What The First Episode Of Late Night With Conan O'Brien Was Like

Late night fans of a certain age may find it hard to imagine a time when Conan O'Brien was not one of the funniest people on television. Conan has stood out from other late-night talk show hosts both physically (thanks to his tall build and red hair) and comedically. He might have worn the same suits and followed the standard structure as other hosts at first, but Conan O'Brien did things his way and television is better for it.

For nearly 30 years, O'Brien has hosted shows on two different networks, traveled the world, launched a successful podcast called "Conan O'Brien Needs a Friend," and struck a development deal with HBO Max (via Deadline). He has paved his own path, leaving behind an incredible comic legacy. However, there was a time when audiences didn't know his name and were uneasy with him as David Letterman's "Late Night" replacement.

In 1993, O'Brien was just a funny writer from "Saturday Night Live" and "The Simpsons" with little experience in front of the camera. He was plucked from obscurity by the wise hands of producer Lorne Michaels and thrown into the deep end of nightly television production. He could have easily buckled under the pressure. Instead, he showed America he had what it takes to keep us laughing for decades. As proof of this, we're looking back at the first episode of "Late Night with Conan O'Brien" to see how well it holds up and what kind of performer Conan was at the beginning.

When Johnny Carson decided to retire as host of "The Tonight Show," a small war broke out between comedian Jay Leno, who often hosted the show in Carson's absence, and David Letterman. The latter was the host of "Late Night with David Letterman," an irreverent talk show which aired immediately following Johnny Carson and was naturally considered to be Carson's successor. The network hired Leno, though, and Letterman decided he would leave NBC for CBS, leaving his hosting seat vacant.

On the June 24, 2022, episode of the podcast "Inside Conan," producer Jeff Ross and Conan O'Brien discuss their experiences getting hired for "Late Night." NBC put Lorne Michaels in charge of producing "Late Night" and finding a new host. He initially offered Conan the job of head writer, but he turned it down. When Lorne then asked him to host, he took the advice of writer Robert Smigel's wife and went for it.

Why Lorne thought he was the man for the job is unclear. Conan wasn't a TV personality, he was just a writer. Still, Lorne thought he could do it, and Conan dove in. After a successful audition, it was between Conan and Garry Shandling (who was currently satirizing late-night shows on "The Larry Sanders Show"). When Shandling declined, the job went to Conan, and he had to step into the giant shoes of a beloved television personality who was already considered a living comedy legend. No pressure, though.

It's important to have someone that the host of a late-night show can play off. It gives them a chance to sit back, banter, and appear casual while they do some comedy bits from behind a desk. First, there was Johnny Carson and Ed McMahon, later David Letterman famously played off of band leader Paul Shaffer, and now Conan O'Brien had Andy Richter. The two worked together like jazz musicians, knowing exactly when to set the other one up and when to stand back to let them do their thing.

Although they joke about knowing each other for years, Conan actually met Andy while he was still figuring out the show. Andy Richter told Rolling Stone that Robert Smigel offered to introduce him to Conan while at a party at Bob Odenkirk's house. The pair met up at a diner and hit it off. "We met and immediately, like, I knew I could be as stupid as I want to be with him and he loved it."

On his podcast "Conan O'Brien Needs a Friend" Conan relayed how enthusiastic he was after meeting Andy. "I thought, 'We've gotta get this guy on the show.'" He told that to Smigel (who was the head writer on the show). Smigel suggested they look at Andy's comedy material first. After hearing this, Conan says, "I remember thinking, 'I don't care about his packet. He's just really so funny.'" Richter became the co-host and their dynamic blossomed.

In case you needed reminding just how much people loved David Letterman on "Late Night," the cold open to Conan's first episode has you covered. It begins with a bright-eyed and optimistic Conan waking up to a beautiful New York City morning. He goes about his routine without a care in the world, even though the television and almost every single person he passes on the street says that he'd better be as good as Letterman while pointing out the kind of pressure he's under.

The funniest moment is when news anchor Tom Brokaw threatens to crush Conan like a bunch of saltines if he's not as good as Letterman. Conan then visits his dressing room (the door doesn't even have his name on it) and gets ready for the show. However, it starts to look like the optimism was all a facade as Conan slides his head into a noose. At the last second, he's informed that it's time to go on, and he decides to postpone ending his life to do the show.

This bit sets up the tone and theme for the episode quite nicely. It is cartoonishly silly (a staple of Conan's comedy) in its depiction of the entire world expecting him to fail, proving that Conan is well aware that he has no business hosting a television show. This will carry on through the rest of the episode as Conan never misses an opportunity to point out the absurdity of his situation.

The opening monologue is akin to a standup set by a comedian. The host steps out from behind a curtain and tells jokes to the audience. Often times the monologue is used to address the news of the day. It's a time when the audience gets a little solace from all the negativity being reported by watching their favorite TV host make fun of all of society's "important" people, like politicians and celebrities.

For Conan's first monologue the biggest story he can talk about is the fact that he has no experience with this kind of job. As he says, "A lot of guys, they spend years and years in the clubs working very hard, struggling. And finally, they get here on television." That wasn't his journey at all. So, he jokes, "My plan is to start on TV, claw my way into the clubs — ten years from now, I want to be in high school."

The fascinating thing about this monologue all these years later is how much it feels like a traditional Conan monologue. He's clearly nervous (as evidenced by continuous bursts of high-pitched laughter), but the cadence is there, the self-awareness is there, and random acts of physical comedy (utilizing his lanky form with precision) are also there. As the rest of the episode proves, everything we would come to know and love as Conan is all here — he just doesn't know it yet.

David Letterman made a name for himself by deconstructing the late-night formula. He would often have guests who were there simply because they were strange and the interviews would be awkward. He also did exaggerated bits that flew in the face of the traditional late-night trope of appearing dignified and classy. Conan would eventually take this baton and run with it to new extremes with hilarious and surreal characters and a classic bit where Conan interviews talking pictures of famous people like Arnold Schwarzenegger.

His first attempt at building on Letterman's legacy and making it into his own came after introducing his sidekick, Andy Richter, along with band leader Max Weinberg.  Conan and Andy then parody a tired late-night gag of finding "real" curiosities from small newspapers. Right out of the gate, they show an image of a road sign pointing to a pedestrian and reading "Adolf Hitler." This lets the audience know what kind of silliness they're in for from the jump.

As they continue to assure the audience that all of these snippets are real, the stories become more ludicrous. The funniest of which is about a woman who was hit by a bus and taken to the hospital. According to the story, her name was Louise Hitbyabus and she was rushed to the hospital, where Doctor Helplouise saw to her injuries. Louise's husband, John Hopeshesokay, stayed by her side. It's a touching story and a brilliant piece of writing expertly delivered by novice Conan.

Telling jokes is all well and good, but the real test of any late-night host is the celebrity interview. The job of the host is to make the guest feel welcome, help them promote something, and never let the audience get bored. As Conan gained more experience, he became one of the more adept interviewers on TV. He knew how to save an interview when the guest was bombing and how to go with the flow when they decided to get wild and crazy. In this first episode, though, he is visibly finding his way.

Luckily, his very first guest was John Goodman. They make a big show of celebrating the fact that he's the first guest with a gathering of paparazzi, and someone dressed as the mayor giving Goodman a metal. Again, this is all a way of making fun of the fact that no one is expecting this show to succeed by pretending like this is some seismic moment in television history when — at the time — it was anything but.

Conan holds his own during the interview. Since Mr. Goodman is promoting "The Flintstones," Conan can flex his knowledge of the original series and set up Andy to pick on himself a little bit. There's an unfortunate anecdote about doing press in Japan where Goodman does a culturally insensitive and stereotypical impression of a native Japanese speaker, but most of it goes off without a hitch. Plus, it ends with John Goodman's leg-wrestling George Wendt, who played Norm on "Cheers."

The show shines because of all the strange jokes that don't really seem to fit but are still funny. These are the moments where we really get a taste of the kind of comedy Conan O'Brien likes. They also further the notion that Conan is just as capable of turning late-night on its head as David Letterman.

After a commercial break during the interview with John Goodman, Conan is informed that they have to break for a special effects technician. This is the sort of thing shows will do before cutting to commercial or addressing a breaking news story. it makes you think that the special effects technician might have something important to say, but it's just a bearded guy in jeans and a flannel shirt doing an interpretive dance to the Phil Collins song "One More Night." It's quick and suggests that this individual has a whole inner life that we're only meant to glimpse as he shares his art with us.

Then there's a segment where sports commentator Bob Costas promotes the upcoming episode of his show "Later," set to follow "Late Night with Conan O'Brien." Under normal circumstances, Costas would likely talk about his guest and say something like, "Stick around after 'Late Night.'" Instead, we get to see a segment from the show where he interviews two surviving members of "The Wizard of Oz" cast and everything goes off the rails when Costas eats an apple from the branch of a talking tree.

Drew Barrymore is Conan's second guest, and he looks as though he couldn't be more nervous. She does her best to keep the energy up and remains engaged while Conan stumbles. They talk about her role as the eponymous Amy Fisher in the TV movie "The Amy Fisher Story" and the fact that she's living in a small Texas town while filming the western "Bad Girls" with Madeleine Stowe, Mary Stuart Masterson, and Andie MacDowell. Awkwardly, Conan doesn't have very many follow-up questions so the conversation sags a little.

The moment where the Conan we recognize today comes through is after a photo from Barrymore's Guess Jeans ad is shown. He immediately starts making lascivious noises and urging Andy to join in. This would become an ongoing bit with him over the years. O'Brien likes to point out the inherent silliness in things and one way he does this is to mock toxic male behavior by turning himself into a lecherous cartoon.

While some audience members may find this offensive (which is a valid reaction), Conan at least lets us know it's a joke right away. After he repeatedly howls, he apologizes to Drew and directs her to the cue cards where all the sounds he just made were, in fact, written down for him. "Everything's written down for me," Conan says. "The network is so scared," he continues, taking a moment to turn the joke on himself.

Conan and John Goodman worked together well. Drew Barrymore had to prop Conan up a bit. Before legendary comedic actor Tony Randall stepped out, on the other hand, he must have decided that he was going to be the one in control of the conversation.

The third interview on a late night could easily be the worst. Thanks to years of working in film, on stage, and on television, though, Tony Randall knows how to work an audience. After sitting down, with all the earnestness in the world, Randall says, "I just wanted to say before anything else that it's a real honor to be on your first show." Conan thanks him, and the audience applauds. Randall waits for the appreciation to die down before saying, "Not so great an honor as to be the first guest, but..."

Conan's inexperience is putty in Randall's hands. Conan has been making fun of himself the entire night, but Randall shows him how a master does it. He calls Conan's outfit a bar mitzvah suit, suggesting it isn't befitting a late-night host. Even when Conan tries to own the look by saying he's going to a friend's wedding after the show, Randall hits back with, "No, you should go to a friend's bar mitzvah after the show." Randall's gibes are all in fun and Conan takes them like a champ.

How do you end your first episode of television? One might think that Conan would most likely want to get out of there as quickly as possible to recuperate. Maybe he could just look at the camera, wave, and say, "That's for watching." Instead, though, he returns to the monologue stage and offers to serenade any insomniacs still watching the show. He does this by singing "Edelweiss" from the musical "The Sound of Music."

His rendition turns out to be so moving that both a nun and a nazi are weeping in the audience, while an emotionally touched John Goodman offers Drew Barrymore a shoulder to cry on. Tony Randall then steps out, Conan puts his arm around him, and the pair bring the number to a close. Of course, when Randall tries to sing on his own, Conan shuts it down instantly. After that, the credits roll, and Conan can finally take a second to breathe and relax — until the next night.

The big takeaway from this first episode is that all the puzzle pieces of what would become "Late Night with Conan O'Brien" and "Conan" on TBS are there. The issue for the individuals making the show is figuring out how to sand down the rough edges of the pieces to make them fit together and discarding everything else. Everyone involved was finding their way and hindsight tells us that they will get there and that "Late Night with Conan O'Brien" will be something truly special.