It’s very difficult to match wits with a professional comedian, especially someone with the talents of Conan O’Brien.
And yet there was Debbie Shields, who turned up in an episode of “Subway Takes,” the popular internet talk show that asks celebrity guests to offer their spiciest opinions.
On the episode released Tuesday, O’Brien and the show’s host, Kareem Rahma, gabbed about an array of topics when Shields suddenly walked into the frame, bantering with O’Brien in an exchange that has delighted viewers of the video on social media.
Shields, who took a seat on the subway next to Rahma and O’Brien during their interview, lived out an aspiring improviser’s dream, getting to “Yes, and …” with O’Brien for a few moments. O’Brien started the riffing by joking that Shields was his ex-wife, to which Shields, without skipping a beat, said they had two kids.
“One’s in medical school. One’s in jail,” she said.
O’Brien, never one to miss an opportunity, asks if their children still love him, despite his lack of visits with them. Shields quipped there were pictures of O’Brien all over the house, causing O’Brien to cackle.
She joked that they had O’Brien’s hair, then said “what we don’t like, we just draw in,” about the children’s photos, causing O’Brien to crack up again.
Shields, a “proud 68” years of age, said in a telephone interview on Wednesday that she wasn’t familiar with “Subway Takes” until she stumbled upon the filming about three weeks ago, but knows O’Brien’s comedy. She is the owner of Confessions Bar in the Bedford-Stuyvesant neighborhood of Brooklyn, the borough in which she was born and raised. She opened the bar almost three years ago.
What was she doing before that?
“Well, I was living in a dumpster,” she said. “Just kidding.”
Previously, she said, she had worked in trucking and nursing.
The bar is called Confessions because, she said, “the more people drink the more they confess.”
Shields is a mother of three — but “only two kids belong to Conan,” she said.
In the interview, she discussed her brief interaction that led her to internet fame. (In an interview with New York magazine, O’Brien called her “lovely”: “I’ll do a sitcom with her. Or open a restaurant. Or we can just hit the road and do a two-person show.”)
This interview has been condensed and lightly edited for clarity.
Can you walk me through the “Subway Takes” episode? Did you actually just happen to walk on the train?
Yeah, 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.”
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.
As you probably know, the clip has gotten a lot of attention today because very few people can match wits with Conan, especially given his skill in improv. What do you think of all the attention?
It is crazy and it’s scary and it is fun and people have been calling me and I’ve been interacting with people over the phone and strangers have been calling me, giving me commendations.
Of course some people said it was pre-scripted or whatever. No, it wasn’t. Why would I be following him around? I’m a young lady from Brooklyn, Bed-Stuy. Owning a bar, working my way through life and that’s it. I don’t know Conan O’Brien.
Who was the most interesting person you heard from today?
You.
Fair enough.
And I’ve got a couple of calls from other people. Websites. Got a couple hit-ups from my neighbors and somebody that works for the mayor’s office. So it’s been really an exciting and crazy day.
Do you have any comedy background whatsoever?
Nope.
Do you have any interest now?
I just might do that, because it sounds interesting. I do own the bar and we do have a comedy night on Fridays, which is really a big thing. And I do go onstage and introduce the comedians, but that’s my limit.
And I do a karaoke night where I roast all the people that sing. Before they sing, I roast them. And after they sing, I roast them, then I give them a gag gift. And then they laugh, and that’s it.
But that’s my experience with comedy. I love to make people laugh. I love to have fun. I love to enjoy life, because life is beautiful. It’s what you make it.
Do you miss being married to Conan?
Yes, I do and as a matter of fact, I’m getting ready to hit him up for that back child support that he never paid.
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