What Rewatching Crossroads Reveals About Britney Spears

Movies don’t change as time passes, but we do. We watch them in the moment and then move on, leaving them behind as we see and learn new things. When we revisit a film made 20 years ago, we may think it looks dated, though that’s an imprecise and misguided term—it’s like blaming a movie for not having kept up with the times, an order that not even the greatest picture can fulfill. Movies remain innocently locked in the time of their making, which is part of what makes them such valuable cultural place-markers. But it can also, sometimes, make re-viewing painful.

In 2023, to rewatch Crossroads—the 2002 movie intended to be the movie breakout of Britney Spears, then an already massively successful pop-music star—is to revisit a time of casual innocence, of having no sense of a famous person beyond whatever charisma she might have as a performer. Crossroads hasn’t changed, but Britney Spears has. And today, to watch this sunny and open-hearted, if occasionally awkward, performer on a movie screen of any size is to be reminded of how little we ever really know about the inner lives of people whose job is to entertain us. (The movie returns to theaters on Oct. 23 and 25 for a special fan event to accompany the release of Spears' memoir, The Woman in Me.)

In Crossroads—directed by Tamra Davis, who’d made her name directing music videos, and written by Shonda Rhimes, not long before she hit it big with Grey’s Anatomy—Spears plays Lucy, a young woman who’s just graduating from high school in a small Georgia town, with the world opening wide to her. Her mechanic father (Dan Aykroyd) wants her to become a doctor; she’s smart and shy, the valedictorian of her class, and though she’s anxious to please her father, she’s not sure medical school is for her.

Read More: From Britney to Buffy, We're Suddenly Rethinking Postfeminist Pop Culture—and Nothing Could Be Healthier

As a kid, Lucy had two close friends, Kit and Mimi, though the bond between them has dissolved over the years. Kit (played by Zoe Saldaña) has become a cool girl, haughty and self-centered. Mimi (Taryn Manning), who lives in a trailer park, is five months pregnant, though she still harbors dreams of becoming a famous singer. The three have reconnected during a moment of post-graduation nostalgia—they've gotten together to exhume a special box they'd buried years earlier as kids, containing all their hopes for the future. Mimi, who has always dreamed of going to Los Angeles, announces that she's heading there to audition for a singing gig; a friend with a car, rock’n’roll guitarist Ben (Anson Mount), will be driving. Lucy and Kit try to talk Mimi out of her plan, only to end up deciding to tag along. Kit wants to surprise her fiancé, a student at UCLA. And Lucy wants to be dropped off in Tucson, where she hopes to reunite with the mother who abandoned her when she was three. (She’s played, with a veneer of blond-mom coolness, by Kim Cattrall.)

Crossroads is classic girl-friendship material, the kind of movie that, at the time, tended to do well with audiences (it was a box-office hit) but was often dismissed by critics (at least partly because stories about friendships between women were, then as now, often viewed as being somehow undeserving of serious consideration). When I reviewed the film upon its release, I had mixed feelings about it: I found it entertaining, if not particularly inspired, and though I thought Spears was a little tentative as a performer, I could also see there was a sweetness about her, something that went beyond acting skill, a spark of light that the camera picked up automatically. That’s part of the reason singers often make wonderful actors. That charisma, that desire to connect with an audience, is already radiating from their center—think of Cher, or Frank Sinatra. In Crossroads, Spears was nowhere in that company, but her cheerful magnetism translated to the big screen even so.

And especially given how rare solid, mainstream-movie craftsmanship has become, Crossroads looks even better today. Some of the story mechanics may be a bit creaky, but Davis and Rhimes were wholly willing to deal with the emotional complications of teenage pregnancy and rape—particularly the way men can be so casually clueless about acts of sexual violence that mean nothing to them but can change a woman’s life forever. Even so, it’s still Spears who really holds you. It's not necessarily that her performance seems better today, in any technical sense, than it did in 2002. But it’s impossible not to feel something for this young person attempting to work in a medium unfamiliar to her, relying on her innate charm and yet, it seems, somehow knowing it’s not enough to carry her through. Just as her character, Lucy, is uncertain about her place in the world, Spears seems unsure about how to communicate with a movie audience. We can almost see her second-guessing herself, as if she’s discovering for herself that playing a “real” girl, with real teenage problems, is much harder than bringing a song to life.

Read More: At Last, Britney Spears Gets a Voice in Her Future—and We Have Her Fans to Thank

At the time Spears made Crossroads, she was one of the biggest pop stars in the world, and also a controversial one: little girls, in particular, adored this onetime Mouseketeer, and parents everywhere worried that their daughters would be unduly influenced by her outfits and what they saw as the outré nature of her songs. To many of those parents, Spears’ professing her lack of innocence in “Oops!... I Did It Again,” or asking for one more hit of something in “Baby One More Time,” represented a danger to their daughters’ brain cells, or at least several steps back for feminism.

We now know that most of the women who grew up loving Britney Spears have turned out just fine. But we also know much more about how much Spears herself suffered as a person in the spotlight: We know all about her highly public 2007 breakdown, and about how, for more than 12 years, she was robbed of her autonomy both as a performer and as a human being, the prisoner of a conservatorship that kept her under her father’s control. The Spears of Crossroads, a young woman tentatively trying to master a new mode of performance, is a person who no longer exists except on a movie screen. There’s no way to go back in time and warn her how difficult her life would become.

Crossroads was Spears’ first and only movie. In a People Magazine excerpt from her upcoming memoir, to be released on Oct. 24, Spears reveals that making the film was extremely difficult for her. “My problem wasn’t with anyone involved in the production but with what acting did to my mind. I think I started Method acting—only I didn’t know how to break out of my character. I really became this other person. Some people do Method acting, but they’re usually aware of the fact that they’re doing it. But I didn’t have any separation at all.”

Spears is right about the dangers of Method acting: there are all sorts of techniques and modes of preparation an actor can use, some of them exploratory in a beneficial way and some of them deeply unhealthy, even risky. You can see how a young newcomer to movie acting, unsure of herself to begin with, might burrow so deeply into what she thinks is required of her that she loses sight of herself altogether.

But Spears’ performance in Crossroads is much better than she herself probably thinks it is—particularly in the moments where she’s doing what comes so easily to her, singing. In one of the movie’s central scenes, Lucy shows Ben a poem she’s written, one that expresses her sense of feeling excited by the life that awaits her even as she's stuck in the one she’s living now. The words “I’m not a girl, not yet a woman” spring from her notebook and into a song—written by Ben—that Lucy eventually sings. And in this moment, Spears comes off as fully relaxed and alive. She’s not “playing” a character, nor is she “becoming” one. For these few moments, she’s doing exactly what the greatest actors do: channeling the most truthful parts of themselves and spinning them out into the greater world. In so doing, she collapses the distance between her heart and ours. “This girl will always find her way,” she sings, as if she wholeheartedly believes it’s true, as if she’s giving her future self a piece of advice that somehow, presciently, she knows she’ll need. While singing in the moment, she's also singing for tomorrow. And just as a cat purrs to self-heal, she’s singing to herself as much as she’s singing to us.