Allow Conan O’Brien to Introduce You to Chris Fleming

Chris Fleming built his following one hyper-specific, unhinged YouTube video at a time. Starting with his breakout web series Gayle, where he played a middle-aged suburban mom worrying about Christmas cards and a shoes-off house, Fleming spent the better part of a decade building a cult following through sheer, compulsive output, moving from YouTube specials to Peacock and now, finally, to HBO. His comedy, dense with New England pathology, suburban mom archetypes, and references so particular they feel almost made up, is on full display in Live at the Palace, an acrobatic hour of comedy that somehow gets bigger the more specific it gets. Someone who’s been watching Fleming for years is Conan O’Brien, who, not coincidentally, executive produced the special. We got the two northeasterners together to talk about it, and the rest took care of itself.

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CONAN O’BRIEN: I want to begin by expressing some astonishment. I thought this was an interview with illusionist Doug Henning. And he died in 2000 and I went to his funeral, so that’s on me.

CHRIS FLEMING: Have you seen this magazine?  Usually this is like Alexander Skarsgård interviewed by Judge Judy. It’s Fiona Apple interviewed by the Tinder Swindler. But you and I actually make sense together.

O’BRIEN: This makes sense because I have a hard time imagining who I can relate to more than Mr. Fleming here. You’re a ridiculous figure. I’ve been enamored with you for a long time, and still, I wish I was talking to the late illusionist, Doug Henning.

FLEMING: The last I saw you was when you catcalled me at that stop light about a week and a half ago.

O’BRIEN: I was in my car.

FLEMING: I think your vanity plate said, “Redheads have more fun.” 

O’BRIEN: I have the longest license plate in Los Angeles. It’s actually illegal. It’s good to see you.

FLEMING: It’s good to see you. I loved you coming in those glasses, by the way, looking all scholarly.

O’BRIEN: I’m not afraid to put on some Jacques Marie LaMage glasses every now and then.

FLEMING: You look like Sissy Spacek in Carrie when you take them off.

O’BRIEN: [Laughs] That’s my actual face. 

FLEMING: I’m in Northampton right now. Do you understand that? 

O’BRIEN: I could tell immediately that you were back in the Northeast where you and I come from.

FLEMING: I’m in a more vegan area than where we’re from. If the people in charge of the Salem Witchcraft trial saw Northampton, they’d be pissed.

O’BRIEN: [Laughs] This is how big you’ve become, Chris. As you’re talking to me, I can see on this Zoom, a bear just walked by and recognized you. 

FLEMING: I literally saw a porcupine! Did you know there’s porcupines in Massachusetts?

O’BRIEN: I hear there’s also turkeys in Boston running around. That’s a real thing.

FLEMING: Yeah. I saw you talking to Charli XCX looking like an undercover cop, by the way. 

O’BRIEN: [Laughs]

FLEMING: I saw you resisting the urge to bring up The Moody Blues.

O’BRIEN: [Laughs]

FLEMING: I saw you stepping on a tack in your shoe to not talk about Zydeco with Charli XCX.

O’BRIEN: I thought I did a great job pretending to be cool. 

FLEMING: Do you understand that we’re so afraid of those people, but they want to be near you?

O’BRIEN: No, they don’t. It’s been confirmed that Charli XCX did not want to be with me. I really drilled down on this with her people, and they said, “Trust me, we had to force her into that room with what she thought was an old scarecrow lady.” Speaking of scarecrow ladies, I have to talk about you, Chris, because you’re the focus here. From the moment my kids came to me years ago and said, “The funniest thing right now is this guy on the internet who pretends to be this Lady Gayle,” and I started watching, I needed my daily fix of Chris Fleming.

FLEMING: A drip.

O’BRIEN: It was a drip at first, but now I need three IVs. And I just love the new special. 

FLEMING: I’ve been waiting to hear that. Did you really?

O’BRIEN: What are you talking about? I adore the special because you’re up to your old high jinks.

FLEMING: My old tricks.

O’BRIEN: I can see you took my advice. I told you long ago, “Don’t move around so much.”

FLEMING: Stay still.

O’BRIEN: I said, “I want you to wear very masculine, working class clothing.”

FLEMING: You gave me a Men’s Warehouse gift certificate, and you whispered in my ear, “Stillness is king,”

O’BRIEN: And I said, “Make sure the references are accessible to all age groups. That means none of your Trader Joe’s marginalia, no takes on NPR.”

FLEMING: You wanted Big Dig material. 

O’BRIEN: And I insisted that you talk at length about the 1975 Red Sox and bring up Fred Lynn repeatedly, and you said, “Got it.” And then to my surprise, I tune in and you’re up to your old high jinx. You imp.

FLEMING: With panty lines showing, too. 

O’BRIEN: I don’t know anyone who has more specific references, comes up with them more quickly, and is more prolific about things I’ve never thought about. Sometimes you’ll throw out a reference and the crowd is going crazy and I resist the urge to feel desperately old and out of it.

FLEMING: I had a manager who said, “I don’t know what you’re talking about 90% of the time.”

O’BRIEN: [Laughs] You have established a rhythm that’s completely yours. You lull people into this state where suddenly they know everything about the specific guy who’s serving you a boba tea and we all are just there with you, even though I shouldn’t know what you’re talking about because I’ve never had boba tea in my life.

FLEMING: You haven’t?

O’BRIEN: It’s a doctor’s order. It would kill me instantly.

FLEMING: What’s your vice right now? Coffee?

O’BRIEN: That’s really kind of you.

FLEMING: Well, I know the first time we do cocaine, we would die. 

O’BRIEN: I don’t do any of those drugs. I ingest a ton of illegal acne medication. Okay. We need to come clean. We’ve been friends for a number of years now. I didn’t even know you well enough to do this, but the first time I saw you, I grabbed you and started manhandling you to throw you out of the room you were in. You immediately became this electrified gelatin skeleton that was flopping around. Then that became what we do. You’ve been over to my house a bunch of times, and the minute you come through the door, I grab you and eject you from the house. 

FLEMING: Drag me down and throw me into Larry David at the door who then says, “I think I got here too early.”

O’BRIEN: [Laughs] My favorite part of this was that maybe two years ago I was attending South by Southwest, and I guess you had done your show somewhere. You don’t know it, you’re just pulling up to a hotel, and  I happened to be waiting in front because I’m going to leave.

FLEMING: My heart drops.

O’BRIEN: But you don’t see me. The door opens, you get out of your car, you’re just trying to go into the hotel because you’re tired and suddenly I march, with no hesitation—

FLEMING: No greeting. No salutation.

O’BRIEN: I grab you and I start dragging you down the driveway of the hotel. Everybody’s looking. They think Conan caught some kind of a crane that found a wig.

FLEMING: Security saw it happening and obviously they’re going to help you, so they started coming at me while I was trying to wriggle free.

O’BRIEN: Security started to intervene on my behalf.

FLEMING: You haven’t even said hi to me yet. You’re just saying, “I told you to stay out.” 

O’BRIEN: Seriously, usually when I watch something, my wife, she often doesn’t want to watch the thing that I’m watching.

FLEMING: Because you’re watching Ken Burns deleted scenes.

O’BRIEN: [Laughs] But she was delighted when she found out that I was getting an early copy of your special.

FLEMING: What did she think?

O’BRIEN: Loved it. And then she FaceTimed our daughter who’s at college and held the phone up to the screen and of course you were on all fours behaving like an absolute fool. And then I see her face on the phone erupting in joy.

FLEMING: You know what I was thinking about you, Conan? Everyone that knows you talks about how you are the most comfortable public person that is among us. You don’t mind being seen. You cherish it.

O’BRIEN: I’m always the same, for the most part. My assistant is here listening to this and he’s nodding because he knows that I’ll riff with someone on an abandoned street corner for 25 minutes until they say, “Conan, I have to go.” It’s one of those ying yang things where it’s sad and sweet at the same time.

FLEMING: Did you become super famous in your 30s?

O’BRIEN: I had just turned 30 when I became known to all.

FLEMING: The later, the better.

O’BRIEN: I don’t know. I think it’s also just my nature. I can’t even analyze it. I like talking to people and finding out what their deal is. I think I’d be the same way if I wasn’t a known person. 

FLEMING: You’d probably be crazier because you wouldn’t have an outlet. 

O’BRIEN: I’d be grabbing people.

FLEMING: But you still are.

O’BRIEN: Yeah. There’s going to be some real information in here. Describe the 14-year-old Chris Fleming or the 16-year-old Chris Fleming. Are you a theater maven?

When I was 16, I was the Scarecrow in a local production of The Wizard of Oz, which got me out of so many speeding tickets in my town. 

O’BRIEN: Is that true?

FLEMING: Because the cops were like, “You took a picture with my daughter as the Scarecrow.”

O’BRIEN: That’s so nice.

FLEMING: Yeah. What were you doing? I saw a clip of you interviewing your sister, I think, at 16.

O’BRIEN: I was much younger than 16. I was working on my timing. 

FLEMING: You always wanted to interview people?

O’BRIEN: I liked being funny when I was a kid and used to dream about getting to be funny in a bigger capacity, and then totally gave it up because I thought, “It’s the 1970s. Gerald Ford is president. He’s wearing these “Whip inflation now” buttons. The snow is always gray.”

FLEMING: The hopelessness of the dirty snow.

O’BRIEN: And I thought, “I don’t know anyone in show business. That’s not a real thing I could ever do.” So I just started to be a grind because I thought, “Well, that’ll get me someplace.”

FLEMING: Wait, what’s a grind?

O’BRIEN: Someone who’s like, ” I better go study my books so I can elevate myself and get out of this tightly packed family where no one knows my name.”

FLEMING: That’s because you were smart. I was just delusional. I thought that even if I stayed in Stowe, that I would be so famous in Stowe.

O’BRIEN: Delusion, though, is so helpful. Just today, Judd Apatow found a clip of me from 1986. I’m in the background at some comedy event that he’s doing a documentary about.

FLEMING: Oh, I didn’t know he did documentaries.

O’BRIEN: [Laughs] It’s a documentary about the time he stopped doing documentaries, briefly. But he said, “Hey, I think I found you.” And sure enough, it was the first Comic Relief, and there in the background is me.

I’m working there as an intern out in L.A. I had just arrived, and I look about 14 years old. I have to say this. I get very giddy when I watch you do your thing. I get real giddy because you’re playing some part of the fret on the guitar that I really enjoy. It’s still a mystery to me. When you were doing that thing about women, what was it? Women can see things that…is  it Trader Joe’s?

FLEMING: Oh, snacks at Trader Joe’s.

O’BRIEN: Yes. There are snacks at Trader Joe’s that only women can see. You have these ideas that get my brain kind of giddy, like I’ve just taken a gummy, which I’ve never tried, by the way. And here’s the thing. When people make comedy, they really should be just making it for themselves.

FLEMING: Yes.

O’BRIEN: That’s what SCTV did. That’s what Monty Python did.

FLEMING: Yep.

O’BRIEN: That’s what we were trying to do in the early years of Late Night.

FLEMING: Conan, you’re obviously the template for all this insanity.

O’BRIEN: Oh, don’t blame me.

FLEMING: I am. That’s the interesting thing about being a person, is you write things and you think, “Oh, no one’s going to get this.” But if it comes from a person’s mind, there will be people who like it. 

O’BRIEN: There was another era where there were three networks and almost no opportunity for someone like you or me to get to be ill on television. And then god bless Silicon Valley, they invent what they think is a way for everyone to do our taxes in our own office. What they didn’t know was that they were weaponizing people like you and me.

FLEMING: They were making a playground for undiagnosed personality disorders to run free.

O’BRIEN: That’s how I found you. You were not making your videos because you wanted to get a family sitcom instantly. You were doing this because you couldn’t help it.

FLEMING: Yeah, it was compulsion.

O’BRIEN: Now you have these huge sold-out venues and you think, “What a wonderful misuse of a beautiful technology.”

FLEMING: That is so good. You’re so right.

O’BRIEN: It’s true. When are we hanging out again? 

FLEMING: I’m coming back next week if you want to hang.

O’BRIEN: Yeah, let’s hang out. I want to meet you outside a public place and manhandle you in front of everyone.

FLEMING: Let’s go to a basement somewhere. You can just throw me around.

O’BRIEN: Well, I think we’re going to cut this off and I’ll tell you why. I honestly thought that this was going to be a chat with Doug Henning, the long dead illusionist from Canada. And again, no disrespect to him, but I was so excited to have a chat.

FLEMING: Yeah, I get that.