W/T: Debbie Shields Went Bar-For-Bar With Conan O’Brien On ‘Subway Takes,’ and The Internet Went Crazy
A Brooklyn bar owner’s quick wit on the trending “Subway Takes” has social media users praising her improv skills and wondering if her true calling is in comedy.
New York City’s subway system is known for its unexpected moments, but Brooklyn bar owner Debbie Shields got more than a regular train ride when she found herself going head to head with jokes with comedy legend Conan O’Brien.
During an appearance on Kareem Rahma’s “Subway Takes,” Shields delivered a slate of hilarious improv comebacks that left O’Brien laughing and social media calling for her to be the next comedy sensation.
If you’ve ever stumbled on the show, you know the series puts everyday New Yorkers and celebrity guests on the spot to share their hot takes, but Shields’ impromptu exchange proved she could go against a comedy heavyweight.
Related Content: A New Crop of Black Comedians You Should Know
O’Brien shared the unexpected encounter in an interview with New York Magazine, explaining that the segment was nearly over when Shield took a seat on the train.
“We were shooting ‘Subway Takes,’ it was going really well,” O’Brien shares with New York Magazine. “We thought we had everything and we were just about to end when this amazing woman came and sat down next to me and suddenly she’s throwing improv comebacks at 100 miles an hour.”
Shields, who had no idea she was about to become part of the show, quickly found herself going bar for bar in jokes with O’Brien while Rahma had a front-row seat.
“We go way back. We were married a long time ago,” O’Brien jokingly shared with the host.
“We got two kids, by the way…” Shields adds.
“How are they by the way, I haven’t visited,” O’Brien asked.
“They’re fine. One’s in medical school. The other one’s in jail,” Shields responded.
“I’m sorry. I haven’t sent any money.” O’Brien said as Rahma held the mic to Shields.
The conversation continues as Shields reassured O’Brien that their fictional children were doing well, despite him not contributing a dime to their upbringing.
“They still love me?” O’Brien asked.
“Pictures are everywhere in the house.” Shields pointed out.
The witty comebacks just kept coming.
“You were my happiest marriage,” O’Brien said, turning to Shields. “That was the best year and a half of my life.”
Shields quickly fired back.
“I’m trying to tell you. I’ve heard that from my other three husbands, too.”
Oh, she was on fire!
This viral interview drew massive attention on social media, with folks praising Shields’ comedic timing and calling for her to pursue comedy. Shields told NBC Nightly News she was just looking for a seat and didn’t expect the conversation.
“I’ve seen some crazy things on the subway but this was really the craziest for me,” Shields said. “This was never planned, I had no idea. I’d never even seen the show.”
The “Confessions Bar” owner said the attention unexpectedly changed how people interact with her. After experiencing people being rude to her, she began receiving autograph requests. She even named a drink after him called “Baby Daddy O’Brien.”
Shields had one final message for the late-night comedian: “Tell Conan I said send that child support.”
And he better send it!
He even floated the possibility of working together on a sitcom, opening a restaurant, or hitting the road for a two-person tour.
Meanwhile, social media kept celebrating Shield’s unexpected viral moment.
“She went bar to bar with the goat.” one TikTok user wrote.
Another commenter was impressed by how seamlessly Shields held her own.
“Wait wait wait,” another wrote. “She really went total improv with a professional with no prep? Is she looking for acting work or nah?”
And a third wrote: “This is a literal masterclass. Didn’t pause or break for a second. Just ate up an entire scene with a comedy legend like it didn’t even matter.”
