Conan O’Brien Talks Comedy Highs and Late-Night Lows in Stern Show Return

Comedian, late-night legend, podcast host, and Howard’s best interview of all-time Conan O’Brien returned to the Stern Show Tuesday for another epic sit-down covering everything from his early days at Harvard, “Saturday Night Live,” and “The Simpsons” to his musings on which qualities entertainment icons like Bruce Springsteen and Tom Hanks possess that make them so successful. The 59-year-old TV star turned podcast mogul spoke about the highs and lows of his late-night career, which included crawling underneath the desk in his “Late Night” office and watching the Rock repeat one of his zingers in the wrestling ring. He also broke big news regarding his new Team Coco Radio network, debuting Tuesday, Nov. 15 on SiriusXM channel 106.

The comedy channel launch is a big deal both for Conan’s fans — who will now get a chance to listen to Team Coco podcasts, segments from his recent TBS show, and all-new original content all day long — and Conan himself, who told Howard he’s spent the last 13 years trying to rewrite his future obituary.

In 2009, Jay Leno seemingly retired as host of “The Tonight Show” and handed the reins over to “Late Night” host and longtime network colleague Conan O’Brien. Less than eight months later, and for a variety of reasons that can and have filled a book, the network gave Leno back his old time slot and essentially forced Conan out. For years, the shake-up and apparent subterfuge was all Hollywood wanted to talk about.

“I remember at the time thinking, ‘Oh shit, now this is the first paragraph of my obit,’” Conan told Howard, explaining he then made it his mission to change the narrative by working hard and letting go of his anger. “I was furious for two years … but I kept my head down and now there are so many people around the world that know me from [other work].”

Over a decade later, Conan believes the late-night fiasco may finally be in his rearview. “It is generational. Younger people … know me from YouTube, and they like that stuff,” he said, adding, “Which I’m happy about.”

Howard wondered if Conan had seen Jay since the drama went down.

“Oh god, no,” Conan laughed. “He would pretend nothing happened, I’m pretty sure.”

Neil Young’s Performance on Conan’s Final ‘Tonight Show’

When news broke that Leno would take back “The Tonight Show,” rock legend and repeat Stern Show guest Neil Young was one of the first people to call Conan up and not only offer his support but also volunteer to appear on his final show. “It was such a beautiful thing. He was amazing,” O’Brien recalled, explaining Neil performed the bittersweet Stills-Young Band ballad “Long May You Run.” “He was, to use my people’s term, a mensch [about] the whole thing.”

In addition to praising the quality of Young’s character, Conan had kind words about his musical legacy. “He’s managed to stay completely authentic and raw in a way that almost seems impossible to me,” O’Brien marveled. “What he was doing with Buffalo Springfield in 1965 – he’s still going for that. He hasn’t calcified. He hasn’t crusted over … So, that guy blows me away.”

Conan also admired Stern Show veterans Bruce Springsteen and Sir Paul McCartney, which led to him and Howard discussing how mind-blowing it was to watch the two musicians craft iconic music with their otherwise ordinary seeming hands. “Those are the same hands [Bruce] uses to open up a bag of Doritos, and they’re no different than our hands,” Conan marveled.

Good Schools, Bad Crowds, and a Tall Glass of Shut-Up Juice

Conan dreamt of a career in show business from an early age but didn’t think he could get his foot in the door without first getting into a great school. “I worked my ass off,” he told Howard, explaining that despite getting into Harvard some subjects remained difficult. “I was not a gifted math student. I remember that being a huge impediment. I’m still phobic about math,” he said, explaining his children mock him whenever he struggles to calculate a tip.

Though he was grateful to graduate from Harvard, Conan doesn’t believe Ivy League educations are a magical solution to life’s problems. “I was very proud that I was accepted, I had a wonderful time there, [and] it got me into comedy … but it’s not Hogwarts,” he said, adding, “The most brilliant people I worked with, I don’t know where they went to college. Some didn’t even go to college.”

In the latter category was Tommy Blacha, a writer Conan met through his longtime collaborator Andy Richter. “[He was] one of the most original comedy minds I’ve ever met,” Conan said, adding that when Blacha left his show to work in pro wrestling, it unexpectedly led to one of O’Brien’s proudest comedy moments.

“I used to screw around with the writers a lot … I’d say, ‘Why don’t you go have a nice, tall glass of shut-up juice, alright?’” he recalled. “It was such a stupid put-down, but Tommy liked it, and then Tommy said, ‘Watch the match this weekend.’” Sure enough, Conan tuned in that night and saw the Rock telling his opponent to drink a “nice tall glass of shut-up juice.” “The crowd went crazy,” Conan said, explaining some fans even started making “drink some shut-up juice” signs for matches. “I was in heaven.”

Conan’s Harvard education proved to be a double-edged sword after he got his first late-night hosting gig. He was employing a skeleton staff at the time, so he let his trusted announcer Joel Godard warm up the live audience before the show. “We were so busy putting the show together that we weren’t paying attention to how he was warming up the crowd, and I would get up there and the crowds were rough,” Conan recalled.

At first, he chalked the ire up to having just replaced fan favorite David Letterman. But then he finally caught Godard’s warm-up act. “He’s saying … ‘Conan went to Harvard, where he majored in history and literature of America. He wrote a thesis on Flannery O’Connor and William Faulkner,’” Conan recalled with a laugh. “He was like, ‘And here he is, a man who is better than all of you. Here he is, a man who has never done an honest day’s work in his life.’”

O’Brien was stunned, but Godard thought he was doing his job. “He was like, ‘I just thought I was supposed to tell them about some of your accomplishments,’” he continued. “I was like, ‘No, Joel. We don’t mention that.’”

Parting Was Sweet Sorrow

Blacha isn’t the only one of Conan’s talented writers, staffer, and friends who has gone on to pursue other interests over the years. “My dream has always been – and it’s kind of come true – that a bunch of people who worked with me go on [and] do really cool things … [and] 10 years from now when I’m happy to get anything, they call me up and say, ‘Hey, do you want to do a walk-on on my really cool project?’” he told Howard. “I want my friends to thrive, almost in self-interest.”

An exception to the rule was his longtime sidekick Andy Richter, who left “Late Night” in 2000 and didn’t rejoin Conan’s show until 2009. “I was devastated,” O’Brien said of Richter’s departure. “I loved the guy, and he was so funny, and he was such an integral part of the show.”

Howard wondered if Conan had begged him to stay, but Conan said there was nothing he could say that Andy didn’t already know. “He knew I needed him,” Conan laughed, adding, “I’ve told Andy ‘I love you’ more times than I told my wife I loved her.”

His Darkest Moment

“Late Night With Conan O’Brien” will surely be remembered as one of the late-night landscape’s most innovate offerings, but as Conan reminded Howard on Tuesday, critics weren’t kind when the show premiered in 1993. “There were some really, really dark moments … We were just on the air for two or three months, and things weren’t going well, and then I did Charlie Rose’s show,” he told Howard, recalling how Rose ambushed him on air with a scathing review from TV critic Tom Shales. “It was an absolutely brutal takedown of me, Andy, the comedy, everything,” he continued. “Today, I don’t know if TV critics move the needle, but back then it was like this could ruin everything.”

Even so, Conan didn’t entirely disagree with the review. “I was very raw,” he recalled. “I always say that if I hadn’t been me, I would’ve hated me.”

After visiting Charlie Rose, Conan returned to his Midtown office, shut the door, and crawled under his desk. “[I] just laid there. At one point … someone from the show leaned in and just saw my legs coming out from under the desk,” he recalled. “From underneath the desk, I just said, ‘I’m fine. I just need to lie here under the desk for a while. I’ll start having meetings in like 10 minutes.’”

“That for me is when the needle got to the lowest,” he added.

Howard was stunned that Rose read the bad review on air. “It’s almost like he took you out in the middle of the town square and flogged you,” he laughed.

“I don’t hold it against him. He was nice to me … Do I wish he hadn’t read that on the air? Sure, but that was another day at work for him,” Conan laughed, adding, “Now, it’s so funny … I’ve had these famous highs and lows … but I wouldn’t change anything. I remember my dad said … a really smart thing: ‘If you can survive this, it’s gonna make the whole story better.’”

Conan Reveals His Best Guests

Howard famously noted Conan was his best interview of all time and on Tuesday, Conan revealed some of his own best guests — one being recent Stern Show visitor Bruce Springsteen. “He would show up early, he would rehearse, he knew all the cameramen’s names … he was a gentleman, he crafted it, he figured it out,” he said of Bruce, who appeared on his show several times over the years. “He doesn’t need to prove anything on ‘Late Night with Conan O’Brien,’ … he’s got nothing to prove to anybody, and then he’s hanging out afterwards and thanking people? … There’s a reason he’s Bruce Springsteen.”

Conan had similar feelings about another guest — actor Tom Hanks, recalling his appearances both on his talk shows as well as on “Saturday Night Live.” “He would show up early, he would have ideas, he brought stuff to the table,” he said before recalling a particular encounter with the 10-time “SNL” host. “I remember walking through the writer’s conference room once and he was lying on the conference table at like four in the morning, and he was like, ‘Conan, what do you got? What are you boys cooking up?’ Like, ‘I got an idea.’”

Moments like that with the actor left an impression on O’Brien. “You can see that this is why he’s Tom Hanks. It’s not that [they’re] Tom Hanks or Bruce Springsteen and then they’re trying to be a good guy,” he said of the two icons. “No, this work ethic, this ‘It has to be good, and I need to show people my appreciation’ … it’s emotional intelligence.”

How Bringing Springfield a Monorail Led to Singing With a Gay Men’s Chorus

Conan wrote and produced on “The Simpsons” for only a couple seasons before leaving to host “Late Night” in 1993, yet to this day fans still approach him about his short stint on the long-running animated comedy. “The thing [people] ask me about the most is … the monorail episode,” he told Howard. “’Simpsons’ fans really like that episode.”

As the credited writer on “Marge vs. the Monorail,” Conan drafted the outline for the story and came up with the idea to satirize “The Music Man” and film producer Irwin Allen. But he was still reluctant to accept too much praise for the script. “You go in the room with the most incredible writers … and they all start throwing in great jokes,” he said. “No one can claim sole credit for just about anything on ‘The Simpsons.’”

Decades later, that writing credit lead to an epic career moment when O’Brien performed “The Monorail Song” live at a 2014 “Simpsons” spectacular. “When ‘The Simpsons’ had a big anniversary show at the Hollywood Bowl, [producer] James L. Brooks asked me to come back and sing that song with the [Gay Men’s Chorus of Los Angeles], and it was one of the highlights of my life,” he told Howard. “I mean … me coming out dressed as the Music Man, singing this song that I wrote when I had a Ford Taurus and bad skin … and now here I am singing this in front of people at the Hollywood Bowl.”

“It was magical, and I do try to take those moments in,” O’Brien added.

Playing Andy Warhol at Weird Al’s Behest

O’Brien recently put his acting skills on display with a small part as pop artist Andy Warhol in “Weird: The Al Yankovic Story,” a Weird Al biopic starring Daniel Radcliffe as the legendary song parody maestro. Weird Al, who co-wrote the script, personally asked Conan to be in his movie. “The wig did most of the work,” he told Howard with a laugh, adding, “[Weird Al] just wanted to have some wacky cameos. I do not think I was chosen for my acting ability.”

To Conan’s mind, the strangest part about making a movie was waiting years for it to hit theaters. “I make a show, it goes out an hour later — that’s my whole life in show business — [but] I shoot this thing and I forgot I did it,” he said. “I started getting texts from [friends] saying, ‘Hey, liked you in the Weird Al movie,’ … I’m thinking, ‘Wait a minute, I’m in the Weird Al movie?’”

It can be hard for actors to know if a movie will be any good before they shoot it, but Conan wasn’t nervous about the quality of the final product. In addition to trusting Weird Al’s taste, he told Howard he was at a stage in life and career where he felt comfortable trying new things. “If it’s not good, I’ll apologize,” Conan laughed, explaining “I’m freer now than I used to be.”

John Candy Once Took Conan Éclair Shopping and Gave Him Career Advice

While Conan loved his future employer “Saturday Night Live” as a kid, it was the Canadian sketch comedy show “Second City Television” that really impacted him. “It was like finding a rare jewel … It was so funny, and it was the first time I thought … ‘They’re making this for me,’” he said of the discovery before noting a sketch called “Yellow Belly,” featuring one of his favorite “SCTV” performers, John Candy. “He plays this cavalry officer and was a coward … It’s John Candy shaking and a woman and a little daughter pass by … Yellow Belly turns around and shoots them in the back – I didn’t think you could do that. It is so wrong, and I laughed so hard.”

Eventually, Conan got to meet Candy when he presented him with an award while at the Harvard Lampoon. “We ended up hanging out and what I remember clearly is he was everything I wanted him to be. He was John Candy – he was over the top, funny all the time, called me kid,” the podcast host said before recalling visiting a pastry shop with the late actor despite being given explicit instructions that he was on the Pritikin diet. “They start stacking … all these different eclairs into a box … and he sees me looking at him … he nudges me, and he goes, ‘Don’t worry kid, they’re Pritikin éclairs.”

The memory of walking around Cambridge, Mass., with the comedy legend stuck with Conan – and Candy too. At some point, the comedian’s daughter reached out to Conan with photographs she discovered that he took from their excursion. “There are these pictures of me looking like an 11-year-old girl there at Harvard Yard from 1984,” he remarked. “It was just miraculous to think, ‘Wow, John Candy took these photos and had them in his closet somewhere.’”

Perhaps an even bigger gift was the advice Candy gave young Conan while at a Lampoon party. “I said to him, ‘Mr. Candy, I’m thinking I might try comedy,’ and his head just whipped around, he looked me right in the eye, and he said, ‘You don’t try comedy. You do it or you don’t do it,’” he remembered being told. “That hit me very powerfully … and I think that was my attitude going into it in ’85 … ‘I’m not going to take the LSAT, I’m not going to have a backup, this just has to work.’”

An Uncut Adam Sandler Gem

Conan, who lives in L.A. near his former “Saturday Night Live” colleague Adam Sandler, told Howard the actor and comedian was far from your typical neighbor. “In Los Angeles, no one just goes to someone else’s house and knocks on the door … People live next door to each other, and they never talk,” he said. “But I’ve been in my house when I’ve heard outside, ‘Coney! Coonnnneey!’ It’s Adam, outside my gate, yelling.”

Sandler’s exuberance was something Conan first noticed when they worked at “SNL” together in the early ‘90s. “That can be a grim place just because there’s so much pressure. It can be competitive,” he said. “[Adam] showed up and he was the most enthusiastic young kid, and just [like], ‘Isn’t it awesome? We’re here at “SNL,” and it’s the best.’”

“You could go to IHOP and get a very mediocre pancake, and he’d be like, ‘Oh buddy, this is just the best,” O’Brien continued. “I drafted off his enthusiasm and energy — and a lot of us did. He was just, ‘It’s all good! Can you believe we’re here? Isn’t this amazing?’ And I love that about him.”

Team Coco Radio debuts Tuesday, Nov. 15 on SiriusXM channel 106.