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Where The 'Crossroads' Characters Def Ended Up 20 Years Later

It’s a huge week for the Britney Spears community. Not only does her $15M memoir drop on October 24, movie theaters are celebrating the launch with a rerelease of Britney’s 2002 road trip movie Crossroads

In its day, Crossroads was universally panned by critics, with a 15% score on the Tomatometer. I get that it’s not prestige cinema, but for reference, the new Paw Patrol movie is currently sitting at 77%, and people HATE Paw Patrol. You can’t seriously tell us that Britney’s trite but endearing coming-of-age movie is 62% worse than two hours of grating giggles from the world’s least favorite animated police dogs. 

To add insult to injury, Britney herself was awarded the Razzie for Worst Actress (excuse you?) and the iconic movie song “I’m Not A Girl, Not Yet A Woman” won Worst Song, when we all know it’s a certified bop.  

Anyway, since the film concludes with its heroes Lucy, Kit, and Mimi burying a “wish box” of their hopes and dreams for the future, where do you think they’d be now, 21 years later? Here’s my predictions for how the those crazy teens navigated the rest of the 2000s: 

Lucy Wagner

Image Credit: Summit Entertainment

How many 18-year-olds do you know that have as much grace and class as Lucy? 

Since she was valedictorian, my gut tells me she isn’t dropping everything to pursue a pop career after winning that LA singing contest. “I’m Not A Girl” slaps, but it’s no “…Baby One More Time,” and Lucy is a realist! 

She’s gonna go to a respectable college like UCLA and end up pursuing a master’s in psychology, jumpstarting her fulfilling career doing music therapy or something noble like that. 

She’ll also bag a rich husb, because let’s not forget she looks how she looks, so the income restrictions of her righteous career path won’t pose a problem to the lifestyle she deserves. 


Image Credit: Summit Entertainment

Kit walked so Gretchen Weiners could run, giving us the original “I can’t help it if I’m popular” zinger when she faux-laments that every girl in school is jealous of her. 

Creating an aura of aspiration is exactly what an influencer needs to thrive, and given her history with fat camp, I see Kit becoming a body positivity wellness influencer. 

But we all know the type: She’s a double zero who posts pictures of herself eating pizza in a bikini (women should be able to eat pizza!!!) and humblebrags about how frustrating it is to never be able to find her size in stores, all under the guise of promoting a social movement that she only associates herself with for sponsorships and clout. 


Image Credit: Summit Entertainment

Mimi always wanted to escape her hometown trailer park and live her fantasy life in California, so after the road trip ends, I see her getting cast on MTV’s The Real World: San Diego

She was crazy enough to drive to Los Angeles with a guy she barely knew, so she should have no problem living in a house with a bunch of rando degenerates. 

Plus, she knows how to throw a punch, and could bring some major Farrah Abraham energy to set that could elevate her to a reality TV mainstay — I’m talking The Challenge regular, an Are You The One? stint where she meets her on-and-off fiancè, a TMZ blast about a DUI — you know, the American Dream. 

Ben Kimble

Image Credit: Summit Entertainment

Ben is a himbo! He and Lucy probably make a run at long-distance dating for a bit, but she eventually outgrows him and breaks things off in the nicest way possible. 

He’s heartbroken for a few months, until he meets Emily at the supermarket. They were both reaching for the same box of pepperoni Hot Pockets! They get married, and he goes on to be a hardcore wife guy. 


Image Credit: Summit Entertainment

Since he essentially made a PowerPoint presentation about why he and Lucy should lose their virginity together (the most compelling reason being that they were lab partners for three years), Henry would do well to take those skills to an ad agency. 

It’s basically the same thing! Putting a bunch of idiotic ideas on fancy slides with industry buzzwords, and hoping your client is dumb enough to buy it. 


Image Credit: Summit Entertainment

On a rewatch, Lucy’s long-lost mother Caroline is honestly kind of iconically cold (helped by the fact that she’s played by Kim Cattrall). 

Imagine the daughter that you abandoned comes all the way to your ugly ass beige house in Tucson to finally meet you and instead of feigning any niceties you’re just like, “I have to pick up my real child from swim practice, don’t let the door hit you on the way out.” 

Caroline definitely went on to become one of the convicted parents in Operation Varsity Blues when she bribed the Duke soccer coach to help admit her pasty son who bombed the SAT, but she didn’t get any media attention during the scandal because she wasn’t famous, which honestly made her a little jealous of Felicity Huffman. 

Emma Sharpe
Emma Sharpe
Emma Sharpe is a New York based writer and marketer. She's a Kardashian apologist and finds a Survivor metaphor for every life situation. You can find more of her pop culture ramblings at