Conan O’Brien Recalls Tina Fey Calling Him a ‘F—–‘ for Diaper Skit with her Husband
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Conan O’Brien recently shared a hilarious and slightly awkward moment involving Tina Fey’s husband, Jeff Richmond, on an episode of his podcast, Conan O’Brien Needs a Friend. The comedian reminisced with guest Amy Poehler about a sketch from his late-night talk show in 2001 where Richmond was made to dress up as Cupid – complete with a diaper, a bow and arrow, glitter in his hair, and no shirt.

O’Brien, now 61 years old, recounted the incident, revealing that he had no idea who Richmond was at the time. Tina Fey, also a former Saturday Night Live alum, was not pleased with the sketch and reportedly confronted O’Brien by calling him a ‘f—–‘ and asking, “What have you done to him?” While Fey’s reaction was not entirely positive, O’Brien shared that he finds the memory endlessly amusing and will always associate Richmond with being Cupid.
The skit took place during O’Brien’s tenure as a talk show host, a role he held from 1993 until he left late-night television in 2021. Despite Fey’s initial displeasure, both parties can look back on the incident with humour and fondness for the comedic chaos that ensued. Their shared history on Saturday Night Live and beyond has created a strong bond of camaraderie and mutual respect.
Tina Fey and Jeff Richmond’s relationship dates back to their early days in the comedy scene. They first crossed paths in the mid-’90s while working at Second City in Chicago. Richmond, a talented composer, and Fey, a gifted writer and performer, found success individually before joining forces at SNL, where Richmond worked on music for the show while Fey showcased her comedic prowess.
Their collaboration continued with the award-winning sitcom, 30 Rock, where Richmond’s contributions, including the iconic theme song, were celebrated with Emmy wins. Over the years, the power couple has teamed up on various projects, including Unbreakable Kimmy Schmidt and the musical adaptation of Mean Girls, showcasing their creative synergy and shared passion for comedy.
Despite Fey’s initial reaction to the Cupid skit, it’s evident that her bond with O’Brien remains strong, as evidenced by their ability to look back on the incident with laughter and nostalgia. Their shared experiences in the entertainment industry have undoubtedly forged a lasting friendship built on mutual admiration and a love for pushing comedic boundaries.
As O’Brien and Poehler reminisced about the incident on the podcast, they highlighted the absurdity and spontaneity that often define memorable moments in show business. The comedy world thrives on unpredictability, and the Cupid skit, though met with initial hesitation from Fey, ultimately added another layer to the colourful tapestry of comedic collaborations that have defined O’Brien’s illustrious career.
In the ever-evolving landscape of entertainment, where creativity and innovation reign supreme, it’s refreshing to see seasoned veterans like O’Brien and Fey continue to find joy and humour in reflecting on past experiences. Their ability to navigate the highs and lows of show business with grace and levity serves as a testament to their enduring legacy in the world of comedy and television.
Conan O’Brien and Tina Fey’s playful banter and shared memories serve as a reminder that behind the scenes of every successful show, there are countless untold stories and anecdotes that capture the essence of what makes comedy such a universal and timeless art form. As fans eagerly await the next chapter in their respective careers, one thing remains certain – the laughter and camaraderie shared between O’Brien, Fey, and their fellow comedic cohorts will continue to inspire and entertain audiences for years to come.
