In a delightful episode of Subway Takes, comedian Conan O’Brien showcased his signature humor alongside Debbie Shields, a 68-year-old bar owner from Brooklyn. The unconventional setting—a New York City subway car—served as the backdrop for their engaging banter, which quickly captured the attention of viewers online.
A Controversial Opinion and Lighthearted Apologies
The episode took a comedic turn when O’Brien asserted that all statues should be made out of soap. This unconventional opinion led him to apologize to Shields, who was waiting to take a seat. Her gracious response, “That’s OK, Conan,” initiated a humorous exchange that quickly became a highlight of the show.
A Playful Reunion
As the conversation progressed, host Kareem Rahma playfully inquired if O’Brien and Shields knew each other. With impeccable timing, O’Brien quipped that Shields was his ex-wife, to which she quickly played along, declaring, “Yeah, we were married a long time ago.” The repartee continued to flow as Shields humorously added, “We got two kids,” leading O’Brien to ask about their well-being.
“One’s in medical school. One’s in jail,” Shields responded without missing a beat, keeping the audience engaged with her sharp wit. The duo continued their improvised routine, as O’Brien inquired whether their children still loved him despite his absence from their lives. “Your pictures are everywhere in the house,” Shields assured him, lightening the mood and further demonstrating her comedic flair.
Going Viral
Their infectious chemistry and Shields’ quick comebacks contributed to the scene going viral almost instantaneously. Reflecting on her unexpected rise to internet fame, Shields told the New York Times about her surprise at the entire experience.
Despite lacking formal improv training, Shields contributes to the comedic landscape of her Brooklyn bar, Confessions, where she enjoys hosting karaoke and comedy nights. She humorously noted that the bar’s name reflects how patrons tend to confess after a few drinks.
A Future Collaboration?
Following the episode, O’Brien expressed his admiration for Shields’ comedic timing in a conversation with New York Magazine. He stated, “This amazing woman sits down next to me and suddenly she’s throwing improv comebacks at 100 miles per hour.” O’Brien even hinted at the possibility of future collaborations, saying, “I’ll do a sitcom with her. Or open a restaurant. Or we can just hit the road and do a two-person show.”
Shields, reflecting on the encounter, remarked to the Bed-Stuy Stoop that making O’Brien laugh “wasn’t my intention.” She added, “But if you kick it to me, I kick it back,” showcasing her natural talent for quick wit and humor.
