express gazette logo
The Express Gazette
Tuesday, October 27, 2026

Conan O'Brien and Brooklyn Bar Owner Plan Karaoke Reunion After Viral Subway Encounter

The comedian and Debbie Shields, whose humorous subway exchange went viral, are considering future collaborations.

US Politics • 2 hours ago
Conan O'Brien and Brooklyn Bar Owner Plan Karaoke Reunion After Viral Subway Encounter

The Brooklyn bar owner who shared a viral subway moment with Conan O’Brien is open to future collaborations with the comedian, including a possible karaoke session.

Debbie Shields, owner of Confessions Bar in Bed-Stuy, told The Post that O’Brien has reached out since their impromptu conversation on the subway, which was captured and shared online. They are discussing potential future interactions, which could include a visit to her bar.

Shields, 68, became an internet sensation after her quick-witted banter with O’Brien during an appearance on the “Subway Takes” web series. In the viral clip, she humorously claimed to be the comedian’s “baby momma” and joked about their shared children, who she said inherited his signature hairstyle.

The encounter occurred when Shields was riding the F train and her assistant pointed out O’Brien being interviewed by the show's host. Shields, seeking a seat, then joined the conversation.

Despite having no formal comedy training, Shields' natural improvisational skills impressed viewers, and the video has garnered millions of views. Her bar, Confessions Bar, which she opened two years ago, has seen a significant increase in customers since the video went viral.

Exterior view of Confessions Bar in Brooklyn, owned by Debbie Shields.

Customers have flocked to the bar, some seeking out a specially created cocktail named the “Baby Daddy O’Brien.” The drink features Irish whiskey, a nod to O’Brien’s heritage, and an orange slice garnish to represent his hair.

Shields described her personality as one that naturally seeks to make people laugh, a characteristic she feels has helped her navigate life and her business.


Sources