Thirty Years Later, Was Conan O’Brien’s First Show As Host of ‘Late Night’ Really That Bad?

Thirty years ago today, Conan O’Brien hosted his first episode of Late Night, stepping up as the unlikely successor of comedy royalty David Letterman. This momentous occasion began the decades-long process of the late-night watching public falling in love with the lanky ginger and out of love with Jay Leno.

Conan had easily the most improbable success story of any late-night host to ever spend over a quarter of a century on the air. As opposed to the Lenos and the Lettermans of the era, Conan was not a tried-and-tested stand-up capable of winning over any audience, in-studio or in a club. The 6-foot-4, Massachusetts-born Irish-American was, instead, an accomplished TV writer coming off of a successful stint on The Simpsons, where he wrote iconic episodes like “Marge vs. The Monorail” and “Treehouse of Horror IV.” He was a Harvard yuppie with just a small handful of on-screen credits who was handed the dubious honor of replacing the late-night host most considered to be TV’s best. Much like Ireland itself, Conan was green.

Looking back exactly three decades after Conan’s late-night career began, it’s hard to imagine any alternate timeline where things shake out better for the shaking, eager and endlessly enthusiastic 30-year-old who, astoundingly, chose to launch the new Late Night with a leg-wrestling match between John Goodman and George Wendt. Here is the first episode of Late Night with Conan O’Brien in all its early 1990s glory:

The pilot starts on a strong note. In an extended lead-in, Conan skips across New York City, shrugging off comments from passersby that there’s “a lot of pressure” on him and ignoring vague threats from Tom Brokaw that “you better be as good as Letterman — or else.” Conan enters his dressing room and, while whistling, loops a noose over the ceiling fan and prepares to slip his head through it before a crew member calls him to the set.

An awkwardly long and obviously unearned applause precedes Conan’s first opening monologue, which he acknowledges along with his inexperience, saying, “I’ve been in showbusiness for 45 seconds, and this is the nicest reception I’ve ever had!” Conan further plays on NBC’s nontraditional casting choice for the hosting gig, pointing out that he’s living the stand-up comic’s dream in reverse: “My plan is to start on TV, then claw my way into the clubs. Ten years from now I want to be in high school!”

Conan closes out the monologue, delivered with all the eagerness and visible preparation of a theater kid in a high school audition room, by recalling a story of how he told his friends back during his teen years that his dream was to host a talk show, to which they supposedly replied, “O’Brien, the day you get your own talk show is the day there’s peace in the Middle East!”

After the monologue, Conan and his soon-to-be longtime sidekick Andy Richter engage in some scripted banter, breezing through a segment called “Actual Small Town Items” in which the two pretend that fabricated clippings from local newspapers are actual finds from their research department. Conan incredulously shows off an “ad” from a “mini golf course” which reads, “We are a really bad miniature golf course. You shouldn’t come here.”

Goodman joins the show as its first guest, showing himself to be a legendarily good sport when Conan parades him in front of a crowd of “paparazzi” and hangs a medal around his neck which reads, “1st Guest.” Goodman cracks about the award, “In a couple of years when I bottom out I can trade this for a bottle of cheap scotch.” The two go through some pre-planned, surface-level patter about the movie Goodman is promoting (the live-action Flintsones film) before challenging anyone in the studio to “leg wrestle” with the guest. Cheers star George Wendt stands up from the audience and accepts the offer, and the show cuts to commercial as the two burly beloved actors writhe on the floor.

Past this point, the show visibly falls apart. Conan interviews future talk show host Drew Barrymore in a less controlled conversation that adds next to no entertainment value, then an elderly Tony Randall dressed in a tight tuxedo takes the seat next to the host as he and Conan engage in some rehearsed banter about Conan’s clothing choices, with the only seemingly organic moment occurring when Conan flubs a line and says to his guest, “You’re not amused by me at all, are you?”

The show ends with a song as Conan sings “Edelweiss” from The Sound of Music as nuns and SS officers in the audience are moved to tears. Roll credits. First one in the books.

Overall, Conan’s first Late Night experience was nervously energetic but surprisingly stiff. NBC didn’t demonstrate a great deal of faith in their new hire by scripting the entire night down to every utterance and awkward pause, and most of the memorable jokes came from anyone but Conan himself. Still, Conan’s charisma and excitement shined through in those few meaningful moments that foretold how his audience and NBC itself would learn to love his weirdness, his earnestness and the sheer spastic spectacle of his stage presence. 

At least it went better than his stint on The Tonight Show.