If you tuned in to NBC at 12:35 a.m. on September 13, 1993, you witnessed late-night history in the making. Jay Leno had inherited The Tonight Show from Johnny Carson in 1992, and a deeply pissed-off David Letterman had decamped to CBS. That meant a new host for Late Night had to be found. NBC turned to Lorne Michaels, who tapped 30-year-old Conan O’Brien. When NBC announced the identity of the man who would take over their decade-old franchise, TV critics, audiences, and even Letterman himself had the same question: Who? O’Brien, now regarded as one of the best hosts in the medium—one who spent nearly 30 years on the air—had minimal on-camera experience when he landed the job. As he once quipped to a journalist who’d called him a relative unknown, “Sir, I am a complete unknown.”

To be fair, O’Brien had already been one of the era’s sharpest comedy writers, working on Not Necessarily the News, Saturday Night Live, and The Simpsons, not to mention spending two years as the president of the Harvard Lampoon. Those who witnessed his high-energy pitches in writers rooms were already aware of how brilliant he was. Now everybody in every living room in America just had to agree.

NBC suggested that Letterman not be mentioned in the inaugural episode on September 13, but O’Brien knew that was absurd. He, his head writer Robert Smigel, and his team found the perfect way to address this head-on. The cold opening found O’Brien walking down the street cheerily, as everyone he encountered greeted him with a similar refrain: “You better be as good as Letterman.” Then O’Brien retreated to his dressing room and—while whistling—prepared a noose to hang himself before a crew member informed him that it was time to go on. That’s how Conan O’Brien introduced himself to the world.

The opening let audiences know what they were in for: silliness with splashes of intellectualism and edginess, plus a final coating of self-deprecation. It was a far cry from Letterman’s beautifully constructed sardonic style or Leno’s more traditional desk jockeying. It was a new show for a new generation.

To mark the show’s 30th anniversary, Vanity Fair spoke to O’Brien and many of those in his orbit about that wild first year.

LORNE MICHAELS (EXECUTIVE PRODUCER, LATE NIGHT WITH CONAN O’BRIEN): There was a group of us who wanted Letterman [to host The Tonight Show instead of Leno]. David decided to go to CBS. And I got a call from NBC president Bob Wright, who said that they were going to announce that I was producing the new Late Night show.

DAVID LETTERMAN (HOST, LATE NIGHT WITH DAVID LETTERMAN): I remember in that overlap transitional period, there was so much attention to the change. “Is he going to stay? Is he going to leave?” In the beginning, it was kind of exciting. And then I soon sickened of the attention because I was unaccustomed to it. It really began to be superficial. And I felt my ego had been set on fire and I can’t possibly stand it anymore.

MICHAELS: Everyone who had been in late night was a baby boomer. I think it was “Who do we know in the 28-to-35 group?” We looked at a bunch of people, and I talked to Conan about being the head writer on it.

ROBERT SMIGEL (HEAD WRITER, CONAN O’BRIEN): Conan joined Lorne in the pursuit of finding the right host. He went out to dinner with various people. The more he did, the more he thought, These guys are great, but I kind of think I could do it.

LISA KUDROW (CLOSE FRIEND OF O’BRIEN’S AND EARLY GUEST, CONAN O’BRIEN): Conan was spending time looking for who the host would be. He knew he wanted to do a show that was not just celebrity interviews, but [hosted by] someone who knew enough and who read enough to ask intelligent questions of scientists or authors or other people too. And I said, “So it sounds like you want you.” And he said, “That would never happen.”

O’Brien had been thinking about what he wanted to do next in his career. The logical next step was shifting from writing to performing. He told Michaels he was bowing out of the head writer role, and the network brass at the time continued to search for a host without him. Michaels, producer Jeff Ross, president of NBC’s West Coast division Don Ohlmeyer, president of NBC entertainment Warren Littlefield, and executive vice president of late-night and special programming Rick Ludwin headed for the Hollywood Improv one night in April to scout talent. They didn’t see anyone they were ecstatic about. The next day, they met in Ohlmeyer’s office.

JEFF ROSS (PRODUCER, CONAN O’BRIEN): Lorne brings up Conan’s name and says, “Well, Conan maybe could host it.” And the NBC guys were going, “You think?” I remember Lorne turned to me—not knowing that I had never met Conan—and goes, “You think?” And I go, “Maybe.” Then NBC said, “Can we test him?” Lorne turns to me and says, “Jeff, can we test him?” And I was like, “Sure…”

MICHAELS: The more that I spent time with him, the more I started to see it. I thought he had the intelligence. In a small room, he was truly funny, and fast. So I thought more and more that he could do that.

CONAN O’BRIEN (HOST): There isn’t another person in show business who could’ve said, “I have an idea. He’s a writer on The Simpsons but he’s got a good look. And I bet in time, he’d be a good host.” No other fucking person in show business could’ve said that.

SMIGEL: I was excited for him, but I was scared. I remember saying to him, “Man, that is a tough way to get on TV.” I wasn’t the best person to rev him up in that way. As much as I wanted him to make it, I just reacted honestly. But he said, “If I get this, I really want you to be the head writer.”

With short notice, O’Brien’s team managed to get Mimi Rogers and Jason Alexander as guests for his audition, and he won the crowd over when he told Rogers, “People always say that it’s tough to be a model. Turning a big crank is tough!” The joke helped get O’Brien support within NBC.

O’BRIEN: The audition was fun because I had nothing to lose. The minute I got out there and there was an audience and I got to sit behind the desk, I loved it. It felt very much like linguine meeting marinara sauce for the first time.

SMIGEL: After that, my confidence went completely in the other direction. Like, “He’s going to be enormous! I can’t believe how big our show’s going to be!”

O’BRIEN: You could say I had more confidence in that audition than I had in the actual show for the first year.

Even though O’Brien had impressed NBC, they were still thinking about going with Garry Shandling instead.

O’BRIEN: Lorne Michaels called me and said, “You’re not going to get it. It’s going to go to Garry Shandling. Shandling’s going to do 12:30.” I hung up and I remember saying to Lisa Kudrow what I just heard, and I said, “Yeah, I don’t see it. Garry’s a peer of Dave’s.” And at the time, he was doing The Larry Sanders Show. He’s getting all this critical praise for making this amazing show that satirizes the form. I don’t see him going in and doing Monday through Friday.

KUDROW: I don’t know how much we talked about it. I just knew, “You’re trying to replace David Letterman. No one replaces David Letterman. You’re no one.” [Laughs.] It can’t be anybody that an audience would know.

Sure enough, Shandling was out. The show went to the underdog.

O’BRIEN: It is a moment that is seared in my memory. It’s the day of a recording of a Simpsons episode. We’re all sitting around a table when someone in the room said, “Conan, there’s a phone call for you.” And I went up and got on the phone and it was my agent at the time, Gavin Polone. And in a quiet, calm voice he said, “You’ve got 12:30.”

ROSS: I went out to lunch and my assistant handed me all my messages, and it’s like Rick Ludwin, Lorne Michaels.… The names made me look at this and go, “Oh, my God. He got it.”

LETTERMAN: I didn’t know what he looked like, I didn’t know what he sounded like, I didn’t know anything about him. So my reaction to Conan behind that desk was similar to everyone’s reaction, which was, “Now who is this? Why is this guy here? Who will be the real host?”

Immediately after giving him the job, NBC had O’Brien rush to Burbank to appear on that night’s episode of The Tonight Show so Leno could introduce him to America. The next task became figuring out what on earth the show would actually be like.

O’BRIEN: We didn’t have much time. I get selected in April and I don’t really get to start working on the show until late May.

SMIGEL: We idolized Letterman, which affected a lot of my approach. I was desperate to do anything Letterman didn’t do.

O’BRIEN: First there was Carson. Then there comes, for our generation, Letterman, who is ironic. Then we thought, Okay, what comes after that? It needs to be more cartoony. The performances can’t be a wink and a nod. This has to be a new thing. This has to be postmodern. And I think what we ended up with was: It’s got to have elements of SCTV and Pee-wee’s Playhouse. We had all of these very strong—almost religious—beliefs about what this needed to be.

SMIGEL: I said, “Do we have to call it Late Night? Can it just be a brand-new show, so it doesn’t feel like we’re stepping into Letterman’s shoes?”

O’BRIEN: If it was Late Night With David Letterman and then we called it something else, maybe that would help lessen any comparisons between me and Dave.

SMIGEL: I suggested Nighty Night. Conan liked that a lot because it felt appropriately silly for his personality. And then, oddly enough, Lorne Michaels came to us and had the same notion that we should change the name of the show. His idea was calling it Night Night, which I thought was better than Nighty Night, because it wasn’t silly in an alienating way.

O’BRIEN: I remember us going and pitching this idea to Rick Ludwin. We say to him, “Okay, we don’t call it Late Night because we’ll be compared to Letterman. We call it Nighty Night—or Night Night—with Conan O’Brien.” And then he just cut us off and went, “Well, let me tell you something. Late Night has been a very lucrative franchise for us. It has existed for 11 and a half years under David Letterman. We have three franchises. The Tonight Show, which began in 1955 and has had multiple hosts. We could see that happening with this franchise, Late Night. And there is no way in God’s green earth that you are changing our franchise.”

In addition to Smigel, producer Jeff Ross became an integral part of the team.

O’BRIEN: Jeff Ross is just a perfect producer for me. He’s really good at making it happen. Jeff’s heart beats once every nine minutes. He works at that temperature that really helps work with me and offset my madness.

By early summer they started filling out the writers staff with what now looks like a who’s who of comedy: Smigel, Bob Odenkirk, Andy Richter, Dino Stamatopoulos, Louis C.K., Marsh McCall, Michael Gordon, Amir Gollan, and David Reynolds.

ANDY RICHTER (SIDEKICK AND WRITER, CONAN O’BRIEN): I got a call from Robert saying, “Would you like to meet with Conan and maybe see about getting a job as a writer on the show?” And I said, “Sure.”

O’BRIEN: Andy and I met at a diner. He sits down opposite me and I had ordered already and the waitress said, “What do you want?” And he said, “I’ll have a bowl of borscht.” It was really hot outside and he ordered a big bowl of beet soup.

RICHTER: We just hit it off. It’s a real joy when you meet a person who just wants to be silly and is into having fun. The people that I love the most in this business are people where that’s their first priority. Like, “Yeah, we’ll do a show, and it will be good and everything, but first and foremost, we gotta have fun.”

O’BRIEN: I called Robert and I said, “Let’s hire him.” Robert said, “Well, he hasn’t submitted a packet yet.” And I remember wanting to hire him without him even submitting a packet. As a writer!

DINO STAMATOPOULOS (WRITER, CONAN O’BRIEN): I submitted a bunch of comedy bits to Conan. I said, “I don’t really wanna work on this show, but I just want him to have those comedy bits without me being on the staff or anything like that.” And then they hired me anyway.

SMIGEL: Dino wrote the best packet that I’ve ever seen anyone write. He was a no-brainer, which says a lot because I love to agonize over every decision in my life. But Dino was the easiest hire we made.

STAMATOPOULOS: I remember seeing Louis C.K.’s packet and getting really excited by it. Louis came in for an interview, and I started congratulating him on getting the job way before he got the job. And he’s like, “Don’t do this. I’m just going to be disappointed.” I’m like, “No, you fucking got the job.”

BOB ODENKIRK (WRITER, CONAN O’BRIEN): I think Smigel trusted me to care about the show and maybe know Conan a little bit. More than a new writer would know him. I came to New York and I was here for three weeks in the early days. I saw some of the first test shows. Then I went back to LA and I would fax my ideas in.

O’BRIEN: I look at the snapshot of the very first writing staff, and now it looks ridiculous because we look like a barbershop quartet that would perform at Dwight Eisenhower’s inaugural. It’s super white and male. I think it’s important not just to let it rest with “Those were the times.” Yeah, those were the times, but times change because people make them change. And you just have to be honest and say at that moment, that wasn’t top of mind. It’s a missed opportunity, and that’s our loss. I was glad we were able to evolve. But do I wish we had led the way? Yeah, that would’ve been awesome.

Richter was lured into the sidekick role in fairly short order.

RICHTER: Robert said, “Hey, could you just go down and sit next to him [for a rehearsal]? Just keep him company?” Then as we got closer, he said, “Would you like to be the sidekick on the show?” I said, “Well, aren’t we gonna have, like, lots of different opportunities to be sketch players?” He said, “Yeah, yeah.” I was kind of hesitant. I said, “I don’t know. Maybe I just want to be one of the other performers and not be sort of nailed down to being myself.” And he said, “Okay. Well, think about it.” And he left my office, and the second he was gone, I was like, “Who am I kidding?”

O’BRIEN: It was so lifesaving to have this funny person who I loved sitting next to me. I needed someone to play off of, and Andy is one of the funniest guys I’ve ever met. We’re so different in certain ways. I run hot, he runs cool. I’m a hummingbird, and he’s sort of more stoic.

Another highly visible member of the team, drummer Max Weinberg, joined the show after running into O’Brien in Manhattan.

MAX WEINBERG (BANDLEADER, CONAN O’BRIEN): My wife and I are walking south on Seventh Avenue, and standing at the corner waiting for the light to turn, holding a paper bag in one hand, was Conan O’Brien.

O’BRIEN: I’m walking to a drugstore, and I bump into this guy who looks like he works for H&R Block with his wife. And it’s Max Weinberg.

WEINBERG: I said, “Hey, Conan. Max Weinberg from the E Street Band. Congratulations on the show.” We start talking on the corner. He doesn’t cross the street. So I said, “By the way, what are you doing for a band?” He looked at me and said, “Well, we’ve got some ideas.” And then he said to me—which is classic Conan—“Do you have any ideas?” I ask, “What are you looking for?” And he starts to describe, “We want something that’s very versatile. Kind of cartoony, a little Warner Bros. Something different.” And I said, “I’ve got just the idea.”

O’BRIEN: He said, “I could be your bandleader.” I thought, Is he insane? Does he think he’s going to get Bruce Springsteen and the E Street Band to be my band? [Laughs.] I said, “Really? You think Bruce would be down for that?” “No, no. Not Bruce. But I know these other guys.”

WEINBERG: Eventually I had three or four meetings with them. [Music booker] Jim Pitt calls me and goes, “We had a really great time meeting with you. We’d like to hear the band.” Here’s where it gets interesting. I never told them I had a band. All I did was tell them I had a great idea for a band. I hung up and I immediately got on the phone with every musician I knew.

O’BRIEN: Our band was crucial because they made us look and sound professional. I mean they showed up and blew the roof off 6A every day. Plus, they could start and stop on a dime.

When the show debuted in September, it didn’t take long for people to figure out that it wasn’t Late Night With David Letterman. The first show featured John Goodman, Drew Barrymore, and Tony Randall. In addition to the cold open, the show had leg wrestling and a Louis C.K. bit called Actual Items that parodied Leno’s Headlines with comically fake newspaper clippings. It closed with O’Brien and Randall singing “Edelweiss” as they cut to a nun and a Nazi crying in the audience. The reviews were not particularly kind—save for The New York Times—but the show benefited from the fact that The Chevy Chase Show had gone on the air a week earlier and became the fall season’s favorite punching bag.

STAMATOPOULOS: The first episode aired, and we all congratulated each other. Like, “Woo! We did it!” Then we went, “Wait a minute. We have to do one every day for the rest of our lives.”

SMIGEL: Reviews that pissed me off the most were not reviews that didn’t like the show but ones that said that we were ripping off Letterman. And it’s like, “You don’t understand comedy at all. That’s the last thing we’re doing.”

Late-night shows typically did comedy bits every evening, but more absurd humor drove O’Brien’s show, from fake guests to random comedy inserts in the middle of interviews to recurring bits like In the Year 2000. One of the most famous segments was done in the style of the 1970s animated series Clutch Cargo and found O’Brien pretending to interview politicians and celebrities while Smigel’s lips moved absurdly in a still photograph purporting to be a satellite link.

SMIGEL: I came up with In the Year 2000 [for a sketch show in Chicago with O’Brien and Odenkirk in 1988]. I thought, We’ll make predictions about the future, and the joke will be it’s nothing like how we picture the year 2000. Then I had forgotten about it, but when we were putting together this show years later, Conan said, “What about that In the Year 2000 bit? That could work. Me and Andy could do that.” And I wanted to have Conan interview celebrities and politicians as a performance piece. Then Dino just randomly in one meeting said, “We should figure out a way to do Clutch Cargo bits,” and I was like, “Let’s do it with photographs of celebrities and do that instead of having actors come in.”

O’BRIEN: I loved how brave those writers were. They were all so young. I think for almost all of them, it was their first TV gig. And so the beautiful thing about that Late Night show is nobody knew what the rules were. Nobody knew what was okay to try, so we tried everything.

ROSS: Lorne said to me, “You guys are going to try to do Saturday Night Live every night, and you can’t do it.”

SMIGEL: I had sort of a “Let’s fuck with the old talk show setup and just have things happen at any time during the show.” One of my ideas was that I wanted to have fake guests come on in between two other guests.

One week, O’Brien announced economist Woodrow Thomas on Monday night’s show. Thomas was bumped Monday, but O’Brien promised that he’d be back very soon. He was then bumped Tuesday, Wednesday, and Thursday. When he finally appeared on Friday, he went off on O’Brien and became unhinged. Only thing is, there was no such person as Woodrow Thomas. He was an actor.

O’BRIEN: In order to appreciate that joke, you’d need to watch all five nights. You have to be watching at 1:35 when we wrap up the show. This was a conceptual sketch that was meant for two people in America. And we didn’t care. [Laughs.]

SMIGEL: I can only remember one thing that Lorne said, “You’re not doing that again!” We did a character called Funny, Funny Joe. It was like a tribute to vaudeville. He would just keep singing, “I’m gonna make you laugh!” and then just do more and more degrading shit to himself, like take a bunch of eggs and crack them in his crotch.

O’BRIEN: I have sense memories, probably like PTSD. Like, I remember being in a hot tub with David Faustino from Married…With Children. Now, why was I in a hot tub with David Faustino from Married…With Children? [Laughs.] I’m just thinking about anyone tuning in to any of this and being justifiably confused about what’s happening.

JIM PITT (MUSIC BOOKER, CONAN O’BRIEN): William F. Buckley was in the middle of an interview, and Dino came out doing a bit called Skull Juice, where he was a vendor at a stadium and a sign said, “Skull Juice: 10 Cents.” Conan said, “Oh, Skull Juice. I’ll have one.” And the whole bit is that he squeezes his head and contorts his face and white juice comes out of his mouth.

O’BRIEN: We did a whole episode that was a takeoff on sitcom “bottle” episodes, where two cast members get locked in a meat locker or in a safe and that’s what the episode is. So we did an episode where Andy and I wander into a meat locker and it locks behind us. And we start having flashbacks. And then Jamie Farr came in and he had a flashback, but it was just to an episode of M*A*S*H that we played—I’m quite certain—illegally. [Laughs.]

WEINBERG: It was all about experimentation. What works? What gets a laugh? It was wild. Unless it’s embarrassing to my family, I would do anything. They used to say, “Have Max do it. He’ll do anything.” I was always the punch line. Conan said to me, “Your stuff’s funny because you are a straight guy. You don’t buy into the foolishness that we do. That’s the character.”

SMIGEL: Another rule I had was that Conan could not do remotes as himself. I just didn’t want to put Conan in that position of looking like he was trying to do anything Dave did. So I would just send Andy out. Somehow, I thought that there was no pressure on Andy to do it.

Richter went to a Grammys party and asked everyone when Thin Lizzy was going to get a tribute. He went to the Super Bowl and clearly knew nothing about the game. Most memorably, he went to Woodstock ’94, where he wound up sliding in mud with attendees.

RICHTER: Robert was with me on that one. We collaborated a lot. I was kind of crabby all day. It was hot. And we started seeing people in the mud, and then we got to the point where people were going down the hill. I just turned to Robert and said, “I gotta go down that hill, don’t I?” And he said, “Yeah, you gotta go down there.” The minute I saw it, I knew, Yeah, we need that shot. And so I did, and it was fun. But I did get poison ivy.

PAULA DAVIS (TALENT BOOKER, CONAN O’BRIEN): Conan was unproven, so we didn’t have the relationships that we do today with publicists and studios. So we called on our friends. We had a lot of SNL people, a lot of NBC people.

JANEANE GAROFALO (GUEST, CONAN O’BRIEN): I remember there were times where it was like, “So-and-so isn’t coming. Can you just come on the show?” “Yeah, of course.” I would either be blocks away or upstairs [at Saturday Night Live].

SARAH SILVERMAN (GUEST, CONAN O’BRIEN): Conan was really my first big break. I got hired and fired from Saturday Night Live in his first year, but he continued to have me on as a comic on the couch, which gave me an incredible opportunity to try new jokes and weird stuff in a different format than standing behind a mic.

GAROFALO: They would sometimes let Ben Stiller and I do fun things. That’s what was really fun about it. Not just being on the panel, but instead doing a character or a skit or something like that.

DAVIS: I would look at tapes of comedians and pull what I thought was worthy. And I remember seeing Marc Maron and we booked him early on.

PITT: From a music standpoint, I knew going in that we weren’t going to get the big names. So why not lean into doing stuff that’s different? It also coincided with the boom in alternative music. We gave debuts to a lot of artists. A band like the Cranberries, it was their first US television appearance. We premiered Green Day and Jewel. There are bands we relied on a lot. They Might Be Giants were a phone call away. They were over in Brooklyn. They definitely got some last-minute calls.

ROSS: All I was doing was trying to sort of keep the network at bay and just try stuff until we figured it out. We kept learning as we went.

O’BRIEN: Things got really rough for us in November, December, January, February. We were exhausted. Reviews were bad. Ratings were not great. I think the network was scared or unhappy or angry or all three. That was a very hard period. And I remember the thing that saved me is that we had a show to do every day.

RICHTER: They gave us ratings hurdles, and we met them. There was never any “Well, good job! You did it! We set a bar for you, and you cleared it. Nice work, fellas.” It was like, “All right, you did that. Well, the show’s still too expensive. Let’s fire the band.”

SMIGEL: The network didn’t like Andy at all after the first show. I remember one executive told us, “I want you to shoot him. He’s terrible and he’s just bringing Conan down.”

RICHTER: It was all so absurd. Critics could say, “Late Night With Conan O’Brien is a boring, juvenile shit show. And that fat slob Andy Richter is a no-talent jerk,” and it would still be like, “Hey, I’m in the paper!” [Laughs.] I never knew there were so many ways to call someone fat. It was “portly,” “cherubic.” You go through the thesaurus for “fat,” and I will have been called it.

O’BRIEN: We were very naive. I just had to go through the spanking machine. I had to develop from a fetal pig to a full-size pig in front of America. And that just had to happen. There was no way around it.

JEFF GARLIN (GUEST, CONAN O’BRIEN): It took him a while to learn how to be a broadcaster. Even if the person you’re interviewing is boring as shit, which is usually what an actor is, you’ve got to listen as if you find it really interesting. And he got really good at that.

ODENKIRK: He got a lot of negative reviews, and that is crazy to me. I mean, the guy’s trying to figure it out. He’s coming in with the greatest spirit you could ever ask for.

KUDROW: He just kept showing up as him. He just kept being himself, with his own kind of humor and comedy, where if you just keep doing it, then people get it: “Oh, that’s you. This isn’t an awkward thing. It’s you.”

MICHAELS: They were going to beat him up. He was going to take a lot of punches before the time when they would acknowledge that he was doing okay. Because there was no avoiding it.

O’BRIEN: As dark as things got, the fact that—if they were going to screw with me—they were going to have to go through Lorne probably helped us somewhat.

The network remained antsy. One Friday night, Ross got a call saying the show was in imminent danger of being canceled. Rumor had it that Greg Kinnear would replace O’Brien. Ultimately, the show got renewed on a precarious 13-week basis. Its saving grace was Ludwin, who had kept Seinfeld on the air when nobody else at NBC understood it.

ROSS: We were on the hairy edge of cancellation a bunch of times. But Rick Ludwin was the guy who kept going, “No, no. He’s got it. They’re onto something, these guys. Leave him alone.”

O’BRIEN: When push came to shove at some crucial moments, Rick made the difference.

The show got an unexpected gift from O’Brien’s legendary predecessor as well.

O’BRIEN: At a real low moment, I think I had maybe sent Dave a note saying he was welcome to come on the show at any time—not thinking that he would. His show was kicking ass and he was kind of the new king of late night.

ROSS: [Letterman’s producer] Robert Morton calls and says, “Dave wants to go on.”

O’BRIEN: I was excited but also terrified. “What’s he going to say? What’s going to happen?” It felt like a do-or-die moment.

LETTERMAN: I was excited. It was kind of like, “Dave, it’d be great when you’re done with varsity practice if you could swing by and talk to the freshmen.” It was kind of like that. I’m nothing if not self-centered. So I felt like, “This would be great for me.”

ROSS: I think we had to go to Leno just to say, “Hey, we’re doing this” and whatever. And Jay was like, “Yeah, sure, that’s fine. That doesn’t bother me.” The network was not thrilled about it.

O’BRIEN: Dave came on the show and couldn’t have been more gracious. He complimented the show. He said he was really struck by how much we were doing. We were trying so many different strange things and working so hard. But you didn’t read anything complimentary. You didn’t get any encouragement from the network. It just felt like, “Does anyone notice?”

LETTERMAN: I remember I was quite taken by the quantity and the quality and the kind of comedy they were doing, which was not similar to anything I had done. I was legitimately impressed by that.

SMIGEL: It was just an incredibly generous thing to say. And the fact that he said it on the show—I can’t express how significant that was at that time.

LETTERMAN: I remember I said to Conan, “How exactly did you get this job? Was it a theme writing contest?” Big laugh. And I’m Mr. Big Shot.

O’BRIEN: And I said, “Yes. It was a ‘What would you do with a talk show’ contest, and I came in fourth.”

LETTERMAN: Bigger laugh. And I thought to myself, Ooh, this kid’s pretty quick. So that to me was greatly telling and something I truly admired.

O’BRIEN: And he had a real genuine laugh, and the audience laughed. And that kind of encapsulated my sense of humor in one exchange.

ROSS: That was a huge turning point. It helped our confidence and Conan’s confidence. Dave was hilarious. He was really generous about it and cool.

O’BRIEN: It allowed us to almost relaunch. People came and checked back in on the show. I would be lying if I said it was this miraculous moment where our ratings went through the roof and we never had problems again. We still had at least another year or so of real struggle.

ROSS: Even though it’s probably bullshit, it felt like “Well, they can’t touch us now.” They probably did try to cancel us after that, but that’s kind of how it made us feel.

Over time, a loyal following emerged. College kids, in particular, latched onto the show. It wasn’t until the summer of ’94, however, that the staff had any sort of awareness of this.

STAMATOPOULOS: The first few months, there was nothing. It was like, “Who is this guy? Why did the audience wrangler pull us into this place when we were having fun eating Sbarro pizzas downstairs?”

O’BRIEN: Then we hit the summer and suddenly the audiences became great. I didn’t know what was happening. And then it dawned on me. Colleges let out. So college students started to come.

ROSS: People showed up knowing bits. It made us feel like we were onto something. I don’t think the network noticed it, but we noticed it.

ODENKIRK: What I was struck by was that months in, Conan was even more excited, charged up, driven to win the audience over than he was when we first started. I saw him doing it, and I thought, Oh, my God. They really picked the right guy.

O’BRIEN: NBC sent a guy to ride herd on us, and he was really rough on us. He’s telling us, “This is all wrong. Don Ohlmeyer sent me here to kick your ass.” And then after he was done reading us the riot act, he went to visit his son at Boston College. He was hanging out in the dorm room and he said, “So what do you kids like to watch?” And all of them said, “Oh, we watch Late Night With Conan O’Brien. We really like that show!” And he had just told us pretty much that we were shit. [Laughs.]

ROSS: [In 1999] we did the show in LA. At this point, we had turned the corner. And this executive called us to his office. He really didn’t like us in the beginning. Conan and I were like, “Ugh. I can’t believe we’re still having to deal with this.” And he sat us down and he said, “Guys, I have to apologize. I was wrong.”

RICHTER: It was all pretty magical. That I got to work in that building on a nightly comedy show for seven years is really the pinnacle of some version of what I set out to do.

SMIGEL: It was the most exciting job I’ve ever had. It’s so fun to remember.

O’BRIEN: The story of how I end up as the host of that show and then what we do with it is highly improbable. You can draw it, you can diagram it, it just seems kind of crazy.