Rachael Leigh Cook Was Always Worth the Bet

Rachael Leigh Cook is having a full-circle moment. Twenty-two years after she descended a staircase in a little red dress to the beat of Sixpence None the Richer, the “She’s All That” actress finds herself once again in a teen makeover movie.

This time, she’s on the fringe as the mother of an influencer (played by Addison Rae) in “He’s All That,” Netflix’s gender-flipped remake of the 1999 hit that starred Cook and Freddie Prinze Jr. And this time it’s a quirky boy who sputters a version of Cook’s classic line, “Am I a bet?”

Now 41, Cook was initially skeptical about joining the new film, fretting, “What if my role is trotted out to signal to everyone who might have been a fan of the first movie, ‘She said it’s OK! She’s still alive, isn’t that fun?’”

But Cook isn’t just alive. She’s thriving. And her small part in “He’s All That” is only one marker in a decades-long career that includes star turns in some of millennial audiences’ most cherished films and a permanent place in the pop-culture zeitgeist of the ’90s and early 2000s. Now, she’s ready for a new era.

Cook, as you might expect from the relatable roles she’s known for, has a knack for making strangers feel like she’s their best friend. Wearing an oversized T-shirt and perched on a rattan chair at her brother’s house in Los Angeles, she peppered our recent video interview with a stream of her own inquiries about everything from my cat to my parents to my love life. The same expressive eyebrows a director once instructed her to control by taping them down now alternately furrowed with concern and leapt with delight.

“All of that is completely genuine,” her friend and co-star from “The Baby-Sitters Club,” Marla Sokoloff, said in a separate call. “She’s exactly who you want her to be. Multiple times, she’s forwarded me a meeting that she’s gotten for herself and been like, ‘I don’t think this is for me. You need to play this part.’ Who does that? She doesn’t have a bad bone in her body.”

Rae — who was born the year after “She’s All That” was released and rose to prominence on TikTok — is navigating a different Hollywood landscape than the one Cook entered as a teenager in 1995, an era before social media or #MeToo. The younger star spoke about Cook, as well as ’90s trends like low-rise jeans and claw clips, with an earnest reverence.

“Rachael is so inspiring. You can tell her heart is very pure,” Rae said. “She knows more than a lot of people how hard this industry can be, and she made it very clear to me that it’s a lot of work.” (Cook noted that she refrained from giving too much career advice to Rae at the risk of sounding like “some busybody old lady.”)

The daughter of a social worker and an artisan weaver, Cook started off modeling for Milk-Bone boxes and Target print ads in Minneapolis before booking her first audition in Los Angeles at age 15 and winning the part: Mary-Anne in the 1995 movie adaptation of “The Baby-Sitters Club.” Months later, another literary role followed as Becky Thatcher in Disney’s “Tom and Huck.”

On the set of that film, Cook found herself next to two actors at the height of child stardom: Jonathan Taylor Thomas, whom she overheard say things like, “It’s difficult to be a Democrat in my tax bracket” at age 13, and Brad Renfro, who, she recalled, secured his role by wielding an actual hatchet and chasing the casting director around the audition room.

“It was a very up-close and super vivid example of different ways that you can exist in Hollywood,” Cook said. “I think, at least in my 20s, I lived somewhere straight in the middle of that.”

Gifted with a wry sense of humor and an often underutilized comedic timing, Cook hoped, above all, for a career like that of Parker Posey, with whom she co-starred in “The House of Yes” and “Josie and the Pussycats.” But without TikTok or Instagram (platforms on which Rae has a combined 120-million-plus followers), Cook’s public persona was at the mercy of Seventeen and Angelfire fansites, which determined how to present her to their readers.

In early interviews, she was often likened to fellow Minnesotan Winona Ryder: both had delicate features and cool-girl clout. Matthew Lillard, Cook’s co-star in “She’s All That” and the remake, saw her as yet a different type of leading lady.

“I remember thinking to myself, ‘She can be the next Julia Roberts,’” Lillard said in a phone interview. “She had that shine in her eyes and the sparkle about her personality. She’s wicked smart. But at the same time, she doesn’t believe the hype. She’s the exception to the Hollywood rule.”

Further breaking the mold, one of Cook’s most impactful roles came not from a movie but from a public service announcement: she smashed eggs and aggressively destroyed an entire kitchen to demonstrate the effects of heroin addiction. That 1997 “This is your brain on drugs” spot, she said, “ended up moving the needle for me in terms of getting slightly edgier roles.” Twenty years later, she filmed a similar ad, highlighting how the war on drugs disproportionately affects people of color. The update, Cook said, “needed to happen knowing what we know now.”

While Cook’s anti-heroin ad proved exceedingly popular, “heroin chic” was also the dominant ’90s beauty ideal, glorifying ultrathin body types and popularizing an often unhealthy standard for models and actresses — and the ordinary teenagers who were bombarded with those images onscreen and in magazines.

Over the course of her career, multiple directors asked the petite star to lose weight days before filming. One of them, Cook said, was Peter Howitt, the director of the 2001 film “Antitrust,” who cushioned the insinuation that she’d overindulged at Thanksgiving with the addendum that he’d told her male co-star, Ryan Phillippe, the same thing.

“I just immediately burst into tears. And he felt terrible and immediately took it back,” she said. “But it doesn’t mean I wasn’t offended. It doesn’t mean I don’t remember it.”

A representative for Howitt wrote in an email that the director was instructed by the film’s producers to speak to the actors, noting that Howitt “regretted being used as a messenger,” apologized, and has never “personally had any issue with the physicality of any actors.”

“She’s All That” and “He’s All That” are both Miramax productions, though only the former had Harvey Weinstein’s involvement. While the producer, who is currently serving a 23-year prison sentence for rape and sexual assault, wasn’t a fixture on the set of the 1999 film, Cook did encounter him over the years. (She also starred in the Miramax films “All I Wanna Do,” “The House of Yes” and “Blow Dry.”) Cook believes her manager accompanied the then-oblivious young star to those work meetings to protect her, but she also instructed her client to send Weinstein “get well” cards when he was in the hospital.

“I think that I overheard enough people calling me mature that I believed it myself. But that wasn’t actually true,” Cook said. “In retrospect, was I equipped to navigate the industry? Zero percent.”

After “Josie and the Pussycats,” a campy, female-centric adaptation that’s now widely appreciated, bombed at the 2001 box office, Cook decided to focus on independent films, both because she needed to get out of “movie jail” and because of her desire to be part of that offbeat, flourishing scene.

“I really thought what everyone told me was correct when they said, ‘What we need to do now is make sure you’re taken seriously,’” she said. “I definitely did things for the wrong reasons.”

Pre-“Josie,” she had turned down the part of Rogue in the “X-Men” franchise in order to shoot multiple smaller films and avoid acting on a green screen. The superhero role went to her “She’s All That” co-star Anna Paquin instead. Cook is reluctant to draw more attention to her “huge misstep,” noting, “As soon as I saw the posters for it, I knew that I’d made a mistake.”

Cook currently finds herself in a transitory state, on the cusp of a new chapter. Her 15-year marriage to “The Vampire Diaries” actor Daniel Gillies, with whom she shares two children, 7-year-old Charlotte and 6-year-old Theo, ended in divorce. The actress Judy Greer, her friend, subsequently set her up with the producer Kevin Mann.

“I recommend divorce highly,” Cook said. “I’m sorry, I know I sound like a quitter. But I believe it wholeheartedly. Life is too short not to be true to who you are and what you need.”

In recent years, she’s pivoted to feel-good fare, starring in a string of Hallmark movies tied to various seasons and holidays, as well as the 2020 Netflix rom-com “Love, Guaranteed,” which she also produced. While she’s a fan of the comforting genre, there’s still so much more she’d like to explore. Dark comedies. Posey terrain. “Things that are earnest but still strange and a little bit bent,” she explained.

As Lillard put it, “Rachael Leigh Cook is someone to be reckoned with. I’m super excited for the world to remember that.”

She’s also slated to star in and produce Netflix’s coming romance “A Tourist’s Guide to Love,” based on her own story idea. Producing has served as one way to get back the control her early career lacked.

“I’m a lifer. I’ve been around the block,” Cook said. “It used to be so not OK for a woman to even get older. Now, I’m older and somehow it’s OK. It used to be, you’re never going to really have any power if you’re not a man. Now, the women I know are running everything.”