Conan O’Brien: From Unknown to Late Night Legend
On September 13, 1993, a young, virtually unknown former Saturday Night Live and Simpson’s writer strolled through the streets of Manhattan to jeers of “Better be as good as Letterman.” You now know that writer as talk show and podcasting legend Conan O’Brien, but those first few years were rocky. Everyone unanimously agreed he wasn’t as good as Letterman and Conan has stated he felt like a national punchline at 30.
Since most late night talk shows don’t receive full episode releases due to copyright issues with movie clips and musical performances, the only nearly complete document we have from Conan’s early struggle is his first episode on NBC. And even that is missing the movie clips. As Conan and Mr. T attested on the Late Night With Conan O’Brien 10th Anniversary Special, Conan was on TV for 10 years, but was only funny for 7 of them.
To be fair, Late Night with Conan O’Brien’s debut was awkward. Conan was obviously green, yet that doesn’t make it bad. However, the pressure NBCU was applying to the Late Night staff — particularly Conan — was palpable. Conan mined it for as many laughs as he could with an opening sketch that intentionally draws as much attention as possible to his situation with a fictitious New York Post headline stating “Conan Better Be Good” and Tom Brokaw ominously welcoming him to NBC. When Conan struggled to hide his fear that his dream job may not work out, he outright stated NBC has a lot riding on his success.
It is impossible to look at Conan’s first episode from the perspective of someone inviting him into their house for the first time. NBC’s lack of confidence is well documented in multiple 13 week contracts with Conan and NBC’s panicked attempt to find a replacement that kept coming up short. Hence, Late Night with Conan O’Brien kept getting stays of execution.
Looking back, it is clear why NBC had no faith in the show and it was always on the verge of cancellation. With the benefit of hindsight, it’s also easy to see the glimmers of what was to come as long as Conan was given a chance to succeed. The foundation was shaky, yet already in place. Andy Ritcher was the sidekick. The Max Weinberg 7 were playing as tight as ever. Joel Goddard, who would announce Late Night with Conan O’Brien for its entire run, was already participating in skits. Granted, handing Conan a flower is a long way off from appearing in several skits where Goddard has a weird perversion for scantily clad, young, Asian men and Weinberg had yet to establish his own perverted comic persona.
The monologue is the most painful part to look at because Conan’s nerves got the best of him. It’s also odd to see him come on stage and look right into the camera and stay completely still. There is no jumping, turning, string dance, or weird nipple rubbing that became a staple on Conan’s TBS show.
Throughout the monologue, you can’t help but wonder “Is he chewing gum?” Considering, we know Conan chewed gum before the show because he had forgotten to spit it out before going live-to-tape, it’s entirely possible. His other nervous habits included constantly playing with his watch, licking his lips, and awkward movements with his hands. It’s likely that Conan knew his tics would be noticeable, since there is a bit about trying out signature gestures.
It probably didn’t help that the entire monologue was dedicated to his “45 seconds” in show business and jokes about his anxiousness. Despite not being notable at the time, Conan’s joke about how he wants to “start on TV and claw my way into clubs” now feels like unintentional foreshadowing to the Legally Prohibited on Television Tour.
While Conan never stopped jumping up and down or nervously rubbing his hands together, with experience he was able to make them part of the show, such as when he would get the audience to join in on “I’m a gonna go to Hell when I die” after a questionable joke, rather than a distraction.
For the pre-interview desk sketch, Conan and Andy present Small Town Items, which has always been the more absurd interpretation of Letterman’s Small Town News or Leno’s Headlines. Longtime fans know it better as Actual Items, but it’s always been true that “you can’t make this stuff up” and it is definitely not “faked and doctored by a graphics department.”
The guests on Conan’s first show were John Goodman, Drew Barrymore, and Tony Randall, who were all willing to work with the first-time talk show host. While the conversations were typical talk show banter, Goodman and Randall participated in bits. John Goodman, who was promoting Roseanne and The Flintstones movie, was part of three: receiving the first guest medal, being told he was voted the celebrity who most looks like Mr. Potato Head, and leg wrestling with George Wendt. During the Mr. Potato Head bit Conan would use the opportunity to point out he looks like Raggedy Andy; with time his references would be updated to Alf and Jimmy Neutron.
Between Goodman and Barrymore, Conan announces that the show would return after this special effects technician. It doesn’t make any more sense in context, yet it is the first example of a random character that serves no real purpose. Special effects technician may not be in the pantheon of best random Late Night characters, but he is the predecessor to Vomiting Kermit, Masturbating Bear, FedEx Pope, and all the other characters who appear on the show simply to be random.
There is also a promo for Later with Bob Costas that is actually a bit where he interviews “the two surviving cast members of the Wizard of Oz: one of the Munchkins and a tree. (More cast members were alive at the time, but I probably shouldn’t explain the bit.)
Drew Barrymore was the second guest of the night. Officially, she was promoting The Amy Fisher Story, but she also mentions shooting an unnamed western — most likely Bad Girls — in Brackettville, Texas. This is far from her most memorable late night appearance, after all, this is the woman who flashed David Letterman for his birthday. Throughout the interview, Conan brings up Barrymore’s Guess ad and her tattoos in a way that he would never get away with in 2024.
The final guest was Tony Randall, who was either promoting the TV movie The Odd Couple Together Again or Fatal Instinct, and came dressed ready for a black tie affair. Like he did as a guest on Password, Randall acted above the show on which he voluntarily appeared on with snipes at Conan’s suit, the leg wrestling, the Joe Franklin picture on the wall, and Conan’s comedy in general. Between the jabs, Randall did manage to give Conan a good piece of advice: “Don’t pander. You must stick to your artistic conscience, such as it is, and do what amuses you.”
After a monologue, a few bits, and three interviews, Conan makes it to the end of his show where he is his own musical guest. Conan comments on his “beautiful singing voice” and that he is going to single “this simple lullaby for those going off to sleep.” He sang “Edelweiss.” The entire sketch exists to showcase a crying nun, a crying Nazi, and Tony Randall’s singing voice.
The show ends with Conan saying “We’ll see you” rather than the “Goodbye, everybody goodbye” that would become his signature parting phrase on Late Night. Weirdly, Conan comes into his own during the closing credits when the “End of the Show Song” is played as he dances in a manner Conan himself has described as “inflatable guy on a used car lot.”
As the credits roll, viewers can spot the future who’s who of comedy. The writers’ room was stacked with Louis CK, Bob Odenkirk, head writer Robert Smigel and other less visible names writers like David Reynolds who would go on to work for Disney and Pixar.
The first episode of Late Night with Conan O’Brien is definitely funnier in hindsight than it would’ve been at the time. With the benefit of hindsight, fans can appreciate the mostly unseen moon in the background’s uncanny resemblance to the Conan moon that could be controlled and was known for its “lunar wobble.” Also, eagle-eyed viewers will notice Ernie Kovacs and Tom Snyder or on the wall behind Conan, Andy, and guests. On Conan’s later, less claustrophobic sets those photos would be replaced with a wall that had four photos: Steve Allen, Jack Paar, Johnny Carson and David Letterman. After 30 years, it is not hard to imagine a future late night host adding Conan O’Brien as a fifth photo on that wall.
