big break as a writer and comedian until 1988 when he was hired as a writer for the popular sketch comedy show Saturday Natural Night. Like many other SNL writers, O'Brien occasionally appeared as an extra in some sketches.

His most notable appearance was as a doorman in a sketch with Tom Hanks back in 1990. A year later, O'Brien quit SNL because he was feeling burnout.

After his departure from SNL, O’Brien was invited to work as a writer and producer for The Simpsons. He worked on this animated sitcom from 1991 to 1993. After this, his career would take a turn for the best after Friends alumn Lisa Kudrow pushed him to become a performer rather than just focus on writing.

Related: Conan O'Brien Is Set To Double His Net Worth, Here's How

Since then, O’Brien has been working as a host for late-night talk shows for almost 28 years. His career as a host began with Late Night with Conan O'Brien (1993–2009) and The Tonight Show with Conan O'Brien (2009–2010), both for the NBC television network.

Then he went on to host Conan (2010-2021) on TBS. Most recently, he started hosting the podcast series Conan O'Brien Needs a Friend and it’s been announced that he’ll launch a new show on HBO Max.

Are Conan O’Brien And Jay Leno Feuding?

Jay Leno is better known for his job as a television host, comedian, writer, and actor. His career started with minor roles in television series and movies such as Good Times, Fun With Dick and Jane, and American Hot Wax. And his first appearance on The Tonight Show was back in 1997, performing a small comedy routine. He also had numerous appearances on Late Night with David Letterman over the 70s and 80s.

After working as an actor and stand-up comedian for several years, Leno became the host of NBC’s The Tonight Show in the early 90s. He’d host this show until 2009 when Conan O’Brien was hired to take over as host of the show. This sparked a feud between the two hosts and the TV network.

Although NBC had told Leno in anticipation that O’Brien would be taking over hosting The Tonight Show in 2009, the comedian and actor wasn’t happy when his time to leave the show came around.

As a compromise, NBC offered Leno a nightly primetime show before O'Brien's show.

Upon Leno’s complaints, the broadcasting company tried to return Leno to his original time at 11:35 pm ET and move O'Brien’s show a half-hour later, to 12:05 am ET. But Conan O’Brien refused to compromise. At the end of the day, O’Brien left the network and moved to TBS to host Conan instead.

Meanwhile, Leno returned to hosting The Tonight Show until 2014, when he retired. After these events, it’s safe to say that these two television hosts don’t have the best relationship.

Related: Conan O'Brien May Be In A Celebrity Feud With This Beloved Comedian, Here's Why

Here’s Why Conan O’Brien Refused To Interview Jay Leno On His Show

Even today, more than a decade after the 2010 Tonight Show conflict between Jay Leno and Conan O’Brien took place, the two television hosts don’t have the best of relationships. In 2010, O’Brien admitted that he wouldn’t have Leno over at his new talk show. And, true to his word, Leno never made an appearance in Conan.

“He can come as the musical guest because that I want to see; no one knows he has an operatic range,” O’Brien joked after admitting he wouldn’t like to interview Jay Leno on any of his shows.

And when he was asked if money could make him change his mind, the late-night host replied, “No, there are certain things I will not do, regardless of the price.”

Clearly, O'Brien had enough.