Conan O’Brien’s Worst ‘Late Night’ Guest Is Surprising

Conan O’Brien has an impressive career in late-night television. The always amusing, wise-cracking host has been a favorite since the early ’90s when he first made the leap into the spotlight. 

Recently, the gifted comedian announced that his beloved series, Conan, would be coming to a close. Fans will have to catch him on HBO Max now, where he will be hosting a weekly variety show. It’s sure to be a hit, with fantastic celebrity guests and loads of O’Brien’s wacky humor. Speaking of celebrities, the host says there is one interview that was especially memorable…

Conan O'Brien smiling in front of a black background
Conan O’Brien | Kevin Mazur/Getty Images

Conan O’Brien: The early years

The gangly, goofy, red-haired Conan O’Brien has captivated late-night audiences for nearly 30 years. It is absolutely impossible to watch the charismatic late-night host without cracking a smile–and more likely–busting a gut. Everything about the man is downright hilarious, from the way he interacts with his constant sidekick, Andy Richter, to the way he sometimes just stares at the camera saying nothing at all. 

According to Britannica, O’Brien hails from a large family. He grew up in Massachusetts with five siblings, so he had plenty of people to entertain even when he was a kid. The comedian was always interested in making people laugh, and even wrote funny plays as a child. 

The late-night host is brilliant as well as funny. He graduated magna cum laude from Harvard, where he was president of the school’s humor magazine, The Harvard Lampoon. After leaving Harvard, O’Brien landed a job with the writing team for the HBO series, Not Necessarily the News

Now that he was in L.A., O’Brien found many new opportunities to perfect his art. He worked with several improv groups and continued writing for HBO. His big break came in 1988 when he became a writer for Saturday Night Live. Popular skits such as “Mr. Short-Term Memory” and “Girl Watchers” earned SNL writers an Emmy Award in 1989. 

In 1991, O’Brien left SNL and began writing for another comic gem, The Simpsons. His unique sense of humor and innovative ideas earned him a supervising producer role shortly after he began working with the popular series. 

He’s been making late nights funny since the ’90s

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In 1993, O’Brien stepped into the spotlight when NBC hired him to take David Letterman’s place. Late Night with Conan O’Brien wasn’t exactly a hit at first, as the host’s inexperience and nerves definitely showed in the first few episodes. However, O’Brien didn’t take long to get comfortable, and soon had a loyal following of late-night fans. 

Fans loved the combination of a classic late-night show with the comedic relief of bits like “Clutch Cargo.” In “Clutch Cargo,” O’Brien would “interview” celebrities, whose faces were used with fake lips and dubbed comments. Several famous faces were used in the bit, like Tom Cruise, Bill Clinton, and Arnold Schwarzenegger. The show won an Emmy in 2007.

Late Night with Conan O’Brien ran until 2009 when the host took over for Jay Leno on The Tonight Show. Longtime friend Andy Richter once again joined O’Brien’s team, but the show didn’t do too well. A lot of drama ensued, with Leno and O’Brien taking public digs at each other as well as at NBC. Leno eventually returned to the show until 2014, when Jimmy Fallon replaced him. 

After a brief live tour in 2010, O’Brien returned to the late-night scene with a new show on TBS, simply titled Conan. In addition to his incredible late-night career, O’Brien has appeared in numerous television shows and movies. 

Who was O’Brien’s worst guest ever?

Any talk show host with a career as long as O’Brien’s is bound to have a few tough interviews along the way. Some celebrities are uncooperative while others are super spoiled. Then there are some who are just plain off-their-rockers.

In a 2018 interview on the podcast Armchair Expert with Dax Shepard, O’Brien said that one of his worst guests of all time was director Abel Ferrara. Apparently, Ferrara actually fled the scene, running out of the building and down the street in an attempt to skip his appearance on Late Night. One of the show’s producers chased him down and dragged him back to the set. 

The insanity continued as Ferrara made it quite clear that he was doing this interview against his will. He sat slumped over in his chair the entire time, poking at his face with an unlit cigarette and avoiding eye contact with anyone. He mumbled incoherent answers to O’Brien’s questions, to which the host once remarked, “I want to get those Stallone subtitles in here.” 

O’Brien, per usual, handled the awkward encounter like a champ. He now refers to the experience with fondness, calling it “a fantastic, crazy, strange moment.” The interview has gone down as one of the most memorable segments on Late Night with Conan O’Brien.