After nearly three decades in Hollywood, Rachael Leigh Cook is still perhaps best known as Laney Boggs—the anti-establishment heroine at the center of the 1999 teen flick She’s All That. In it, Cook famously trades paint-splattered overalls and a falafel hat for a red dress and romance with Freddie Prinze Jr.’s prom king.

But when Cook got a call from producer Jennifer Gibgot about Netflix’s He’s All That, a gender-flipped remake starring TikTok’s Addison Rae (who wasn’t even born when the original was released), she had an inkling what Gibgot would say. “My mind went to, She’s going to say the mom. I’m fine with that. I am a mom,” Cook recalls in a recent Zoom with Vanity Fair. “Sure enough, she said, ‘We want you to play Addison Rae’s mom.’ I said, ‘Who is that? Because I’m not cool.’ All you have to type in, I think, is ‘a-d-d’ into Google, and you learn a lot.”

This wasn’t the first time Cook had been approached about an update on the ’90s rom-com; a previous planned remake with producer Tonya Lewis Lee never materialized. Yet reimagining the movie that gave Cook her big break proved daunting. “I wasn’t sure how I felt about wanting to be involved because it might seem like, Am I trying to play the hits again well after the fact? Am I trying to set myself up in a position of being actively compared to my younger self?” Cook explains. “That seems like a terrible idea.”

Despite her trepidation, Cook signed on and found herself reconsidering the ebbs and flows of her own career. Ahead, Cook reflects on that memorable staircase scene in She’s All That; how her other Y2k-era cult classic, Josie and the Pussycats, unjustly flopped; and why she decided to reenter the rom-com landscape.

Vanity Fair: What was your initial reaction to He’s All That (out August 27)—were there reservations on your part?

Rachael Leigh Cook: I definitely had my share of reservations about it because, to put it simply, this movie ended up being a way bigger touchstone in my life and career than I ever thought it was going to be. I don’t mean that as any slight to the movie, but it’s still the main thing that when people walk up to me in the frozen food section and want to say hello, they usually want to talk about She’s All That. So in that sense it’s very special to me and it is kind of sacred. But ultimately I decided that rather than being asked how I felt about He’s All That for, plainly, the rest of my career, I would rather just be visibly supportive and forward-facing about my endorsement of the movie, as it were.

You were around the same age as Addison when you filmed She’s All That. Was there advice you gave her about navigating the industry?

It didn’t really feel like there was a moment, especially in COVID. It would’ve been pretty awkward for the O.G. that has been trotted out to try to sit you down and espouse life advice. But the truth is that there’s a lot that I wish I had known when I was coming into my own in the industry. The unfortunate truth is that you have to figure out a lot of these things on your own. 

Where Addison especially is from, it’s a built-in, very legitimate industry. She can treat acting like a side-hustle if she wants to. That’s the most personally empowering way that you could approach being an active participant in the industry: treating it like you don’t need it. In terms of advice, I would say, just keep working hard and know where you want to go, because when people ask you what you want to do next, it’s very important to have an answer. That’s definitely a mistake that I made. I thought that I could just say, “Hey, what interesting opportunities do you have? I’m a fan of this thing I’ve heard of called good writing. Do you have some of that?”

The She’s All That cast has gone on to do incredible things—from Gabrielle Union to Kieran Culkin to the late Paul Walker. What are your memories from working with them?

I think it’s a little bit of a blur. I mean, how much does anyone really remember their actual high school experience? I remember shooting almost every scene of that movie. I remember loving the dialogue. I remember how hard it hit me when I heard about Paul’s passing, because you always think that there’s going to be—this is the corniest thing I’ve ever said—but you always think that there’s going to be time to reminisce with people, the way I’m doing with you now—or the way I got to do with Matt[hew Lillard, who has a role in He’s All That]—about a time that was. 

I remember Matt was way more famous than I was at that point. We were all lightly surprised that he took the role. He was a little bit in his own head about being such a wacky, over-the-top, obnoxious character. He was a little bit horrified that he had to do a choreographed dance in front of everybody, which is pretty terrifying if you’re a nondancer. But his scene in She’s All That was just one of my absolute favorites. I was so grateful that he did [He’s All That] because frankly, I didn’t want to be the only one out with jazz hands going, “Hey, I’m back.”

Something that still resonates as a major teen-movie moment is you walking down the staircase in a red dress to “Kiss Me.” Did you have any idea filming this scene that it would become such a thing?

I remember thinking, really feels like I did great getting from the top step to bottom step. I got there. I didn’t really understand that they were trying to create such a gigantic cinematic quote, unquote moment. I’m glad that I didn’t, because I for sure would have been even more awkward than it probably was. Especially when they start shooting you in 48 frames, I do this dumb thing where you can’t help it, but you start acting in slow motion. It’s the most direct way possible to look like a total idiot.

There have been a lot of jokes and talk about Laney’s makeover from a “nerd” to “beautiful,” simply by removing her glasses and giving her a haircut. Is that an element of the movie that you see differently now?

I always thought of her appearance as being secondary when we shot the movie, that it was really more about her transformation of attitudes. She was so anti-everything—so ultimately standoffish and snobby in her own way. It’s really about our personal transformation. But that’s not what they make memes about, so here we are. I will say that the transformation of Tanner Buchanan in He’s All That, from a bird’s-eye view, is way more impressive than my makeover reveal.

Rewatching She’s All That and Josie and the Pussycats, I noticed how prophetic they are about influencer culture. The start of reality-star fame is shown in She’s All That, and the villain in Josie is literally an organization that subliminally influences young people to buy products through music. Now actual influencers like Kourtney Kardashian and Addison Rae are involved in He’s All That. Was that an evolution you thought about?

I deserve zero credit for taking these projects in a way that could seem strategic or prophetic. That would be a real misplaced compliment to myself. I had no idea. I loved the messaging in Josie, but I loved the humor even more and the character. I’m happy to be part of this movie because it’s important for me to update the messaging. I am a mom of two kids, and this is a much more socially, culturally responsible iteration of something that I was very directly part of putting out there. I will keep standing up and adjusting the narrative as needed, I hope.

You’ve spoken about the difficult time you had navigating the industry after Josie underperformed critically and at the box office. How did you emerge from that time?

I didn’t know that movie jail was a thing until I found myself in it. It is very real because show business is that—it’s a business. At a certain point it doesn’t matter if people think you’re talented or not. If you don’t make dollars and cents, you don’t get to go make dollars. That’s just the end. 

So how did I get out of it? I think that the fact that I didn’t care was most detrimental to my overall career and very helpful to my mental state simultaneously, because the independent scene was flourishing very much at that time. So I could just throw what was left of what could be considered my bankability into helping get other small movies made. That felt really good because I got to feel out my range and do parts that maybe I never would have gotten in huge-budget studio movies. Then I got to truly change the narrative and my position in the industry a great deal when I started producing and creating my own projects. That’s what I feel like was the biggest game changer for me.

She’s All That and Josie have only grown more popular. What do you attribute that to?

I didn’t know if the industry would have a place for me for much longer after I was not quote, unquote young anymore. So instead, to have what I feel to be a lot of love around me as time goes on, it feels wonderful, because the industry is really tempestuous and fickle still. It asks you to jump through all these hoops, and it’s not fun. So [the fact] that I can get support from people who have watched my work over the years feels tremendous. It’s kind of amazing how time, in that sense, has been really kind to me.

In recent years you’ve starred in a lot of romantic comedies, from Netflix to Hallmark. What drew you back into that genre?

Truthfully, I have always just had a deep love and respect for romantic comedies. I’m a person who wants it all. If you can have a movie with real dramatic stakes that’s also funny, that’s the movie I want to do. That’s why I’m in love with romantic comedy and dramedy as a genre. So what drew me back was just wanting to feel like I was home and that I was telling the kind of stories that I would want to hear. 

What’s funny is that I didn’t think that working for Hallmark was necessarily going to advance my career from an industry perspective, because it’s not...Look, CBS shows aren’t industry shows. Everyone says, “We gotta get you on a cool cable drama, this, that, and the other.” I didn’t think that it would help my career in a way that I could point to, but I knew that working for them was going to help me on a personal level—just making the kind of movies that I felt like making, that felt good to my soul as a person who’s a little bit too soft for this world sometimes. So the fact that—we’re going to sound real L.A. right now—the universe recognized that return to what is a real truth of mine and that it ultimately empowered and offered me so many opportunities from that, I think is a real lesson, for me anyway.

You’ve reinvented your career before. What does the next phase look like?

I would love to be a constant go-to presence in the romantic comedy genre. I believe with everything that I am that a rom-com is its own ecosystem. It can’t oversaturate. People like myself always want more of it. I also want to keep making my own things. There’s this constant feeling that the industry tries to give you of, “There’s a thousand people behind you waiting to take your spot, and when we hold up the hoop, you gotta jump through it.” So the idea that I can build my own [hoop] feels really, really good.

This interview has been edited for clarity and length.

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