Stephen Colbert may be one of the most beloved men on late night television, but the path there wasn’t always easy.
From an early childhood marked by a life-changing tragedy, to struggling to find work in Chicago, to “learning to love the bomb” and finally arriving on — and dominating — late night television, Colbert has led a fascinating life.
Here’s a five-minute look at how Colbert made it from South Carolina to New York City and amassed a fortune.
Stephen Colbert was born on May 13, 1964 in Washington, D.C., although he mainly grew up on James Island and in downtown Charleston, South Carolina.
He was born to a huge, devout Catholic family, and was one of 11 brothers and sisters. His father, James William Colbert Jr., was a doctor specializing in immunization and the vice president of a local medical school, while his mother was a homemaker.
If you ever notice Colbert straining to hear a guest, it’s because he can’t hear in his right ear. As a kid, there was something wrong with his ear, so “they scooped it all out with a melon baller,” as he once told David Letterman.
He’s probably kidding. Maybe?
The surgery also put a lid on his youthful aspirations to become a marine biologist, since he wouldn’t be able to scuba dive.
Everything about Colbert and his family changed on September 11, 1974, when Eastern Air Lines Flight 212, attempting to land in dense fog, crashed three miles short of a runway in Charlotte. Seventy-two people were killed, including Stephen’s father and two brothers, Peter and Paul. Stephen was 10 years old.
His mother relocated the family from James Island to downtown Charlotte. Separated from his childhood friends and feeling disassociated with the world, Stephen buried himself in science fiction and fantasy novels and picked up Dungeons and Dragons (he played a witch).
“Nothing made any sense after my father and my brothers died. I kind of just shut off,” he told The Post and Courier.
While Colbert does come from a huge family, it was mostly just him and his mom after the plane crash. The rest of his siblings were significantly older and off to school or had moved out (Peter and Paul were closest to him in age). So he used comedy to help cope, both in school to make friends, and at home to keep his mother happy.
“I was there with my mom, she was there for me, and I sort of kept her going,” Colbert told Howard Stern.
In turn, his mother taught her son how not to let tragedy leach the joy out of life. “And by her example am I not bitter. By her example. She was not. Broken, yes. Bitter, no,” he told GQ.
He graduated high school with a litany of extracurricular activities. Check out his yearbook page.
After spending two years at Hampden-Sydney College in Virginia, Colbert transferred to Northwestern University in Evanston, Illinois.
There, he completed a three-year acting program in two years and worked two student jobs: one in the cafeteria line and one doing computer data correction.
After graduating, he headed to Chicago.
In Chicago, Colbert applied for a graduate program in drama at a school in New York, but decided to hang around the city for a while and pursue acting gigs instead. One year later, he applied to the same school once again.
They turned him down.
“I was like, ‘Oooh, I have ruined my life.’ And right then is when I started to improvise,” he said, according to the Chicago Reader.
And by improvise, he meant it literally. Colbert attended Second City, a famous Chicago improv group where he worked alongside Chris Farley, Steve Carell and Amy Sedaris.
While living in Chicago, Colbert picked up odd jobs to make ends meet. One job was waiting tables.
“Everybody should do it to see what it’s like to serve someone else, and not be able to answer in kind when someone is unkind to you,” he told Oprah.
As for advice for patrons? “Whatever you’re gonna give ‘em, give ‘em one more dollar. It’ll make ‘em so happy! It’s nothing to you! One dollar, that’s nothing to you, but it’ll make their day.”
And he speaks from experience. He said the most he ever made in a week at the now-shuttered restaurant called Scoozi was $250.
If you’ve ever wondered how Colbert learned to be fearless, it’s because of this advice. During his time at Second City, director Jeff Michalski told his students: “You have to learn to love the bomb.”
Meaning, you had to embrace it when you fail. You had to literally start enjoying it.
“You gotta learn to love when you’re failing…The embracing of that, the discomfort of failing in front of an audience, leads you to penetrate through the fear that blinds you,” Colbert told GQ.
Colbert said he would sometimes do intentionally embarrassing things, like singing in an elevator. “The feeling you feel is almost like a vapor,” he said in GQ. “The discomfort and the wishing that it would end that comes around you. I would do things like that and just breathe it in.”
Sometime in 1990, Colbert had been dating a woman for a few years when she basically gave him an ultimatum to get married.
Colbert took some time to think about it and went back to Charleston to visit family. After attending a play, he spotted a girl that he thought he never saw before and starting chatting her up.
Turns out, they had grown up together. Which was embarrassing at first, but they fell in love and married in 1993. Watch his in-depth tale about getting together with Evelyn McGee-Colbert.
After about eight years in Chicago, Colbert — who never went back for that graduate degree — headed to New York City for a 1995 sketch show on Comedy Central called “Exit 57,” which starred several other Second City vets.
The show only had 12 episodes, but received favorable reviews. Colbert also co-created and starred in the cult classic show “Strangers with Candy,” also on Comedy Central. In 1996, he worked on “The Dana Carvey Show,” but that was a short-lived and spectacular failure.
Colbert was hard up for cash.
“I had been working for ABC at ‘The Dana Carvey Show’ in 1996. That show got canceled, my wife wasn’t working, and we had a baby. I desperately needed a job,” Colbert told Vanity Fair.
He even went, very briefly, into real news as a correspondent for “Good Morning America,” where he did two reports. Only one of them aired. Then his agent referred him to a pseudo-news program on Comedy Central called “The Daily Show.”
Colbert actually got to the “The Daily Show” during Craig Kilborn’s second season, well before Jon Stewart. And he didn’t expect it to last.
“They had me on for a trial basis, and for the next nine months I worked at ‘The Daily Show’ occasionally, during Craig Kilborn’s second year. But it was totally a day job. I never expected to stay, because I did sketch comedy and I wrote, and I really didn’t think that [it] was going to go anyplace,” Colbert told Vanity Fair.
Colbert actually auditioned for the host of “The Daily Show” after Craig Kilborn left in late 1998, but ended up back in a correspondent position with Jon Stewart at the helm. The two hit it off, and the show itself gradually picked up steam.