Conan O’Brien has never been one to back down from a joke, even when it involves a friend’s husband. 

On the March 10 episode of his podcast, Conan O’Brien Needs a Friend, the legendary comedian reminisced 

with guest Amy Poehler about some of their funniest past moments. 

One particular memory stood out—an old sketch involving Tina Fey’s husband, Jeff Richmond, which O’Brien joked may still require an apology.

Jeff Richmond’s Unforgettable Role as Cupid

While recalling his time at Saturday Night Live (SNL), O’Brien, 61, shared a story about running into Fey and her husband, Richmond. 

The encounter immediately brought back memories of a 2001 sketch on his talk show, where Richmond played Cupid—a role that may have left a lasting impression on both him and his wife.

“I was just at SNL and I saw Tina with her husband Jeff Richmond,” O’Brien said. “And I’m sorry, Jeff, but I immediately go to when we first used Jeff Richmond, who’s very brilliant and incredibly successful, he played Cupid.”

In the sketch, Richmond appeared wearing nothing but a diaper, a bow and arrow, and some glitter in his hair. Suspended on a rope, he awkwardly spun around during rehearsals—an image that still cracks O’Brien up to this day.

Tina Fey’s Hilarious Reaction to the Sketch

At the time, O’Brien admitted that he wasn’t familiar with Richmond’s identity. However, Fey quickly made sure he knew exactly who the man in the Cupid costume was.

“Tina had passed a monitor and she went, ‘That’s my husband, you f—–. What have you done to him?’” O’Brien recalled.

Despite Fey’s reaction, O’Brien has no regrets about the sketch. “I don’t care what he does — he’ll get an Oscar for scoring something, and I’ll still think, ‘Heh, you were Cupid!’” he joked.

The Love Story of Tina Fey and Jeff Richmond

Fey and Richmond had only been married for a short time when the Cupid sketch aired. The couple tied the knot in 2001 after dating for seven years. They first met in the mid-’90s while working at Second City in Chicago—Fey was an improv performer, and Richmond was a composer.

Richmond was immediately struck by Fey’s comedic talent. “I don’t want to say she was funny ‘for a woman,’ but there were so many talented men there at the time, and then suddenly there was Tina, who was so funny — and she was at home with all those boys on the stage,” he once told The New Yorker.

Their journey together eventually led them to SNL, where Fey worked as a writer and performer, while Richmond became a composer and music director.

A Power Couple in Comedy and Television

Over the years, Fey and Richmond have collaborated on several major projects, including the critically acclaimed sitcom 30 Rock. Richmond composed the show’s iconic theme song, which won him three Emmy Awards.

In a 2018 interview with The Hollywood Reporter, Richmond spoke about their creative dynamic on 30 Rock:

“On 30 Rock, we would be not necessarily occupying the same creative spaces all the time. She would be writing the script, and then I would be off in another room writing the songs … [I]t was very enjoyable!”

The couple continued their successful partnership with projects like Unbreakable Kimmy Schmidt and the Broadway adaptation of Mean Girls, further proving that their professional and personal lives blend seamlessly.

No Hard Feelings, Just Endless Laughter

While the Cupid sketch may have caught Richmond off guard at the time, it remains a hilarious moment in O’Brien’s career. As for Fey, even if she was shocked back then, she and Richmond have long since moved on—continuing to thrive as one of Hollywood’s most beloved creative couples.

And as O’Brien made clear, no matter how successful Richmond becomes, he will always be remembered for that one fateful moment—dangling in a diaper, playing Cupid on late-night television.

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