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Natasha Lyonne and Jennifer Coolidge Reunite Two Decades After ‘American Pie’

Apart from having captivatingly good series in the current Emmy race—and two of the more memorable speaking voices on television—Jennifer Coolidge and Natasha Lyonne share a distinction that should delight trivia experts: They both appeared in 1999’s teen sex comedy American Pie. Lyonne played the wisecracking, scene-stealing high schooler Jessica, who at one point acts out an orgasm in the halls of East Great Falls High. Coolidge was Stifler’s Mom, a fantasy figure for the virginal high school boys in the movie, as well as the reason the term “MILF” entered the mainstream lexicon and never went away.

A cultural phenomenon that inspired a wave of raunchy comedies, American Pie was very much a product of its era—more interested in male characters than female ones—so Coolidge and Lyonne didn’t get the screen time they deserved. But after a series of ups and downs, they’re now doing some of their best work and claiming a power for themselves that wasn’t on offer 20 years ago. As part of V.F.’s ongoing Reunited series, which brings actors together years after they shared the screen, I spoke to Coolidge and Lyonne about lives past, present, and future.

Both actors spent their 20s in New York, struggling not just with their careers but with substance issues that landed them in rehab. Both had a difficult time breaking out of the boxes their industry put them in. But Hollywood, and especially TV, has evolved over the years. Last year, Coolidge starred in the first season of HBO’s The White Lotus as Tanya, a wealthy, directionless woman who travels to Hawaii to spread the ashes of her recently deceased mother. Creator Mike White is a friend of Coolidge’s, and the role he wrote for her allowed her to reveal a more dramatic side that’s actually been there all along. Lyonne plays a woman whose mother also haunts her in many ways on Netflix’s Russian Doll, which recently launched its second season. Lyonne cocreated, cowrites, and often directs the show, and it is inspired by her own experience with addiction. She stars as Nadia, a woman who, after pulling herself out of a time loop in the first season, finds herself journeying to the past (via NYC subway) to right an ancestral wrong.

Lyonne popped onto the video call from Los Angeles with a cigarette dangling from her mouth. Coolidge, now filming the second season of The White Lotus, logged on from Sicily.

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