For comedy fans of a certain age and taste, first encountering Late Night With Conan O’Brien was something close to a religious experience. The show was filled with surreal and often nonsensical characters that, decades later, still feel like nothing else on television: the Masturbating Bear, the FedEx Pope, Preparation H Raymond, Vomiting Kermit, the revered Triumph the Insult Comic Dog—it’s a long list.
One of the most iconic ’90s sketches featured Stacy, the Conan-obsessed younger sister of Late Night sidekick Andy Richter. She was played by soon-to-be comedy giant Amy Poehler, a co-founder of the improv and sketch group Upright Citizens Brigade and the future star of both Saturday Night Live and Parks and Recreation. And every one of her many appearances, starting with the first in 1997, became a hall-of-famer, as Poehler transformed into the very embodiment of hormonal, early-teen awkwardness, oscillating between shy glances at her crush and unrestrained aggression toward her teasing older sibling.
In a recent installment of his Conan O’Brien Needs a Friend podcast, the host praised Poehler’s performance, particularly one appearance that showcases how “fearless” she was—and remains—as a physical comedian.
“The running joke was you have a crush on me, and I’m always trying to politely explain that I’m [too old for you],” O’Brien says in the clip. “Then you think Andy’s getting in the way, and you attack Andy. You would give these great speeches. … If the joke called for you, as Andy’s little sister, to go charging down the aisle and leap and hit him so that he falls over, [you would].”
The podcast includes a segment from one classic sketch, cutting straight to the climax, with Stacy fed up with Richter’s ridicule. “Alright, you know what?” she says from the audience. “It’s judgment day, bitch!” She then races to the stage and tackles a seated Richter, who pleads at the last second: “Stacy, don’t do this!” She then hops onto O’Brien’s back, pleading, “I love you” as he flails around. Reflecting on that scene, O’Brien calls the reaction “one of the biggest laughs I’ve heard in-studio.”
Poehler admits that it was a “good jump” and praises early Late Night writer Brian Stack for his work on the sketch. O’Brien adds, “We would give you a script that was like, ‘Eh, that’s a solid B,’ and you would take it to an A++++++. It was insanity, and I never took that for granted. Now I look back on it, and I’m like, ‘I got to have Amy Poehler do bits on my show?’”
Her physical-comedy genius brings O’Brien to another point: that, historically, women haven’t always been empowered to make those kinds of choices. “I hope it’s not still the case,” he says, “but, long ago, there used to be a sense that women don’t… [that] ‘you’ve gotta be ladylike.’ I remember my mom being a little bit that way. If I’m being completely inappropriate, it’s funny. If one of my sisters was doing it, it was, ‘Now, hold on.’ It was a thing. She came from a very traditional Irish Catholic background where ‘you’ve gotta be a lady.’”
Poehler says that, growing up, her dad “instilled a lot of confidence and almost a hustle that didn’t feel very gendered at the time.” She continues, “Both of my parents were very funny, and there was a lot of encouragement to speak my mind, to kind of be a little bit of a challenger.”
In a 2021 Washington Post retrospective rounding up some of O’Brien’s best TV moments, Stack picked this sketch—the first he ever wrote at Late Night—as his favorite memory.
“Amy took my very simple idea about a 13-year old girl with pigtails and braces having an unrequited crush on Conan and knocked it totally out of the park with her hilarious performance, running the gamut from adorable bashfulness to volcanic, homicidal rage,” he said. “I’d known Amy back in our Chicago improv days, and I’ve always been in awe of her incredible talent, but seeing her, Conan, and Andy [Richter] have so much fun in that sketch is an especially wonderful memory for me and I’ll never forget it.”
