Conan O’Brien recalled a hilarious moment when Tina Fey reacted angrily to her fiancé Jeff Richmond’s absurd Cupid costume in a 2001 Late Night sketch, revealing the behind-the-scenes dynamics and humor of their close relationship.

In a recent episode of Conan O’Brien Needs a Friend, the beloved comedian Conan O’Brien shared a hilarious and somewhat awkward story from the early 2000s involving Saturday Night Live star Tina Fey, her husband Jeff Richmond, and a revealing sketch that left Fey visibly upset.

The story centered around a bizarre and embarrassing moment during a 2001 segment on Late Night with Conan O’Brien, where Richmond, a composer and musician, was dressed in an almost absurd Cupid costume, which included a diaper, a glittery wig, and no shirt as he was suspended on a rope.

O’Brien, who was speaking to fellow comedian Amy Poehler on the podcast, recounted how Fey, who was engaged to Richmond at the time, walked by a monitor during the rehearsal and caught sight of her future husband’s disheveled and revealing outfit.

According to O’Brien, Fey, shocked and annoyed, responded loudly and humorously: “That’s my husband, you f—er. What have you done to him?” Fey, known for her quick wit, didn’t mince words as she took in the sight of Richmond’s ridiculous look.

The moment was undeniably awkward, but O’Brien, always the storyteller, highlighted the humor in the situation. At the time, O’Brien didn’t even know who Richmond was, as they hadn’t yet fully connected on a personal level.

O’Brien jokingly shared how he was unaware of the close relationship between Fey and Richmond, which made her fiery reaction all the more entertaining to him.

Richmond, who was fully embracing the absurdity of the moment as Cupid, went on to read a list of sexually transmitted infections as part of the ridiculous sketch.

Despite the over-the-top nature of the scene, the situation became a catalyst for some of the funniest behind-the-scenes stories, particularly when it came to Fey’s protective response to her fiancé being thrust into such an outlandish and awkward role.

The sketch, which would have been an unusual segment in itself, ended up being a memorable moment not only because of its content but because of the reaction it elicited from Fey.

Conan’s retelling of the story on his podcast was full of laughs, but it also underscored the deep affection and camaraderie between the trio of O’Brien, Fey, and Richmond.

As many know, Fey and O’Brien have shared an extensive history, starting from their time working together on Saturday Night Live.

The pair formed a friendship that lasted through their professional collaborations, including Fey’s time as the head writer and O’Brien’s tenure as a cast member and later, the host of Late Night.

Their mutual respect and friendship have only strengthened over the years, with their occasional collaborations continuing to delight audiences.

The story of Fey’s reaction to the Late Night sketch also gives a glimpse into their personal relationship. Despite the initial frustration, Fey’s protective response was clearly a testament to how much she cared for her fiancé, even in the most ridiculous of circumstances.

Richmond, on the other hand, seemed unfazed by the absurdity of the role and fully embraced the humor of the sketch.

His involvement in the segment was also a reflection of his long-standing role as a collaborator on the show, working behind the scenes on musical compositions and occasionally making appearances in sketches.

Looking back on the moment, O’Brien has often mentioned how remarkable it was to witness such a raw, unfiltered reaction from Fey, who had no qualms about speaking her mind in defense of her future husband.

Even though the moment might have caused some initial tension, it only added to the humor and depth of the relationships that had been built over years of working together.

Despite her initially angry reaction, Fey and O’Brien have shared countless laughs over the years, and Richmond has since become an integral part of their shared history.

In the years that followed, Fey and Richmond’s relationship continued to grow, and they eventually married and had children together.

Richmond’s role in the world of comedy and television also flourished, with his musical compositions continuing to be a hallmark of many successful shows, including 30 Rock, which was created and starred Fey.

O’Brien, meanwhile, moved on to his own success, leaving Late Night and later hosting Conan for TBS, where he continued his entertaining interviews and insightful comedic commentary.

The sketch incident, while humorous and potentially awkward at the time, only serves to highlight the deep and longstanding bond between O’Brien, Fey, and Richmond.

Their shared experiences, whether behind the scenes or in front of the camera, have contributed to some of the most memorable moments in comedy.

O’Brien’s retelling of this story on his podcast is a testament to the tight-knit relationships within the comedy world, where jokes, awkward moments, and genuine affection often go hand in hand.

Looking back, Fey’s reaction to her fiancé in a ridiculous Cupid costume is one of those behind-the-scenes moments that made the comedy world feel even more personal and relatable to fans.

It’s a hilarious reminder that even the most accomplished stars are just people, dealing with moments of embarrassment, frustration, and—of course—plenty of laughter.

As O’Brien, Fey, and Richmond continue to contribute to the world of comedy and entertainment, their friendship and shared experiences remain as strong as ever, providing fans with endless stories and fond memories from their years of collaboration.