A star is born? In a video shared on Tuesday, Conan O’Brien was in the middle of sharing his piping-hot opinions (statues should be made of soap, celebrity interviews should be done the old-fashioned late-night way) with SubwayTakes host Kareem Rahma when 68-year-old Debbie Shields walked into the frame and sat next to them on the train, saying hi to the former late-night host and shaking his hand. O’Brien started improvising, explaining that he and the woman “go way back” and “were married a long time ago.” Then, without missing a beat, she replied, “We got two kids.” What followed was a masterclass in improvisation: Shields played along with O’Brien’s jokes and kept the bit going, saying one of their kids is in medical school and the other is in jail. She said that despite O’Brien not being a present father or contributing in any way, the kids still love him. “Pictures are everywhere in the house, don’t worry,” she said, causing O’Brien to break into a full-bodied laugh.
That’s how Shields, who, up until the release of that interview, was a complete stranger, became a breakout star. Shields only showed up near the end of the full SubwayTakes video, but the clipped version posted on social media smartly included her cameo and turned her into a viral sensation, with people saying that she should be on Saturday Night Live or be in show business in some form. O’Brien, for his part, told New York Magazine, “She needs to get all the credit in the world. She’s lovely. She’s fantastic.” When the interviewer suggested they team up for a two-hander, like a buddy comedy, O’Brien said he was all in. “I’ll do a sitcom with her. Or open a restaurant. Or we can just hit the road and do a two-person show,” he said, suddenly remembering Shields mentioning she owns a bar. “All I want is some free drinks at that bar. That’s my way of saying thank you, is demanding that she give me free drinks.”
Since the interview went viral, Shields, who owns a bar in Bed-Stuy, Brooklyn, has spoken to several publications, including The New York Times and Vulture. Shields said that she doesn’t have a background in comedy, but she’s always had a knack for making people laugh and liked O’Brien’s humor. She also shut down speculation that the banter was so effortless it must have been staged, saying she was simply transferring trains when her best friend pointed out O’Brien. Being a fan, Shields walked over to greet him, and the rest is history. “Why would I be following him around?” she told The New York Times. “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.”