And Now, Here He Is… Conan O’Brien, Finally Comfy in Success

UPDATED: May 22, 2023
PUBLISHED: October 30, 2014

Conan O’Brien laughs as he mentions how articles about him, especially in the early days, would talk about how easily things had come to him. It’s ironic now, in hindsight. So he can’t help making a joke about being interviewed by SUCCESS magazine.

“Is there another magazine called Failure?” O’Brien asks. “Because I’ve done that cover about four times.”

The lanky redhead with the sharp blue eyes has seen some boulders on the road to his success as a late-night talk show host and has negotiated a route that has taken him to a good place. Married with two kids, he’s got a happy home life, a production company—Conaco—and a popular cable talk show. Conan has been renewed through 2018 by TBS, adding three years to his previous contract.

“Conan not only brought an incredibly young audience to TBS, but has also created a digital presence that draws millions of fans to his unique brand of humor,” says Michael Wright, TBS president and head of programming.

O’Brien, who looks and acts like a gangly teenager in search of mischief, has always appealed to a young audience. “When I am being silly and something is making me laugh, I act like I’m 15 years old, and people think I’m 15 years old,” O’Brien says. “It’s kept me young.”

Social media was not second nature to him, but “I decided a few years ago that I had to embrace this new technology or die. People will say, ‘I love that Taylor Swift thing,’ and I can’t remember if it was on the show, on the Internet, or maybe I’m dating Taylor Swift,” O’Brien says. “Younger people don’t see the distinction. They don’t care when I’m on or where I’m on.”

That’s dramatically different from the world in which O’Brien, 51, was raised. “I thought the mission of being a talk show host was being like [Johnny Carson] and having people watch you on TV,” O’Brien says. “But the mission is to be funny and honest with your instincts, and trust it will get out on TBS, the Internet, on Google Glass, or get you a drink in Taiwan. It doesn’t matter how people get it, just that they get it.”

Big Breaks

Things have come full circle for O’Brien, who seemed incapable of missteps early on. The Massachusetts native and Harvard grad (class of ’85) was just the second person in the school’s history to be twice elected president of the parody magazine The Harvard Lampoon. Right after graduation, he moved to Los Angeles and immediately began working as a writer on HBO’s groundbreaking Not Necessarily the News and later Saturday Night Live!

He also started producing, although the pilot for his first primetime show, the 1991 comedy Lookwell starring Adam West as the crime-solving former star of a TV cop show, did not go to series. (You can, however, watch it on YouTube). Disappointed in the failure of the pilot and feeling burned out after almost four years on Saturday Night Live!, he quit the show without a plan for what he would do next.

Then he got a call asking him to write for The Simpsons. He held the position of writer and producer for less than two years before getting a big break, courtesy of his old boss, SNL creator Lorne Michaels, who was also producer of The Late Show.

David Letterman had been hosting The Late Show, and Johnny Carson had practically anointed him as his successor on The Tonight Show. But the network had other plans involving Jay Leno. When Letterman discovered he was not to take over the spot, he bolted to CBS to become its late-night talk-show guy. With The Late Show slot open, Michaels decided to offer it to his pal O’Brien. O’Brien did a test show and waited to hear back.

The Simpsons producer Mike Scully remembers the day O’Brien got the call from NBC, because it was Scully’s first day on the job. The writers were at a table read, and O’Brien was seated across from Scully, and shook his hand and welcomed him to the show.

“Someone tapped him on the shoulder, and he left the room. We didn’t see him again for three days,” Scully says. “I heard on the news he had gotten the show, so I was the last person to shake his hand before he became famous.”

Scully, whose first episode was taken from an idea O’Brien pitched called “Lisa’s Rival,” says O’Brien was legendary for being brilliant and bringing a different vibe to the writers’ room.

“He was famous for not only pitching a story, but performing it, as well,” Scully says. “He would stand up and do all the character voices, and I felt like I missed out on something really special.”

“A Fidgety Marionette”

While O’Brien was widely revered as a writer, he seemed awkward on camera, with a nasally voice and odd tics; he didn’t exactly wow audiences and critics at first. NBC top brass had such little faith that they would only parcel out 13-week contracts one by one.

“I was covered in afterbirth when I first started; I just stumbled out,” O’Brien says of his shaky beginnings with exactly zero experience carrying a show. “It’s a baby deer! It’s looking into the headlights!”

He can still quote from a searing review by then-Washington Post Pulitzer-Prize winning TV critic Tom Shales that said he came off like a “fidgety marionette” and “a living collage of annoying nervous habits.”

But O’Brien, the son of a noted epidemiologist and a Boston lawyer, understood the value of hard work, setting goals and perseverance.

“I try to tell young people there aren’t any shortcuts; it’s all about having a good work ethic,” he says. “I was always a nervous kid who worked really hard and had a lot of anxiety. My parents still talk about how I always took things hard and put all of myself into anything I did.”

Few break out of the writing room to become high-profile performers, but O’Brien proved to be the exception. He threw himself into learning more about his craft.

Producer Bill Lawrence (Scrubs, Cougar Town) has nothing but praise for him. “For comedy writers, he’s our pipe dream because we sit around and say, ‘Well, if we don’t want to write for other people anymore, we can become talk show hosts,’” Lawrence jokes. “Conan used to be one of  us.”

But on a more serious note, he says O’Brien has something that few others in his line of work offer. “He’s very accessible and very much a man of the people,” Lawrence says. “Sometimes, maybe because they started as someone in the public eye, they act more like personalities and not interviewers. If you ask actors who really talks to them and allows them to engage in the most insightful interviews, they would say Conan.”

Leaving Tonight

His skills eventually paid off as his Late Show began growing both an audience and critical acclaim, even picking up an Emmy win in 2007. So when Jay Leno was nudged into a different role with a primetime show on NBC, O’Brien became the obvious successor.

But that situation brought more challenges than O’Brien could ever imagine. O’Brien was on the air only from June 1, 2009, until Jan. 22, 2010, before NBC tried to move his show to a later slot and shoehorn Leno back into the 11:35 p.m. slot after he got disastrous ratings in primetime. Rather than compromise on what he felt was a bad move, O’Brien accepted a buyout. And he left that year with a small victory: O’Brien entered his show for Emmy consideration in 2010 against the Leno version. His show landed a nomination, while Leno’s did not.

“In a good career there should be a lot of challenges,” he says. “I wouldn’t change anything that has happened to me because it has brought me to where I am today.”

And he credits his family—his parents; three brothers and two sisters; Liza, his wife of 12 years, and their young children—with keeping him grounded. “My family, they are all funny and very real, and to this day they don’t care that I’m on television. They are proud of me, but they don’t care,” O’Brien says. “And kids kick your ass every day. My toughest audience is my kids when they are eating breakfast before they go to school. I try real hard to get them to laugh and they are like, ‘Eh?’”

Hard Work Trumps Talent

While there have been people who have helped guide him at different stages of his career, including Lorne Michaels, O’Brien says the illusion when you are young that there is going to be someone “with a gray beard, who can lead you through the fog with a lantern is just a fantasy.”

“Trust me, in my 20s and early 30s I wanted that person who would explain everything to me and tell me how it’s done,” O’Brien says. “But that person doesn’t exist. Everyone has to do it for themselves. Ultimately, at the end of the day, people like Michaels taught me either you have it or you don’t.”

He says before he got his break doing The Late Show, there were “years when I felt like I put my bone marrow into a wood chipper. I just felt like I was always pushing, always working harder and harder.”

He believes that’s the reason why he’s still around after all these years. “I think I have some talent, but how much talent someone has doesn’t interest me anymore,” O’Brien says. “I used to think it was all talent, but this town is filled with talented people. The people who assiduously work and take whatever talent they have, like a little flame—you just keep blowing on it until it turns into something—that’s what interests me.”

When asked about the key to success, O’Brien’s funny-guy persona takes over.

“Denial is the key. Working out great for me. I don’t acknowledge any reality that could depress me,” he says. “I just really focus on my delusions, like I’m the best-looking man in America and a terrific athlete, and I have never been happier.”

Watch Conan O’Brien give what some critics deemed “the greatest commencement speech ever,” as he details his time of hardship and defeat with honesty, inspiration and hilarity.

Jessica Krampe is the digital managing editor for A graduate of the Missouri School of Journalism, Jessica has worked for news, entertainment, business and lifestyle publications. Outside of the daily grind, she enjoys happy hours, live music and traveling.