An Oral History of Conan O’Brien’s Favorite-Ever ‘Late Night’ Segment
Conan O’Brien ended his 16-year run as host of Late Night in February 2009 with a remarkable send-off: one final wild and memorable week of shows for his most dedicated fans. It included several “best of” reels as well as tributes to everyone from the Masturbating Bear to announcer Joel Godard. Then, on the very last show, Conan ran his “personal favorite” clip from his time on Late Night, saying, “When I leave this Earth, at the funeral, just show this because this pretty much says (what) I’m all about.”
In the remote segment from 2004, Conan ventures out to Old Bethpage Village Restoration, a museum on Long Island that sponsors an old-fashioned, 1860s era baseball game in which players use period-appropriate uniforms and sports equipment and play by mid-19th century rules.
For the first half of the seven-and-a-half minute segment, Conan wears his modern attire and genially pokes fun at the players and observers who never break character. Especially notable is one female observer (Nell Del Giudice) who is portraying the timid wife to a soldier in the Civil War. Conan, at his ad-libbing best, proceeds to relentlessly hit on Nell, telling her that her husband is a coward and likely dead and that, naturally, Conan should replace him as her suitor.
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The sketch then hits the next level of hilarity when Conan adorns himself in a period-appropriate baseball uniform and plays old-timey baseball himself, humorously berating his teammates as he pitches.
When watching the clip, it's easy for those familiar with Conan to see why it's his favorite. It’s a tightly edited segment that highlights one of Conan’s deep-rooted interests: history. While Conan deserves much of the credit for improvising his way through it, the sketch was crafted and overseen by writers Kevin Dorff and Michael Gordon, who join us here to tell the story of how it came to be.
The Pre-Game
Kevin Dorff: Back in the Late Night days, when we would do remotes like the Old Timey Baseball one, they would usually come in a very organic way. There were remote ideas that turned over in our minds for years, but they would never bear fruit. Then there were remotes that would show up and grow like kudzu, instantly. This one happened to be one of those.
Prior to this, I know that, for a long time, there had been a theory that Civil War reenactments might be a juicy place for Conan to go because he knows a lot about American history. But there are certain things about Civil War reenactments that are hard to get over.
The baseball idea came up because our stage manager, Steve Hollander, saw an article in his local paper, and he came to me and said, “This is neat. There’s this place that does baseball games with 1864 rules. Who knows, maybe you can even do a remote off it?” I said, “I don’t know, Steve.” Then I took it out of his hands and ran it up to Mike Sweeney, the head writer’s office. It was the quickest approval ever. We were setting it up less than a few hours later.
Michael Gordon: After it was all approved, Kevin very generously came to me, knowing I was a baseball fan, and said, “Do you want to help me out on this?” — as if he needed help — and I said, “Uh, yeah!” I couldn’t imagine any better assignment than this.
Leading up to the day of shooting, Kevin and I came up with a whole bunch of beats and stuff that we knew Conan wouldn’t use, but you have to do your job and you have to have stuff ready just in case.
We knew he wouldn’t use it because Conan was always so good on his feet. When we would do scripted pieces, Conan was great, but he sometimes considered them to be shackles. “How dare you shackle Kong!” he would sometimes say. And, in a piece like this, you could see why. When he's just totally in the moment, being his pure self and interacting with a person who’s giving him just the right thing, there’s nothing better than that. We, as writers, couldn’t compete with that at all.
Like Kevin was saying, Conan was such a history buff, especially for that era, and getting him into that outfit and using the terminology that was native to that time, Conan was so in his element.
Dorff: Jason Chillemi, our field producer, who was assisting us with all of this, obtained from the Bethpage Historical Society a glossary sheet of slang and terminology from that period. We very briefly showed it to Conan, who immediately started riffing on it before Sweeney snatched it out of his hands. That’s Sweeney’s expertise, he knew not to let Conan start pulling triggers yet.
Gordon: The goldest gold you’re going to pull out of Conan is his first instinct when he sees something. So don’t waste it in the office before the cameras are rolling.
Dorff: Conan was never going to see that sheet again until we were there on the day.
Let’s Play Ball!
Dorff: It was only about a week or 10 days later that we actually went to go do it. The people at the museum were willing to get together on a weekday and play, which wasn’t their normal thing. When we got there, everything was set to go and the guys were already playing baseball.
The first person he talked to was the umpire, who had a Nature’s Valley granola bar in his pocket, which was basically the first funny thing that happened. Then he started talking to some ballplayers. The order you see in the remote is pretty reflective of the order we went in because we watch Conan get warmer and looser as the thing progresses.
Gordon: I just watched it again over the weekend, and when he’s over by the women, you see him discover Nell. Not knowing that she’s going to be a big part of this, Conan asks all four girls about their fathers, and Nell says that hers has passed away. Then, the next time around they’re talking about their husbands and hers is off to war. You just see the delight in Conan’s face. It’s just bubbling out of him, and it just brings out the best Conan there is.
Dorff: Everything she was saying continued to arm him. Her father’s dead, her husband is in the war and “I’m not that well myself.” It all became ammunition for Conan. And, Conan just as Conan O’Brien hitting on her was funny, then him as the baseball player hitting on her was sublime. She was just an intern who worked at the museum, but she stayed in character the whole time, like a champ. She wouldn’t break.
Gordon: It would’ve been a great remote even if Nell hadn’t been there, but I do have to think the reason we’re talking about it 20 years later is 100 percent because of her and how he responded to her.
That was all improvised. The only planned thing that we did follow through on was, of course, we planned for him to change into that uniform that our wonderful wardrobe department made, plus the whole getup, the beard and stuff like that. Once he got into the uniform, one highlight, which was caught by the crew, was when there was a plane flying overhead and Conan says, “What is that demonry!?!?”
Dorff: I was going wild for the bit where Conan, as the coach, is just insulting and berating his fellow teammates. There’s this one point where a player drops a ball in the background and Conan is in the foreground. He sees this and shouts, “You ass!”
Then, at the end, we got Nell and Conan walking away, which was a wonderful way to close it.
There was no show to shoot that day so we had the whole day to do this, but the whole thing only took three or four hours to shoot. I remember on the way back — and this is the kind of thing I obsess about — I was telling Sweeney that this was awesome and how excited I was, but he wouldn’t go there with me.
Gordon: No one does a better job of not counting their chickens before they're hatched than Sweeney. He’s just going to assume the worst until he knows otherwise.
Dorff: He wasn’t saying anything, but I was just geeking out about all of it. I knew it was great.
The Final Score
Gordon: Where we earn our keep on these kinds of pieces is in the edit room. There’s just tons and tons of stuff. Obviously, we don’t do the editing ourselves — we had a fantastic editor named Liz Gross who did all the remotes in those days. She has this flair for creating the arc of a story. She had to plow through all the material, and then Kevin and I were there with her for hours and hours as we shaped the piece.
Dorff: In the piece, once Conan has made the transformation to baseball coach and player, he harangues them and harasses them and demeans them and reams them out. We had so much of that when we showed the original cut to Conan. He said, “You don’t need this much of me doing that.” We couldn’t pick what our favorite insults were.
Also, during editing, I was so obsessed for a little while that I needed to go outside and get some fresh air because I was like, “Michael, if we lose this Spanish American War joke, I’m quitting.” He was like, “You need to relax.” I was like, “I don’t want to live in a world where we don't have that!”
Gordon: I know that one big, painful thing that we had to cut was a whole long song that he sang to Nell, which, at the time, I couldn’t believe we were cutting. In the final cut, at the end, you can see a quick shot of him singing to her, but there was a whole song and it was very funny.
Dorff: After our first pass at it, Conan said, “I know we did a team photo, so get that, give it the proper treatment to make it look appropriate to the period, then call us the ‘Wabash Mashers, 1864.’”
Gordon: During the show, of course, it went over great and then this was his favorite remote for years and years. When Late Night ended, he said it was his favorite ever.
Dorff: When he said that, it felt amazing. As many stars as the system that you use allows for, give it that many stars, that’s how good I felt. I felt as good as you can feel.
