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.

Where were you at in your careers when you were making American Pie?

JENNIFER COOLIDGE: American Pie was a huge break for me. I really didn’t have anything in my track record before it that anyone would know about, except an episode of Seinfeld, where I played Jerry’s girlfriend, and two female-driven sketch shows—She TV and Saturday Night Special, with Roseanne—and both of those failed. So I had doors that I could never open until American Pie premiered. I had a very small part, but I’m sure you feel this way, Natasha, the timing of it was unbelievable.

NATASHA LYONNE: Yeah. It’s not like it was the first teen movie sensation historically, but that was the one that started [a new trend]. Although I remember my experience of it was like deep cynicism—I think because I was a child actor. I can hear my mom at auditions telling me to enunciate, and it’s funny that later in life, my mumbling was suddenly a bonus or something. When I got the script for American Pie, I remember being very confused and offended because it seemed so normal to me. I had never had a normal high school experience. I’d only had this teen angst in Manhattan, broken showbiz-kid thing. I turned it down a bunch of times because I was like, “I don’t know how to do this.” I was really teenaged toward it. It’s a small part. I was just, like, the sidekick.

COOLIDGE: I love that you turned it down a bunch of times because that’s when they really want you.

LYONNE: My weird story with American Pie is that in the first movie—I don’t know if you know this—but I think I was the highest-paid person because I was coming off of Slums of Beverly Hills. Being a new teen actor, that was my one ingenue moment. And then, in all the consecutive movies, I got paid the least and would have the smallest part. So, they made it very clear to me that that era was over, and I really had to fight to get in them because my career was so nonexistent. I have such a bizarre relationship to that movie. Weird things would happen, like press junkets with Shannon Elizabeth—they would ask me what it felt like to be sitting next to the hot girl. And I look back and I’m like, “I was not that bad.” I was 18 and 120 and ready to rumble. I look back and I’m like, “I wasn’t even that fucking weird. I wasn’t even like some goth chick or anything.” And they made me feel like such an outsider.