Conan O’Brien isn’t just another late-night talk show host. He’s a writer, comedian, producer, and one of the most recognizable redheads in entertainment. From humble beginnings as a writer for The Simpsons and Saturday Night Live, Conan worked his way into becoming a household name. His self-deprecating humor, quick wit, and smart delivery have made him a fan favorite for decades.
Here are some lesser-known and entertaining facts about Conan O’Brien that show a different side of this brilliant funnyman.
1. From Harvard to Hollywood
Conan comes from an accomplished family. His father is a professor at Harvard Medical School, and his mother is a lawyer. Not surprisingly, Conan was a top student. He graduated magna cum laude from Harvard University with a degree in history and literature. At Harvard, he was the president of The Harvard Lampoon, where he honed his comedic writing skills.
2. He Was a Prankster at Harvard
Despite his academic achievements, Conan had a mischievous streak. One famous incident involved him orchestrating a fake theft of actor Burt Ward’s Robin cape during a college event. Dressed as security guards, Conan and his friends staged a “heist” mid-speech. Thankfully, Ward had a sense of humor and got his cape back later that day.
3. He Wrote for SNL and The Simpsons
Before becoming a host, Conan made his mark as a writer. He worked for Saturday Night Live from 1988 to 1991. After leaving SNL, he joined the writing team for The Simpsons and created some of its most memorable episodes, including “Marge vs. the Monorail.” His time on The Simpsons became a key part of his legacy in television.
4. Nervous Writer Gags
During writing sessions, Conan sometimes made up characters to make the room laugh. One of them was “Nervous Writer,” who would nervously try to drink Diet Coke but spill it everywhere. These antics earned him a reputation as both clever and unpredictable in the writers’ room.
5. From Unknown to Late-Night Legend
When David Letterman left Late Night, NBC took a chance by naming Conan as his replacement. The network wasn’t confident. They only gave him a short contract and quietly searched for a backup host. But Conan beat the odds. He found his rhythm and hosted Late Night with Conan O’Brien for 16 years.
6. The Tonight Show Controversy
In 2009, Conan became the host of The Tonight Show, taking over from Jay Leno. But within a year, NBC decided to move Leno back into the slot, pushing Conan out. He refused to move the show to a later time and left the network in early 2010.
NBC paid Conan $45 million to walk away from The Tonight Show. Out of that sum, Conan paid six weeks of severance to about 50 staffers who were not covered by the deal. His generosity earned widespread respect.
7. A New Chapter on TBS
Later in 2010, Conan returned to late night with a new show on TBS, simply called Conan. This allowed him more creative freedom and a younger audience. The show ran until 2021 and featured remote travel segments, unscripted moments, and offbeat humor.
8. Yes, He Was Stalked
In 2006, a Roman Catholic priest named David Ajemian began stalking Conan after being denied a seat in the show’s audience. Ajemian sent threatening letters signed “Your Priest Stalker” and even contacted Conan’s parents. He was eventually arrested while trying to enter NBC studios.
9. Conan the Officiant
In 2011, Conan became an ordained minister through the Universal Life Church. He did this to perform a same-sex wedding for a staff member on-air. The ceremony was legal and took place in New York. It was one of the earliest same-sex weddings ever shown on late-night TV.
10. He’s a Family Man
Conan met his wife, Liza Powel, while filming a comedy sketch at the ad agency where she worked. The couple married in 2002 and have two children. Despite his wild on-screen antics, Conan keeps a low-key and private family life.
11. His Influence Runs Deep
Many comedians and actors got their start with Conan. Bob Odenkirk (of Breaking Bad and Better Call Saul), Louis CK, and John Krasinski (of The Office) all worked for or were discovered by Conan early in their careers.
12. He Was a “Late Bloomer” Host
Conan was 46 when he took over The Tonight Show, making him the oldest person to become the new host of the iconic program. That didn’t stop him from bringing a fresh take, even if his tenure was short.
13. Fans Call Him “Coco”
Actor Tom Hanks gave Conan the nickname “Coco” during a guest appearance. Though Conan hated it at first, the name stuck, and fans started using it endearingly.
14. He Traveled to Cuba
In 2015, Conan filmed an episode of his show in Havana, Cuba. He became the first American late-night host to shoot a full episode in Cuba since Jack Paar in 1959. The visit included skits, street interviews, and cultural exchanges.
15. Celebrity Interviews and Oddball Moments
Some of the most famous Conan guests over the years include David Bowie, Tom Hanks, Jim Carrey, and Jack Black. But the show was also known for quirky guests and skits, like the recurring Claymation episode or the “Walker Texas Ranger Lever.”
16. He Once Auditioned at Jay Leno’s Set
Before getting Late Night, Conan had to audition — and it happened on the set of The Tonight Show with Jay Leno. He impressed NBC enough to land the job over big names like Jon Stewart and Drew Carey.
17. A Touch of Gonzo
Conan once tried to get legendary writer Hunter S. Thompson to guest on his show. Thompson agreed only if they filmed a segment at his upstate New York farm that involved guns and hard liquor. Conan agreed. The result was a bizarre and memorable segment featuring machine guns and whiskey.
18. He Has a “Different” Nose
Conan’s nose is not original — not by choice. While in high school, he was assaulted by a street gang. The injury required reconstructive surgery. He shared this in an interview with Marc Maron, showing how not all funny men have had easy lives.
19. He Was the Valedictorian
In high school, Conan was class valedictorian and the managing editor of the school newspaper. His academic record was spotless, making his turn into comedy writing even more interesting.
20. The Simpsons Saved His Career
After leaving Saturday Night Live, Conan had no job offers. He wandered New York without a plan. Then he got a call from The Simpsons, offering him a writing role. He later said the job “saved his professional life.”
Conclusion
Conan O’Brien’s path from Harvard prankster to late-night legend is one filled with ambition, risk, and a lot of laughter. His success didn’t happen overnight, but it was well-earned through creativity and perseverance. These fun facts not only make him more relatable but also highlight how unique his journey really is.
Whether you know him as a former writer, late-night host, or “Coco,” one thing’s for sure: Conan O’Brien is one of the most influential comedic voices of his generation.