Taylor Hill/FilmMagic
Conan would work with Debbie from 'SubwayTakes' again
Beloved former late-night TV host and comedian Conan O’Brien was a guest on a recent episode of the social media talk show SubwayTakes. The former Late Night with Conan O’Brien host, however, was outshined by a random passerby named Debbie, who has since gone massively viral on social media.
Towards the end of the episode, a woman named Debbie Shields asked permission to pass through the frame of the shot. As she did, she greeted Conan, and the pair instantly started riffing from there, joking about the family they have together.
Conan O’Brien raved about improvising with New York City woman Debbie Shields on ‘SubwayTakes’
People on social media were loving the moment given how remarkable it was to see a “regular” person go toe-to-toe with one of the great comedic improvisers of all time on Conan.
According to Debbie, she simply had to go over and greet Conan once she saw him, and may have changed her life in the process —
@snl sign her https://t.co/UzW8x8WBuy
— ktoni (@chumbwumba) October 20, 2026
“The random woman who goes toe-to-toe with Conan, one of the great comedic riffers of all time, in the final:30 of this is one of the most impressive things I’ve seen in a long time,” one viral tweet proclaimed
“Very funny to have a TV Famous person outshine an Internet Famous person like a thermonuclear bomb, and then for a random person to do the same,” a second summarized.
“He is the funniest man alive, and the 2nd funniest person alive behind the woman who sits next to him and Kareem at the end,” a third joked.
There’s really something to be said about the funniest and most entertaining clip to ever come out of this show happening when its host is completely ignored
— Eric Italiano (@ericitaIiano) October 21, 2026
Debbie, the owner of Confessions bar in Brooklyn, New York, has since been interviewed by the likes of The New York Times and New York Magazine.
Speaking to the latter publication after the clip went viral, Conan described Debbie as being an “amazing woman.”
“This amazing woman sits down next to me, and suddenly she’s throwing improv comebacks at 100 miles per hour,” he said, adding that he’s open to working with Shields again.
“I’ll do a sitcom with her. Or open a restaurant. Or we can just hit the road and do a two-person show.”
Conan O’Brien is open to doing a sitcom with the special guest from his @subwaytakes episode🤞 https://t.co/pn6ci1eldt
— New York Magazine (@NYMag) October 22, 2026
Speaking to the New York Times, Shields explained how the moment came to be.
“This was spontaneous. I had no idea. I had gotten off the A train, transferred to the F train. I was going somewhere with my best friend, Tony. And we got on the train, and we saw a little camera crew, and Tony looked over and said, ‘Hey, that’s Conan O’Brien,'” she explained.
“He’s a big fan of Conan. And I was like, ‘Oh my God.’ I said, ‘Well, you hold the seat for me, and I’m going to go sit next to him.’ So I walked up and I walked past him. I said, ‘Hey, Conan.’ He said, ‘Hey, how you doing?’ And I sat down and went on from there.”
Shields’ bar, Confessions, is located at 333 Marcus Garvey Blvd in Brooklyn. It opens at 4:30 p.m. every day, except for Sunday, when it opens at 3, and Monday, when it’s closed.