Rachael Leigh Cook: ‘I was never at the top of the pretty-girl list’

The ‘She’s All That’ actor was one of the biggest teen stars of the late Nineties, but turned her back on romcom fame. As she returns in the gender-swapped remake ‘He’s All That’, she tells Adam White about dubious makeovers, revisiting her youth and feeling like a Hollywood outsider

Rachael Leigh Cook: ‘Weird was my happy place. If it was something strange, I wanted in on it’ (Photo: Tommy Flanagan / Makeup: Michael Shepherd / Hair: Ashanti Lation)

For 22 years, Rachael Leigh Cook has been haunted by a love song. Ever since Sixpence None the Richer’s tooth-achingly sweet “Kiss Me” soundtracked her transformation from bespectacled nerd to would-be prom queen in the teen classic She’s All That, the song has followed her everywhere. “It always comes on when I’m at the drugstore,” she says. “Because, let’s be real: it’s drugstore music. It’s not on anybody’s party mix or workout playlist. But what’s funny is that, even though I’ve heard it more times than many, I still don’t know what the heck they’re saying for probably three quarters of the song. I still don’t know what a ‘bearded barley’ is.” Stars, they’re just like us.

Cook is in the track’s immediate vicinity once again, because she’s in She’s All That’s quasi-remake, the gender-swapped He’s All That. In place of Freddie Prinze Jr is TikTok star Addison Rae in her acting debut, whose character takes part in a bet to turn a beanie-wearing outcast (Tanner Buchanan) into the most popular boy in school. It arrives on Netflix this week, theme song (sort of) intact. “Kiss Me” 2.0 is a little more dancified, building not to a twinkly crescendo but to an EDM drop. Like much of He’s All That, it’s a bit mortifying to anyone over the age of 20: a gentle reminder of the passing of time, its shifting cultural conventions and our collective lost youth. Cook plays the main character’s mum this time around, just to drive home the fact that we’re all 1,000 years old now. It must have been weird, surely?

“I think I would be spinning out about it a little if I wasn’t a mom in real life,” the 41-year-old says. She’s at home in LA’s San Fernando Valley, where she has carved out a lucrative producing career in recent years, alongside acting and raising two children – seven-year-old Charlotte and six-year-old Theo. “That would have been too bizarre, to be a person who didn’t have a child but then playing the mom of a young woman who is 20 in real life. I think that would smack me across the face pretty good.”

Cook, sitting in her office on Zoom in a white T-shirt and sporting sharp, rose-pink nails, is just as wide-eyed and coolly pragmatic as the roles that made her name. In the late Nineties, after stints as a child model and supporting player in kids’ movies, she found herself regularly cast as the deadpan, earthy and composed: the arty outsider in She’s All That; a garage-band rocker in the cult classic Josie and the Pussycats; the neat and unassuming secretary of The Baby-Sitters Club. If many of her teen movie peers at the time were marketed as figures of aspirational fantasy, Cook embodied a quiet, relatable poise.

“I never saw myself as shiny and pretty in the way that someone like Jessica Alba or Jennifer Love Hewitt were then,” she says. “They were the pretty girls and I thought of myself as far quirkier. If that was true, I do not know. But I was never at the top of the pretty-girl list.” She’s quick to clarify, though, that she is absolutely speaking in Nineties Hollywood terms. “I was not terrible-looking by any stretch! But there were so many stop-you-in-your-tracks beauties working at that time. I think I filled the role of ‘identifiable girl-next-door type’.”

Regardless, Cook’s entirely unsubtle beauty remains one of the silliest and most dubious elements of She’s All That. When we first meet her character, the unpopular Laney Boggs, her hair is unruly and she wears – the horror! – thick glasses. Only after she gets a trim and invests in some contact lenses is she made apparently palatable to the naked eye. She’s All That is inherently ludicrous, but Laney’s alleged grotesquery lifts the film out of romcom fantasy into the realms of science fiction.

I tell Cook that when I spoke last year to Ally Sheedy, who had her own iconic if vaguely problematic makeover in teen classic The Breakfast Club, she recalled fighting director John Hughes over how far it went. “I never liked the makeover,” Sheedy told me. “They wanted to take the ugly duckling and make her into a swan. As far as I was concerned, that wasn’t what I was doing with that character, but that was what they wanted.” Did Cook ever have her own misgivings about Laney’s transformation?

“I didn’t!” she says. “I’m aware that I may be overstating a very light, fluffy teen romcom here, or giving it too much importance, but I think it was just signalling a willingness to open yourself up. It’s a visual signal that you are open to being seen. Or being seen in a different way, as a new and vulnerable version of yourself.”

Before we go any further, though, Cook suddenly remembers that she and Sheedy go way back. “Ally Sheedy actually taught me how to drive!” she gasps. Wait, two of cinema’s coolest teen outsiders, both of them alleged eyesores given haircuts and pink ensembles for improvement, once shared a real-life formative experience? “She played my mom in a TV movie,” Cook remembers, of 1996’s Family Rescue. “We were in the parking lot of where we were filming and she asked if I had my learner’s permit yet. I said no, that I hadn’t even started and she just said, ‘Get in the front seat, we’re gonna do this!’ It was fantastic.”

Cook and Freddie Prinze Jr in the original ‘She’s All That' (Miramax/Kobal/Shutterstock)

It’s a wacky coincidence, but speaks to Cook’s unique spot in Hollywood teen movie history. Kevin Bacon may own the Six Degrees of Separation game – the belief that he can be linked with every actor imaginable in six film projects or less – but Cook is at least the star of its teen-movie equivalent. By the early Noughties, Cook had guest-starred on Dawson’s Creek, had on-screen romances with almost every Seventeen Magazine pin-up of the era (among them James Van Der Beek, Josh Hartnett, Ryan Phillippe and Jonathan Taylor Thomas), and played off of practically every actor synonymous with the era’s “youthquake” of high school-centric film, from Seth Green and Clea DuVall to Kirsten Dunst and Gabrielle Union. Throw in Sheedy and she’s at least made inroads to the Eighties, too. Did it feel like one big community back then?

“Maybe I just wasn’t invited,” says Cook, a touch forlornly, “but most of us didn’t run in the same social circles by any stretch. But I do consider people from that time as sort of my substitute for not really having high school friends, because I started working when I was so young.”

Amid a cast of teenagers who weren’t alive when She’s All That was first released, Cook found a friend in Matthew Lillard on the set of He’s All That. The Scream actor – who played Prinze Jr’s love rival in the original film – is the school principal in the remake (Prinze Jr does not feature this time). “I realised that I didn’t really know him even though I thought I did,” she says. “You don’t know anything about this person, even though you’ve shared something that’s such a touchstone in your lives.”

Cook and Addison Rae in Netflix’s ‘He’s All That' (Kevin Estrada/Netflix)

He’s All That marks Cook’s second collaboration with Netflix in two years, following on from 2020’s romantic comedy Love, Guaranteed, which she also produced. If it feels like a bit of a mainstream comeback, with Cook seeming to have dropped off the radar in the wake of Josie and the Pussycats, you’re partly correct. Back then, she says, she didn’t want to be a big romcom star. Instead, she idolised Parker Posey, the queen of independent film at the time, and Cook’s scene-stealing co-star in Josie.

“She was just the most potently cool human I had ever met or seen on screen, so I sought to be as awesome as Parker Posey, only with, you know, non-impressive results,” she laughs. Whether it was the right or wrong thing to do in terms of fame, she gravitated towards the gnarlier and stranger. “For a while I was banging out probably four movies a year,” she remembers. “I was feeling really creatively fulfilled. I was cast as a schizophrenic a couple of times, and a rape victim I think another three or four times. So I was doing things that felt challenging and that required me to dig deeper. Weird was my happy place. If it was something strange, I wanted in on it. The actual results of all of that? I have no idea. But I had a great time.”

Those darker impulses shifted, though. She’s now very happy embodying the romcom-regular role she spent her early twenties rejecting, and is the star of a franchise of romcoms for the US channel Hallmark, with titles like Autumn in the Vineyard and Valentine in the Vineyard. “The head space I happen to be in now is that I’m a lot more drawn to feel-good content,” she says. “It feels good to dream a little.”

And if that means staying most famous for a film she made 22 years ago, one that seems to follow her from supermarket to service station and every drugstore in between, so be it.

‘He’s All That’ is released on Netflix on Friday 27 August