Conan O’Brien Remembers Jeff Richmond’s Hilarious Cupid Sketch

NEW YORK, New York — During a recent episode of his podcast, Conan O'Brien reminisced about a memorable sketch featuring Jeff Richmond dressed as Cupid, specifically recalling the moment with humor and fondness.

O’Brien recounted how he encountered Richmond at an event where he was with Tina Fey, Richmond’s wife. “I was just at [ ], 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, and he played Cupid.” He described Richmond’s costume, noting, “He was in a diaper hanging on a rope with a bow and arrow and like some glitter in his hair and no shirt.”

The late-night host explained that at the time, he did not know who Richmond was. However, Fey’s reaction to Richmond’s awkward rehearsal performance left a lasting impression. “Tina had passed a monitor, and she went, ‘That’s my husband, you f—er. What have you done to him?’” O’Brien recalled, highlighting Fey’s protective instinct.

Representatives for Fey and Richmond did not respond to requests for comment from Entertainment Weekly.

During the podcast, Fey reminisced about her first guest appearance on O’Brien’s show in 2001, when she was engaged, not yet married to Richmond. At that time, Richmond’s portrayal of Cupid was less extreme than initially described, as he was simply standing in the sketch rather than suspended. “He’s an actor, and he’s actually done a few bits on your show,” Fey said. “This is who I’m marrying,” she added, humorously emphasizing her affection.

The conversation then shifted to a clip of Richmond in his Cupid costume, which included a diaper and wings, while reading the names of sexually transmitted infections. “Me and him gonna make a baby someday!” Fey jokingly remarked, eliciting laughter both on the show and from listeners.

Both O’Brien and Fey share a background in comedy, having worked at Saturday Night Live, although their paths crossed only once when O’Brien hosted the program in 2001. O’Brien contributed to the show as a writer from 1988 to 1991, while Fey began her career there in 1997 and became a featured player in 2000, a role she held until leaving in 2006.

Fey and Richmond, who met in 1994 in the Chicago improv scene, have been partners in both life and work since they married in 2001. “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,” Richmond told in an interview in 2003, reflecting on Fey’s talent.

The couple has collaborated on numerous projects over the years, including Fey’s work on 30 Rock, Unbreakable Kimmy Schmidt, and the recent musical adaptation of Mean Girls.

Richmond’s achievements as a composer are notable, with Fey securing three Emmy Awards out of 18 nominations. However, O’Brien humorously downplayed Richmond’s accolades, joking, “I don’t care what he does. He’ll get an Oscar for scoring something, and I’ll still think, ‘Heh, you were Cupid.’” The nostalgia and camaraderie between these comedic icons shine through their shared stories and laughter.