When I saw Crossroads in theatres, I expected a shallow hate-watch. What I found instead surprised me

Anne-iversaries is a monthly column by writer Anne T. Donahue that explores and celebrates the pop culture that defined the '90s and 2000s and the way it affects us now (with, of course, a few personal anecdotes along the way).

Twenty years ago, I stood by an explanation: I was seeing Crossroads as a joke. Yes, one of the friends I was going with was a Britney Spears superfan and the other was genuinely interested in the premise, but I insisted I was the exception.

I was better than our generation's biggest pop star and her cinematic debut. I was too smart to invest real thought into a movie about a teen girl making her way across America to meet the mother who didn't love her. I was a teen girl who wouldn't be caught dead listening to Britney, let alone watching her for almost two hours. (And unlike Britney, I'd rather die than wear a bucket hat.)

In 2002, it wasn't hard to write off Crossroads if you resented Spears for being what you were not. Where Britney seemed confident, self-assured, and oozing with sex appeal, I was insecure, needy, loud, and peppered all flirtations with quotes from Teen Girl Squad. I dismissed Britney's foray into cinema with an eye roll I hoped would hide how inept I'd started to feel.

The critical conversation around Crossroads made this easy. Leading up to its release, it had been branded as the second coming of Glitter (Mariah Carey's failed attempt at movie stardom the previous year) and considered trash for anyone who took art, culture, or their own time seriously. Hating Crossroads was the way things were supposed to be.

But the haters were wrong. Written by Shonda Rhimes (yes, the Shonda Rhimes), the movie never plays like an excuse for Britney to simply snag some screen time. In fact, it's shockingly heavy. The story tackles serious subject matter that necessitated actors who could carry it (or at least not let it drop), and while Spears never seemed like the next big Oscar contender à la Gaga, her ability to keep her head above water while selling this narrative deserves respect. Especially when looking back two decades later and realizing that behind the scenes, her whole world was beginning to fracture.

Rooted in the story of Lucy (Spears), a girl raised by a single father (Dan Aykroyd), Crossroads takes viewers along for the triumphs and tragedies that accompany three estranged childhood friends who reunite for a road trip to L.A. Lucy aims to meet her birth mom (Kim Cattrall), while childhood pals Kit (Zoe Saldana) and Mimi (Taryn Manning) see the west coast as the starting point to the rest of their lives.

For the most part, the movie is silly and weird, with scenes that include the girls performing karaoke for tips in New Orleans and/or belting out Sheryl Crow to the chagrin of their driver, Ben (Anson Mount), with whom Lucy ends up falling in love. But then things get dark.

As the girls re-learn to trust each other, Mimi admits that the baby she's carrying is the result of a sexual assault. Kit opens up about her fractured relationship with her mother, whose warped views on body image have left her with an understandable neurosis. Lucy grapples with the revelation that the person she believed her mother to be is far from who she really is. And this is all before Mimi loses her baby and Kit learns that her own boyfriend is Mimi's offender.

My friends and I sat silent in the theatre, breaking from our marathon of jokes and running commentary to grapple with what we were seeing. For a road trip movie to evolve into an unpacking of profound trauma was unexpected and jarring. Crossroads was touted as a movie connected with the chart-topping "I'm Not a Girl, Not Yet a Woman" and a glorious cover of "I Love Rock 'N Roll." Revealing to friends at school that I intended to see it was met with laughter, usually spurred on by me. A story about betrayal, violence, and emotional abuse wasn't what TV commercials or trailers suggested. As alluded to by reviews (and the dismissal of most people), Crossroads was supposed to be an empty teen girl film for empty teen girls. There wasn't supposed to be anything real.

But this was a movie directed by Tamra Davis and written by Shonda Rhimes. Of course it wasn't ever going to just be a simple tale of what happens when three friends hop in a classic car with a handsome man. Not just because Rhimes went on to build her own empire by telling uncomfortable and thought-provoking stories, but because movies targeted to teens are usually not as embarrassing or shallow as they're made out to be.

Did this make Crossroads good? Full disclosure: it was just fine. But what makes it worth talking about now is the way it helped establish the way we tell teen stories today — stories that seem frivolous at first glance, but turn out to dive into the bleak realities of being a young person. Crossroads forced suburban teens like myself circa 2002 to acknowledge that every existence is unique in its beauty and horror. It may have blindsided us with its third act, but it planted the seed for a life lesson: you don't know until you know. Being a person is never clear-cut or easy. Instead, we are defined by our complexities and complications, by our victories and by our darkest moments.

This is something many of us have come to understand about Britney Spears more recently. Her own words and documentaries like last year's Framing Britney Spears have finally shed a light on the way she'd been built up as the world's biggest pop star, only to be completely powerless behind the scenes. Finally, Britney Spears the Brand™ was being perceived as a human being — one who was vying for control over the building blocks of her own adult life. Not unlike her character Lucy, Britney herself was seeking much-needed independence, working to tell her own story, and driving into the future with only the promise of truth.

Crossroads was by no means a critical success, but according to the $61 million it recouped at the box office, it did draw audiences of viewers who obviously appreciated it. And here's the thing: there's a lot to appreciate.

As Lucy learns, growing up is terrible. And even worse is the revelation that moving on from one's teen years into young adulthood tends to bring with it a significant sense of sadness and grief. As a teen, I looked to the adults who shut down a movie they likely just didn't want to see, and I looked to peers who, like myself, used irony as a form of armour meant to deflect vulnerability. I didn't want to open myself to being authentic and sincere via a movie set to a soundtrack by Britney Spears. I wanted to laugh at her, and it, and us.

Crossroads may not have seemed like it was going to give me a lot to think about. But sitting at a Crabby Joe's table and dissecting the movie afterwards, I realized I didn't have much to make fun of. If I was really being honest with myself, I even kind of wanted a bucket hat.