60 Conan O’Brien Trivia Tidbits on His 60th Birthday

Jay Leno can never take this special day away.
60 Conan O’Brien Trivia Tidbits on His 60th Birthday

Conan O’Brien turns 60 years old today, and we couldn’t be more thrilled for the legendary talk show host/anyone who holds stock in the red hair dye industry. To celebrate five decades of comedy greatness (he really phoned it in between infancy and age 10), we’ve collected 60 pieces of trivia for Hollywood’s newest sexagenarian, starting with…

He Wrote a Fan Letter to E.B. White as a Teen

While a Junior at Brookline High School, Conan sent a fan letter to Charlotte’s Web author E.B. White – and received a response, which he keeps framed in his home.

His Nose Had to be ‘Completely Rebuilt’ in High School

Conan revealed that he got a major nose job as a teen after he was severely beaten by an Italian gang for wearing a t-shirt with the Irish flag on it. When he arrived at the emergency room, he asked the doctor: “Is my nose broken?” To which the doctor replied: “Broken? Good God, man, it’s a bag of bones!”

He Was President of the Harvard Lampoon

While studying history and literature at Harvard, Conan served two terms as the president of the Harvard Lampoon, which had a profound influence on … professional wrestlers?

He Stole the Original Robin Costume From ‘Batman’

TV’s original Robin, Burt Ward, made a personal appearance at Harvard, along with his original pair of tights that left little to the imagination. Conan and a classmate pretended to be campus security as part of an elaborate scheme to steal the costume. The prank also involved a getaway car and a dude dressed up like The Penguin.

And He Once Pranked Bill Cosby

Conan also convinced Bill Cosby that he was the recipient of a prestigious lifetime achievement award from Harvard – then picked him up in his parent’s station wagon and handed him a bowling trophy. In retrospect, Cosby deserved a far harsher prank. 

He Was in an ‘80s Training Video For Music Salesmen

“This isn’t a solid spruce top!”

He Was Once Roommates With Jeff Garlin

Conan once shared a Chicago apartment with Jeff Garlin – and 18 years later, they revisited their old home with a camera crew.

His First ‘SNL’ Sketch Starred John Lithgow

The first sketch Conan pitched that actually made it to the air on Saturday Night Live starred John Lithgow as an osteology professor who’s terrified of skeletons.

He Played the Doorman of the Five-Timers Club

Conan played assorted minor roles throughout his time on SNL, including Sean, the doorman of the Five-Timers Club.

He Revisited the Five-Timers Club in 2022

Conan showed up as himself when John Mulaney was welcomed into the Five-Timers Club in 2022 (despite the fact that this joke clearly needs to die), referencing that he originally played the doorman– which, to be honest, sabotaged the foundational reality of the sketch. 

He Also Played a Random Horse Wrangler

You may also remember him as the even less memorable SNL character “horse wrangler who got bitten on the hand that one time.”

He Jokingly Threatened Mike Myers

When Mike Myers joined SNL, Conan sent him a note that began: “I’m going to destroy you.”

He Co-Wrote the Unproduced Hans and Franz Movie

Conan wrote a screenplay for a musical movie adaptation of the Hans and Franz sketch, along with Robert Smigel, Dana Carvey, and Kevin Nealon. As Nealon later revealed, the project was ultimately killed by Arnold Schwarzenegger, who was set to co-star as himself. 

Conan O’Brien’s ‘Late Night’ Audition Was Filmed on the ‘Tonight Show’ Set

After being recommended to take over Late Night following David Letterman’s departure, Conan filmed a “mock show” on the Tonight Show set with guests Mimi Rogers and Jason Alexander. 

He Co-Wrote One of the Funniest Failed TV Pilots of All-Time

Conan and Robert Smigel created the Adam West vehicle Lookwell, which sadly never made it past the pilot stage.

Conan and Andy Richter Hit it Off Immediately

As they were putting together writers for Late Night, Robert Smigel introduced his friend Andy Richter to Conan, and the two got along instantly.

He Wrote a Self-Flagellating Parody Review of His ‘Late Night’ Premiere

The day Late Night with Conan O’Brien premiered, Conan penned the hilarious article “Conan Flops!” for The New York Times, a fake review criticizing the show for the host’s use of “childish knock-knock jokes,” its sidekick (an “elderly Irish priest”) and the guests, which included “the deputy director of New York's wastewater collection bureau” and a “man who could eat oranges without getting any juice on his shirt” (which he “failed to do on camera”).

John Goodman Was His First ‘Late Night’ Guest

The first guest on Conan’s very first Late Night episode was the great John Goodman, who was presented with a 1st Guest medal by a lookalike of the Mayor …

And He Leg-Wrestled George Wendt

This was soon followed by a leg-wrestling competition between Goodman and Cheers star George Wendt. 

Paul McCartney Wrote a Song About Him (Sort of)

When Conan traveled to London to interview Paul McCartney, the ex-Beatle wrote an impromptu ditty about the host, which ominously ended with “he’s never coming back.” Not exactly “Let it Be,” Paul.

Conan Credits David Letterman with Saving His Show

Conan didn’t exactly get the warmest reception when he first started hosting Late Night, and according to Conan, he was in way over his head; NBC made it clear that he “wouldn’t be around very long.” But then the “miraculous” happened: Conan’s predecessor, David Letterman, asked to be a guest on the show – which had a “profound impact.” Conan later said that because of that show: “everything turned around for me.”

He Met His Wife Liza While Taping ‘Late Night’

Conan married his wife, Liza Powel O’Brien, in 2002; they first met after he noticed her while taping a segment of his show in 2000. “Somewhere, in the vault at NBC, there's footage of me literally falling for my wife on camera," he later said. 

He Once Went Apple Picking with Mr. T

“You put the fear of god into this apple.”

But He Played a Joke Version of the Show on ‘Late Night’

Conan was still able to drop by the set to film a sketch with Regis Philbin

He Turned Old Episodes of ‘Walker, Texas Ranger’ Into Comic Gold

The Walker, Texas Ranger Lever was created after NBC merged with Universal, and Conan suddenly had the rights to a seemingly bottomless well of ridiculous Chuck Norris clips. They had to shut the bit down once actors began asking for residuals, and it became too pricey.

He Predicted The Future of ‘Indiana Jones’

When Harrison Ford first appeared on Late Night in 2000, Conan prophetically speculated that they could keep making Indiana Jones movies well into Ford’s old age: “When you’re 80, you could do one where they just bring the treasures to you.”

Jim Carrey Played Conan in a Fake Biopic

“I can’t hear the laughter anymore…”

NBC Tried to Ban Norm MacDonald From ‘Late Night’ – But Conan Stood Up For Him

After Norm Macdonald was fired from Saturday Night Live for relentlessly making O.J. jokes, NBC executive (and O.J.’s buddy) Don Ohlmeyer wanted Late Night to ban him from the show. Despite Ohlmeyer having suggested Conan for the job and Conan's sense of loyalty towards him, the show continued to book Norm, with Conan telling Ohlymeyer: “You've hired me to do the best show I can do, and this is my best guest.”

Things Got Real Weird/Amazing During the 2007 Writers’ Strike

Late Night was off the air for nearly two months during the writers’ strike, which began in November 2007 and stretched into 2008. When Conan returned, he had a beard but no writers – which meant relying on frequently anarchic new bits such as “German Disco Lightshow”...

… and “Ziplining to Save President Lincoln.”

His Meeting with Bob Dylan was Ruined by Al Gore

Conan got to go backstage at a Bob Dylan concert, but as he finally got to meet the legend, the moment was immediately ruined by former Vice President Al Gore

He’s Not a Bad Guitar Player

Conan has jammed with legends like Bruce Springsteen and David Bowie.

He Was in a White Stripes Music Video

Much of The White Stripes’ video for “The Denial Twist” took place on a mock-up of the Late Night set.  

He Hosted ‘SNL’ in 2001

Conan hosted SNL in 2001 but joked on his show that they were using the “second string cast” for the episode, made up of a bunch of nobodies, plus Tracy Morgan

His First Show After 9/11 Opened with a Somber, Thoughtful Monologue

“I make a living acting like an ass, generally … no one’s looking to me to put this in perspective.”

Conan’s First ‘Tonight Show’ Began With Him Jogging Across the Country

When Conan “inherited” The Tonight Show from human barnacle Jay Leno, the opening to the first episode found him jogging across the country, through Wrigley Field, past the Gateway Arch, stopping only briefly at a Victorian Doll Museum.

His First (and Last) ‘Tonight Show’ Guest Was Will Ferrell

Conan opened his Tonight Show run with Will Ferrell, who also appeared on Conan’s final Late Night show. Ferrell did a bit pretending that he thought it was probably his last show because studio executives could “pull the plug at any second.” Ferrell eventually came back for Conan’s last Tonight Show as well. 

Conan’s Final ‘Tonight Show’ Scored His Best Ratings

Conan scored huge ratings in his final Tonight Show episode, telling audiences: “Walking away from The Tonight Show is the hardest thing I have ever had to do.”

Tom Hanks Popularized the Nickname ‘Coco’

“You ruined my life,” Conan told Hanks

He Didn’t Take Any Money From the Tour and Used it All to Pay His Staff

According to reports, Conan used the tour money to pay his staff – or, as TMZ so eloquently put it, “No Bread for the Redhead.”

He Was on an Episode of ‘Inside the Actor’s Studio’

Despite not being known for his thespianism, Conan was the guest for a 2009 episode of Inside the Actor’s Studio

Before That, Host James Lipton Was on Conan’s Show

James Lipton had previously appeared on Late Night, where he shotgunned a beer to celebrate spring break. 

He Had a Custom Superhero Suit Made For Comic-Con

Conan commissioned Ironhead Studio to make him his very own superhero costume for a series of shows at San Diego Comic-Con. 

He Tapped Ralph Macchio to Make Jordan Schlansky Look Like an Idiot

You can practically hear Conan associate producer Jordan Schlansky’s soul collapsing in on itself as his Karate Kid fandom is called into question by Daniel LaRusso himself. 

He Performed the Monorail Song at the Hollywood Bowl

“There's nothin' on Earth like a genuine, bonafide, electrified six-car monorail!”

Will Ferrell Zoomed In For His Final TBS Show

Will Ferrell returned, via Zoom, for yet another Conan O’Brien finale.

Conan Appeared as Himself in an Episode of Will Arnett’s ‘Murderville’

“She’s dead. She’s SO dead.”

He Impersonated Andy Warhol in ‘Weird’

Conan played legendary artist Andy Warhol in Weird: The Al Yankovic Storythen forgot all about it until the movie came out.

He Made a $150 Million Podcast Deal

While many podcasters are still shilling food boxes and mail-order underpants just to pay the bills, Conan sold his “podcast and digital media business” to SiriusXM for a whopping $150 million. 

You (yes, you) should follow JM on Twitter (if it still exists by the time you’re reading this). 

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