How this Brooklyn bar owner had Conan O’Brien in stitches on SubwayTakes

LISTEN | Interview with Debbie Shields:

It's not everyday you go from running a comedy night at a bar to doing improv with an Emmy-winning comedian on the New York City subway.

Debbie Shields wasn't expecting to strike up a conversation with comedian Conan O'Brien when she set out to run errands, but her quick-witted humour meant she was prepared.

"I mean, if you give it to me, I give it right back to you," she told As It Happens host Nil Köksal. 

Shields has become an internet sensation after her exchange with O'Brien aired on the most recent episode of SubwayTakes.

O'Brien was a guest on the popular internet talk show hosted by comedian Kareem Rahma, where regular New Yorkers and celebrities humorously discuss their controversial opinions while riding the subway.

• How SubwayTakes became an Emmy contender

Toward the end of his episode, O'Brien apologized to Shields as she moved into an empty seat next to Rahma. She and O'Brien shook hands and jumped into a spontaneous scene together, with O'Brien joking that the two used to be married.

Shields quickly responded that they had two kids. "One's in medical school, the other one's in jail," she said, causing the former late night host to crack up.

WATCH | Debbie Shields riffs with Conan O'Brien on SubwayTakes:

Some viewers said they loved her wit and ability to keep up with O'Brien. He was impressed, too. 

O'Brien told New York Magazine he's open to working with Shields again. "I'll do a sitcom with her," he said. "Or we can just hit the road, do a two-person show."

Shields told Köksal she'd love to collaborate with him again. Here is part of their conversation.

Debbie, what is your relationship status with Conan O'Brien now? Is remarriage in the cards? He walked out on you again?

He just did his interview and walked off the train. "Bye Debbie."

Typical. How are the kids feeling? 

They're fine. They're used to him not being around. 

In all seriousness though, how are you doing with all of this attention? 

It's crazy right now. SXM radio, I was in the New York Times, 1010 radio.

Internationally, are they interested, too? 

Yeah, somebody called me from Japan, 1:30 in the morning, Australia, England. Oh boy, it's been busy. 

On that day on the train, did you have any idea what you were walking into? 

Not at all. I was going to see my accountant for my business. 

O'Brien appeared delighted with the random encounter. (Emma McIntyre/Getty Images/SiriusXM)

Did you just see that shock of orange hair and the pasty skin? He would say that about himself, so I feel like can say that. 

No, I saw a camera crew. And when I saw the camera crew, my friend said, "Oh, that's Conan O'Brien." I was like, "Oh, OK." But I was looking for a seat because I'm always looking for a seat on the train. So I got me a seat and I told him "You hold the seat and I'm just going to go over and say hi." And that's all it took. 

And you did not miss a beat, a millisecond even. Have you always had that kind of comedic timing? 

Yeah, I mean if you give it to me, I give it right back to you. That's how it goes.

That's the New Yorker in you, I would imagine. But you are at another level, though. 

Thank you.

You didn't seem nervous, but were you at all nervous inside?

No, I was having a ball.

He was, too.

Yeah, we had a good time doing that.

You were a fan of Conan before. What about him do you like?

Yes, I like his style of comedy. He's witty, he's fast, he's risky, he is risque. I just like him. 

Did you have any idea about the show SubwayTakes?

No, I didn't know anything about that show, nothing. 

It's really cool when you meet a celebrity whose work you admire and the exchange goes really well. Sometimes, it could be not as pleasant. You go about your day, you went to your accountant. And then when did you start getting a sense that this was more than this great memory for you?

Tuesday evening. Somebody told me, "Oh, you're on Conan, we saw it." I was in my bar and people started showing me. Then Wednesday morning, it went crazy. People were calling me at eight in the morning. "Oh, you were all over the internet. You've got five million hits." Then somebody called me at like about 10 in the morning, "You're on television, on channel five. You're on channel four." And I'm like, "Oh my God." It was surreal. 

That's what I do with people, even in my bar. The name of my bar is Confessions Bar, I have comedy on Friday nights. I introduce the host of the comics and I really go off on the people. I make them laugh, I talk about their outfits, whatever it is, and they all love me. I like to see people happy. And if I lay my head to rest today, I want people to remember that I made people laugh. 

Oh, they're sure going to remember, Debbie. Conan's at the top of that list. Do you think he's going to drop by? 

He's been in touch with me. Kareem's team has been in touch with me to do another show with him. 

Oh my goodness. What would be your dream show? 

Saturday Night Live.

I think at least Conan could arrange that for you. Conan said he'd do a sitcom with you. 

Yes he would, and I would love to do one with him. 

What does this tell you about life? 

Life is funny, you never know where your blessings are coming from. That's why you have to live your life in a certain way. So when the aura of God, or whatever you want to see or call it, sees that you're doing your best and you're trying really hard and you genuine, he always throws you a ball. 

You've got the comedy night at Confessions, are you incorporating this new part of your life and your ex-husband into the bar? 

Yes, we invented a drink called Baby Daddy O'Brien. We've got whiskey, Triple Sec, lemon, lime, and blood orange. 

Can we expect you to bring your show to Toronto sometime? 

That would be fun. I love Toronto. I love Canada. I've been to Canada so many times. 

I'm sure people would love to see you riding the subway here, too, Debbie. Thank you for this. 

My pleasure. You just always laugh your ass off. 

That's the key to life.