Democracy Dies in Darkness
End of a late-
night era: 28
memorable Conan moments
Writers, staff and celebrity guests
share their favorite stories from
O’Brien’s nearly three decades on air
(Brinson+Banks For The Washington Post)
June 23, 2021
In September 1993, as Conan O’Brien sat down at the desk of NBC’s “Late Night” as David Letterman’s replacement, America had one question: Um, who is this guy?
That spectacularly coifed host would go on to become a TV legend — and on Thursday, he will conclude his nearly three-decade run in late-night TV with the final episode of TBS’s “Conan.” It has been 28 years of delightful weirdness, bizarre characters, trips to meet his Finnish doppelganger, a “Walker, Texas Ranger” lever
, a nationwide tour after his brief and dramatic stint
on “The Tonight Show,” and so much more.
O’Brien, 58, will continue his popular podcast
, and he already has a weekly show
lined up for HBO Max. But as this marks the end of an iconic TV chapter, we asked some of O’Brien’s writers, staffers and funniest celebrity guests for their favorite memory from being on (or watching) his late-night shows over the years. Quite a few responded, and here’s what they had to say.
(Some of these stories have been lightly edited and condensed.)
‘Late Night,’ ‘Tonight Show’ and current ‘Conan’ head writer
I am not related to Conan, just happen to have the same last name. But, Conan likes to tell naive interns that I’m his cousin and he had to hire me because he owed our Uncle Frank a favor. He tells them I’ve never worked in comedy before and I used to sell lawn mowers door to door. They believe him.
I always loved being on Conan’s show and will miss doing it. The show was excellent fun and always amusing. My favorite skit was when Conan and I rode my Friesian horses
, with Conan wearing a wig. Maybe now he has time to grow his hair as long as the wig he wore!
The first time I did Conan’s show, I want to say it was for “Clueless.” It was the first thing I’d ever really done on television and he had only been on for a little while. I remember feeling self-conscious on the show, thinking, “Nobody knows who I am. Why would anybody care what I have to say about anything?” It’s a bit of a hazy memory, but I remember telling some story and halfway through just bailing on it, just stopping. And I remember Conan laughing at the fact that I just gave up. I felt as if nothing was said between us, but there was an appreciation for just the absurd dance that we were both doing, as these guys talking about something that wasn’t particularly interesting. There was something about his laughing at me bailing on it that made me feel comfortable.
I feel like with Conan, his sensibility and what really makes him laugh
is the kind of stuff that would not really fly on television. In a way, there’s almost an anti-comedy feel for it: This is going to alienate people, but it’s going to make a small number of people really
laugh. So to be able to retain that and then marry that sensibility with doing a consistently funny show and one that is accessible — the great ones can pull it off.
Former president of Finland and Conan’s ‘international twin’ from one of his earliest remote segments
We laugh very much about those shows
. They were really a surprise for me. I didn’t know that they would do that. So it was a big laugh. I think that Conan’s sense of humor — it’s a little like [self-deprecating] British understatement, so we like it.
[My hair] is not that red — I mean, always in the TV and films, somehow they [try] to make me like Woody Woodpecker. The people who see me outside, they say, “Oh, you are not at all so red-haired.” But no, it’s because of the light, the spotlight … so when I met Conan, I was laughing, and said that, “Somebody would say that you are my son or my grandson.” Then I asked [do I look like] your mother’s side or your father’s side?” So he said, “Oh, my mother’s side.” So that was very sweet.
President Clinton [once] asked me, “So, could you tell me, how did you feel when [Finland was voted] the best place to live? I told him, “You know that the first man in the street they would ask this question … that man would say, “Is the world such a miserable place that we are best?” Now you see why Conan is popular in Finland. His [humor] is exactly the same.
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‘Late Night’ writer and Triumph the Insult Comic Dog
Conan and I were good soldiers at “Saturday Night Live,” sneaking in some weird scenes where we could but always trying to serve the show’s needs with accessible but hopefully smart ideas. When Conan got “Late Night” we would finally have a playground for all our pent-up idiocy. We did topical interviews with celebrities by “Clutch Cargo”-ing them
(using their publicity photos but having an actor’s mouth provide the voice). The first interview was with President Clinton, whom I played as a carefree hillbilly, gleeful that he could say anything he wanted at 12:30 a.m. when no one was watching. In rehearsal I asked Conan to “feed” Clinton by holding up his mug to the photo while I loudly slurped his water. Pretty funny, but then Conan suggested I lap up the water with my tongue like a kitten.
The Clinton bit was on our second show … our premiere had gone very well but this bit was our first clear home run, and lapping up the water was our first big applause break in a sketch. That little slice of stupidity will always be my sweetest memory in show business, because it was two close friends breaking through in one moment and doing it together.
Actor and ‘Late Night’ writer
At SNL, when I met him, Conan was a whirling, hand-wringing, spitfire of comic riffs and nonsense. I figured normal people would be overwhelmed by this O’Brien fella if they ever saw him in his normal, everyday, unhinged persona. Cut to a few years later … we were shooting hoops at Fairfax High School on a gnawingly hot L.A. day, Conan was a few days away from seeing a lineup of possible hosts for “Late Night.” Conan swears he wasn’t thinking he could host. But he asked me, “Would you want to host?” Now, this was not a realistic thing, so I think he was asking, “What do you think of the challenge of that job?” And for me, the answer was “No” because I don’t like talking to celebrities much.
A week and a half later, after what sounds like an “okay” but uninspired evening of auditions, Conan did his impromptu test run of hosting. Gotta give it to Lorne [Michaels, SNL creator] for taking this crazy wild swing and supporting someone genuinely fresh. Conan impressed me with his indefatigable energy and commitment, despite all the negativity of the reviews and the general uncertainty of the audience that greeted the show those first few months. All these years later he still has that energy, he loves the audience, and he’s loony as a loony-bird, and it all worked out great
. Lucky us!
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Comedian and actor
We have such a history together — during our interviews, we very seldom get to the actual questions that are prepared because we’re kind of digging at each other and teasing each other about certain things. He would always stop in the dressing room beforehand and say hi, and say hi to my son and my wife. Then after the show, he would always invite me into the staff meeting to talk about how the show went. I would constantly keep steering the conversation toward my segment and how great that was.
When he first got “Late Night,” I was at 30 Rockefeller Plaza, and I would come down from the 17th floor where we did SNL. And I would sit on the floor right in front of his desk, of course off-camera, and watch him do his show, which was a thrill. It was just fun to watch him evolve and find his footing and his style and take off.
(Dana Edelson/NBC/Getty Images)
‘Today’ weather anchor and co-host
The interesting thing about my relationship with Conan is that — I believe this is true — I actually hold the record for most appearances on Conan O’Brien. And it wasn’t because I was a vivacious and humorous guest, or that I was just witty beyond belief — it was because I was there. At the time, I was not only doing the “Today” show, but I was also doing local news at WNBC, which was literally right across the hall. So, whenever they had a guest drop out because of scheduling or weather delays or anything like that, I would get called. They would be like, “Oh, please, can you come?” So, I was always on the show
Comedian and actor
“Conan” was the first major talk show that had me on as an official guest on the couch, a couple of weeks after “Billy on the Street”
premiered. The day after I did his show, the producers asked me if I wanted to go to the Super Bowl and film a “Billy on the Street”-style segment there. … I was literally going up to the players right after they had just won the Super Bowl and confetti falling everywhere … and I’m asking them if they saw the Madonna halftime show. To this day, that is one of my absolute favorites.
Another thing I’ve always loved about Conan is he’s always really embraced and encouraged and supported new comedic voices. Unique voices, outside-the-box voices, and I’m definitely one of those. We did a segment his team brought to me where I was going to help him join Grindr
— people still talk to me about that. That was a few years before this super-inclusive LGBTQ stuff started popping up, especially in the comedy world, which has always been so straight and male-dominated. … And Conan just fully leaned into [the segment]. He wasn’t making fun of it, he wasn’t acting grossed out by it. He was fully embracing it. And we just had so much fun.
Comedian and actress
Everyone knows that Conan is the king of the late-night field piece and one of the most famous ones among Conan fans is from 2004 when he goes to play old-timey baseball
with a bunch of cute dorks who love dressing up and acting like they’re playing in the 1800s. At one point while in the outfield, Conan points to a plane in the sky and yells, “Ho! What is that demonry?!”
Comedian and ‘Tonight Show’ and ‘Conan’ writer
There was a moment when Conan found out that we were leaving NBC [and “The Tonight Show”], and Conan was kind of distraught about it. I can’t really remember when it was, but I think people were protesting outside of NBC. And all these people came and showed up to show him love. And everybody was happy, and he came outside to say hi to everybody.
I was with him, and other people were with him. We were all just outside to say hey to the people — they were holding posters and chanting, and Conan decided to just go and run down the street. And we were all running down the street in the rain, and all these people were running behind us, and they were just chanting, “Conan! Conan!” That’s when I was like “What the … is going on?” That was the moment I knew something magical was happening.
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As teenagers on mushrooms in Midtown, my friend and I accidentally walked into the audience of one of Conan’s first shows. Ever since, I had a great level of comfort with him as a host, as I still see him as an 8-foot-tall orange string bean with an Elvis hairdo. There is nobody I am more at home with talking about my goal of becoming a cyborg. He truly understood my interests and has a heavy catalogue of old pictures to reference so we easily sparred when discussing them. Conan is a legitimately weird and kind person who actually listens and responds, so I was able to forget about my stage fright and get lost in our conversations.
Actor and ‘Late Night’ regular
I remember that I was doing a sketch at Conan’s “Late Night” during the blackout of August 2003. The scheduled guest was either Melanie Griffith or Halle Berry (or both), but the show was canceled, of course. I do remember that they tried to do a show with generator lamps and flashlights. They actually had me sit on the couch and be the guest (which was truly the highlight of my career at that point!), but I don’t think that episode ever saw the light of day. In any sense of the term.
Conan and I have this very middle-school bit where he pretends to attack me mercilessly, and I stand there, both incredulous and indignant. Casual observers will look on aghast, but he and I know that we’re just playing with each other. (And I truly cannot express to you how delightful it is
Comedian and ‘Conan’ writer
After my interview [for a writing job], I left the studio, picked up my 3-year-old son from day care and drove back to my apartment. Maybe an hour or so later, I got a call from Conan and the head writer Mike Sweeney. They offered me the job. Through tears, I said “yes.” This was quickly becoming the greatest day of my life, and then … my kid starts crying, loudly, in the background.
They pounced. One said, “Wait, you didn’t tell us you had a child,” and the other said, “THE OFFER IS RESCINDED! NO KIDS!” This went on for about two minutes. I realize that, in print, this looks like an EEOC hiring violation, but believe me, I was laughing — the greatest day was being made even greater. Also, my son is now 14.
‘Late Night,’ ‘Tonight Show’ and ‘Conan’ graphic designer
One time, the producers wanted to come to my place back in New York to shoot my collectibles, and we got into a whole discussion about that, that I didn’t really want to have people coming into my place … That evolved into a couple days later, being called to do an interview with Conan one-on-one. I had no idea what it was about.
It turned out the segment was like a CBS “60 Minutes” interview where he’s asking me questions and then it turns out that he’s portraying me as a serial killer [who doesn’t want to let anyone into his home]. Once the questions were coming at me, I realized where he was going. I had done enough material on air to realize, “Well, they can edit this.” So I’m trying to be careful with what I’m saying — but in doing so, I’m saying stuff that’s even worse than if I just simply answered the question. So Conan was trying to keep a straight face as he was continuing, but it made for one funny segment
‘Late Night’ writer
I guess my favorite memory was Conan taking me apartment-hunting
, which ended up involving role-play with our patient broker Claudine and then showering on national TV to test the water pressure which, little did I know, would soon become viewable for the rest of my life. Oh, well!
Going on tour with Conan was an incredible experience and such a testament to his generosity when it comes to younger comics. He is so funny on and offstage in addition to being super humble and kind. It’s sort of unfair, really, how great a guy he is.
‘Late Night,’ ‘Tonight Show’ and ‘Conan’ writer
One memory I’ll always be very grateful for is Amy Poehler playing “Andy’s Little Sister, Stacy”
for the first time back in 1997. It was the first sketch I ever wrote at “Late Night,” and Amy took my very simple idea about a 13-year old girl with pigtails and braces having an unrequited crush on Conan and knocked it totally out of the park with her hilarious performance, running the gamut from adorable bashfulness to volcanic, homicidal rage. I’d known Amy back in our Chicago improv days and I’ve always been in awe of her incredible talent, but seeing her, Conan and Andy [Richter] have so much fun in that sketch is an especially wonderful memory for me and I’ll never forget it.
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(Paul Drinkwater/NBC/Getty Images)
Drummer and ‘Late Night’ and ‘Tonight Show’ bandleader
The late, great Rodney Dangerfield made an appearance, fairly early in my 16-year run. I learned a valuable lesson: The bandleader must always know the last joke of a comic. Towards the end of his stand-up segment, as I was off-camera perusing the next script segment, I suddenly heard a voice directed at me: “That’s your cue.” I looked up at Rodney standing about seven feet away from me and said “What?” “Play, play” he said, fairly vigorously. He wanted what we call a “chase” — play him across the floor over to the desk and when the guest’s posterior hits the couch — you button it up. So I hit it.
Legend that he was, Rodney Dangerfield did not miss a beat. He turned to Conan and then the audience and works my “mistake” into his act: “I tell ya — it’s the story of my life — even from a drummer — I GET NO RESPECT!” The audience — and I — roared.
Singer and actress
Besides the moments of my own where I’ve been lucky enough to be on his show
and stand exactly the height of his waist, there was a very funny moment that I witnessed that he had with Norm Macdonald. Norm proceeded to tell a joke, and let’s just say the joke went on and on and on and on and on. He finally landed the plane, and this is from one of the funniest men ever, Norm Macdonald. And at the end, Conan goes, “Is that it?” And it got a huge laugh, and he said, “Was it worth it?” I don’t know any comedian alive who hasn’t had the Norm moment, the Conan moment, and the audience moment. And that’s the magic of Conan.
Conan and Andy, they have this old-school thing — if you watch the old Johnny Carson shows, he never stepped on his guests. He knew that if the guest was killing, then the show was killing. That’s what I remember the most. If I was on a roll, I never, ever remember getting interrupted by them. And I remember countless times, Conan and Andy saving me if it started to dip.
Another big thrill is fans would get at me on social media and saying, “You really made Conan laugh
” or “I’ve never seen Conan laugh like that.” That took me back to how I never saw Letterman laugh like when I saw his Chris Farley interview. You just fantasize: “Can you imagine if I ever made someone like that laugh that hard? How great that would feel?” Because comedians, that’s literally how we connect with people, we make people laugh.
Comedian and actor
My favorite Conan memory is my first appearance
and hearing him genuinely laugh after a joke I made. It was at that moment I felt that I was on the right career path. Knowing I could make my hero laugh. My favorite personal moment was flying with him on his tour and seeing him interact with fans. He always made it a point to be curious and happy to meet a stranger and I will never forget that.
‘Late Night’ writer and actor
I got to meet David Bowie when he filmed
one of the “Celebrity Secrets” segments we used to do. He couldn’t have been nicer … that was genuinely thrilling getting to meet him and chat a little bit about music. Side note: I did the whisper voice for “Secrets”
and ended up making a little money from recording and residuals just from that one-word voice-over. Nothing crazy, but probably a few grand, which I guess is crazy for just whispering the word “secrets.” I bought a titanium road bicycle as a gift to myself, and the show’s casting director/fellow cycling pal Cecelia Pleva nicknamed the bike “Secrets.”
Andrés du Bouchet
‘Late Night,' ‘Tonight Show’ and ‘Conan’ writer
Our guest on one episode was the legendary Carl Reiner, and during his interview he brought up how much he enjoyed a sketch I had written and starred in a week or so earlier! The sketch was called “Nut Spoon”
and basically consisted of me as a cameraman doing a lot of yelling. I’m a fan of the bit, but in my opinion I’ve written plenty of funnier things on the show. But Carl Reiner was complimenting this bit, and it rocketed me out of my office and had me running up and down our third-floor hallway hooting and hollering.
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I mean, Conan is just brilliant. That’s a given. I feel he always pushed for the most innovative, original comedic sketches. The last one we did together was a physical race, which we spent all day shooting and unfortunately ended with him slipping and really hurting himself
. It was devastating to me to be any part of him hurting himself. I’ve just always been his biggest fan. I wish him continued success because I know there’s going to be the next great thing for him.
‘Late Night,’ ‘Tonight Show’ and ‘Conan’ head writer 2000-2015, current ‘Conan’ writer/producer
We were in Japan, all set to visit Hokuei, a city nicknamed “Conan Town”
in honor of a popular manga character, Detective Conan. The entire town had mobilized to roll out the red carpet for this flesh-and-blood Conan from the United States — we would participate in a ceremonial meeting with the mayor at city hall and attend a large barbecue in the town square, after first being welcomed by a crowd and news camera crews at the local airport. When we deplaned to zero fanfare, our local producer quietly informed us that we had flown to the wrong city. But thanks to the prowess of Japanese mass transit (via bus!), we made it to Hokuei in time for the mayor and lunch and shot a segment that is now one of my favorites, principally due to the fact it even exists.
‘Late Night’, ‘Tonight Show’ and ‘Conan’ writer
There are far too many moments to choose, both on-camera and off, that it feels like a disservice to pick one. So, for me, I am choosing the late-’90s! All of the late-’90s. Every show in the late-’90s. This was the run of years where I feel the show was a magical, frothing, bottomless trove of inspired, experimental, collaborative insanity. The shorthand that exists in creating fun pieces was already deep in our DNA, and I couldn’t believe how lucky we all were that Conan had brought us into his world and allowed us to have as much fun as is possible in a still unpopular time slot. I’m forever grateful to have been given the opportunity, and I don’t think we embarrassed the boss too much.
‘Late Night’ announcer
So you’re doing a comedy sketch in front of a live network television audience, and something goes wrong, technically or whatever, and the whole thing is just circling down the porcelain convenience. Not surprisingly, this happened several times through our 16½ years. Every time, Conan’s saves bested even what had originally been written. I buttonholed him at the west elevators one night, after one of those, and said, “I know it must shorten your life, but you are at your 110 percent best when everything goes [down the toilet], and you have to save it.” He said, “It does shorten my life, but thank you.”
‘Tonight Show’ and ‘Conan’ segment producer and comedy booker
I was the new guy hired at the start of “The Tonight Show” to primarily book the stand-up comedians. After a fantastic performance by Deon Cole, I received an email from someone on staff named “Chopper” raving about Deon’s performance and saying that we should hire him as a writer … I told my assistant that I had just received an email from someone on staff named “Chopper” who thought they could make big decisions about the show and he said, “Oh, that’s Conan’s email address.”
‘Late Night,’ ‘Tonight Show’ and ‘Conan’ associate producer
The past 26 years have been an ongoing adventure with far too many extraordinary moments to effectively mention: Riding a bicycle through the American Museum of Natural History at midnight, sneaking a rubber dog puppet into Madison Square Garden, stopping New York City traffic on Third Avenue to crack a 10-foot bullwhip, witnessing so many legendary musical artists of the 1990s make their early television appearances in our small studio, looking out over Radio City Music Hall from a ninth-floor window in 30 Rockefeller Plaza … I treasure all of it and remain forever grateful to these shows and our incomparable host.
Emily Yahr is an entertainment reporter for The Washington Post. She joined The Post in 2008 and has previously written for the Boston Globe, USA Today, the Lexington (Ky.) Herald-Leader and the American Journalism Review.
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