Conan O’Brien Told Howard Stern He Battled "Depressive" Self-Esteem Issues At The Highest Point Of His Career

Summary

• Conan O'Brien struggled with depression during his time hosting Late Night, especially after receiving bad reviews and a brutal takedown of his performance. It was a difficult period for him.
• Losing The Tonight Show after just a year caused O'Brien to feel depressed and like he was going through a sudden and violent breakup. However, doing his comedy tour helped him feel better and heal from the experience.
• O'Brien made the decision to end his show Conan on TBS and move to HBO Max, where he will be hosting a new variety show. He joked about Johnny Carson's advice to get to a streaming platform as soon as possible, and he is excited about the new opportunity.

Conan O'Brien has been open about struggling with depression despite being secretive about his personal life, especially his marriage. One of his low points was his short-lived stint on the The Tonight Show, which pitted him against his predecessor, Jay Leno. But as it turned out, O'Brien also had his "dark moments" as a success in Late Night.

In an interview with Howard Stern, O'Brien said he felt depressed after the bad reviews on his early Late Night episodes. But what really hit him was a "brutal takedown" of his performance, which Charlie Rose brought up during their interview. Here's how the comedian ended up hosting the show for 18 seasons before his failed The Tonight Show and recent transition to the streaming business.

Conan O'Brien Was Depressed When He Took Over 'Late Night'

In their 2022 interview, Stern told O'Brien, "for a guy like you, who eventually needed something to get some help with an antidepressant, I can't imagine the s--t you went through when you first took over Late Night." The guest added that he "wasn't on anything then" and that he "didn't have the knowledge that I had today... And there were some really really dark moments." He then talked about the time when they "were just on the air for two or three months, and things weren't going well."

Back then, he went on Charlie Rose where the host was "aware" of Washington Post's negative review of O'Brien's Late Night. "The top TV critic in the world just wrote this piece, and here's what it says," the latter recalled. "And it goes. And it was a brutal takedown - just absolutely brutal takedown of me, Andy, the comedy, everything... Back then, this could end everything." O'Brien said "he didn't think [the review] was wrong" and that if he "hadn't been me, I would have hated me."

On how Rose's interview crushed him, he said: "He was being a journalist, I guess. He read this thing to me. And so I'll never forget... We get in this town car, me and my people. Everyone is silent. We get to work, and I quietly get to my office and no one in the office is saying anything."

"And I go into my office... I got on the floor and I climbed under the desk and just lay there," O'Brien continued. "Someone on the show leaned in and saw just my legs coming out from underneath the desk. And then the next thing I know, Jeff Ross, my executive producer, is just leaning in, going like, 'You okay? Everything alright?'"

The talk show host told Ross he was "fine" and that he just needed to "lie here under the desk for a while." He said that was when "the needle got to the lowest." Stern added that it having no therapist or antidepressants must have made it so hard on O'Brien. He even thought Rose "took [O'Brien] out in the middle of the town square and flogged" him.

Howard Stern has been a vocal critic of Jay Leno whom he accused of sabotaging Conan O'Brien.

Conan O'Brien Got Depressed About His 'Tonight Show' Exit Caused By Poor Ratings

In 2001, O'Brien received a contract to replace Leno on The Tonight Show in 2009. But NBC only informed the latter in 2004. The former only had the gig for a year, which caused the network to reinstate Leno as host in 2010 until his retirement in 2014. O'Brien and his team were given $45 million ($60 million in 2022) to give up the gig. Months later, he moved his show Conan to TBS.

In May that year, O'Brien told CBS' Steve Kroft that he stopped shaving after learning he was removed from the Tonight Show. "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,'" he shared. "And that was my small victory, you know. 'Ok, so I lost the Tonight Show but I'll show them, I'll stop shaving,'"

Despite saying his one-year stint was "a lot of fun," O'Brien said he "got very depressed at times. It was like a marriage breaking up suddenly, violently, quickly."

"And I was just trying to figure out what happened," continued the former SNL writer. "When we started putting this tour together, I started to feel better almost immediately. And then there is almost no better antidote to what I've just been through than to do this every night."

Talking about whether the saw Leno getting his job back, he said: "I'm a paranoid person. And I think I'm the kind of person that can come up with lots of negative scenarios. But I remembered thinking that seemed like that was a stretch even for me." Here's a full timeline of Leno and O'Brien's feud:

Conan O'Brien Ended TBS' 'Conan' To Start An HBO Max Variety Show

In June 2021, O'Brien decided to end his TBS show, Conan, 28 years since he started as a late night talk show host. The decision came three years after a hiatus that brought back the show, reduced to a simpler, half-hour program. The franchise had a total of 11 seasons.

Talking about his late-night TV exit, the host joked: "In 1993, Johnny Carson gave me the best advice of my career: 'As soon as possible, get to a streaming platform.'"

O'Brien has decided to foray into HBO Max with the four-part international travel series, Conan O'Brien Must Go. "I'm thrilled that I get to continue doing whatever the h--l it is I do on HBO Max, and I look forward to a free subscription," he quipped. The trailer is out, but the release was postponed due to SAG-AFTRA's strikes. It's said to air in 2024.

Conan O'Brien is worth $200 million, while the frugal Jay Leno is worth $450 million.