40 Thoughts We Had While Rewatching Britney Spears’s ‘Crossroads’

It is not an exaggeration to say that I’ve been waiting for the Shonda Rhimes–penned(!) 2002 film Crossroads to hit Netflix for pretty much the last five years, and now finally my wish has been granted. I knew instantly that I needed to revisit this classic, but I also reached out for help from Vogue’s senior fashion and style writer, Christian Allaire, arguably the biggest Britney stan on staff, knowing that two devoted rom-com heads are better than one. Below, read all the thoughts we had while rewatching Crossroads.

1. Christian Allaire: Our first Britney spotting is her as Lucy, singing Madonna’s “Open Your Heart” in her room. I love the princess of pop’s nod to the queen of pop. Side note: Have you ever heard Britney’s cover of “Burning Up”? Underrated bop.
2. Emma Specter: I never had until this moment, but I’m playing it on YouTube now, and it is everything I never knew I needed.
3. CA: Lucy is being painted as a nerdy valedictorian. It is hard to imagine Britney that way—she’s way too much of an It girl for this—but let’s go along with it.
4. ES: I refuse to live in a world where Britney Spears is not popular, sorry.
5. CA: Lucy’s graduation dress is so cute. An embroidered pink number. Very Miu Miu.
6. ES: I just looked up the costumer, and it’s Barbara Siebert, who did the clothes for a bunch of iconic ’90s films, including Die Hard and Some Kind of Wonderful.
7. CA: Kit (Zoe Saldaña) is, for some reason, engaged to some UCLA dude. Girl, you’re too young to be getting married! Have fun! Date! Sleep around!
8. ES: Wholeheartedly agree. Also hear me out: There’s something a little bit queer about Kit’s early engagement to a UCLA bro, but don’t ask me to explain further.
9. CA: Justin Long is trying to lose his virginity to Lucy, who is not having it. There are no sparks between these two lab partners. But aesthetically they are a hot couple.
10. ES: Who knew Justin Long had abs???
11. CA: Taryn Manning’s character, Mimi, is definitely the edgy girl I’d be friends with in high school. I’d definitely skip class and sneak a cig with her. (Just kidding, smoking is bad.)
12. ES: I’d be right there with you and Mimi, pretending to smoke confidently (then hacking up a lung).
13. CA: Okay, things have escalated. Estranged friends Lucy, Kit, and Mimi have all decided they are taking a road trip to California together. Mimi, who is pregnant, wants to audition for a record company; Lucy wants to find her mom; Kit wants to visit her fiancé.
14. ES: I love the idea that three girls who never hung out in high school would celebrate graduation by immediately traveling cross-country together.
15. CA: Lucy’s double denim and bucket hat is sooo Y2K. I’m here for it.
16. ES: Did Crossroads plant the seeds for the bucket-hat revival?
17. CA: The fact that RCA snuck in ’NSync’s “Bye Bye Bye” into this soundtrack when Britney and Justin Timberlake were dating at the time…you gotta love a Hollywood publicity team.
18. ES: Ugh. All Britney did was advocate for Justin, and all he did was screw her over! (Sorry, I’m still mad.)
19. CA: The three girls are convinced their driver, Ben (Anson Mount), a friend of Mimi’s, might be a serial killer. Yet…they still get in the car with him?? Make it make sense.
20. ES: I am officially old enough to relate more to these girls’ mothers than to them (cool realization), and I’m very stressed.
21. CA: Ah, yes, we have arrived at the classic road-trip-movie trope—when the car breaks down. It causes everyone to have a big fight. It’s not that serious, babes. Call a tow truck!
22. ES: This is something I have learned firsthand on my own road trips with besties: Your fellow drivers are not the enemy. The car is the enemy.
23. CA: Kit’s butterfly pants are so hot. Love her chain belt too.
24. ES: Do I need a chain belt?
25. CA: Now they’re doing karaoke to raise money for the broken car part. I love that this is their first idea—because performing for strangers is a famously fruitful venture.
26. ES: If you could make money doing karaoke, I wouldn’t have any credit-card debt. (Yes, I am good at karaoke and bad with money.)
27. CA: These saucy punk-rock karaoke outfits, though. Lucy’s crimped hair! I live.
28. ES: Soooo Lizzie McGuire coded.
29. CA: Turns out Lucy is a total star on stage while singing “I Love Rock ’n’ Roll.” She works the pole, just like Britney does in her “Gimme More” video. Somehow the karaoke gig makes them rich, and they’re suddenly staying at, like, The Ritz. They order all the room service. How much money did they make performing one song?
30. ES: I love scenes in movies where broke women get a shot at opulence and go all in on room service. (See also: Kate Bosworth eating blueberry pancakes in her robe in Blue Crush.)
31. CA: They’re almost to California. Lucy shares a poem with that hot serial-killer dude who, it turns out, isn’t a serial killer. The poem is lyrics to her wonderful ballad, “I’m Not a Girl, Not Yet a Woman.” He composes music on a piano to go with her lyrics. He sure has rizz.
32. ES: Rizz, indeed. This actor creeps me out, though, I don’t know why.
33. CA: Lucy finally gets to meet her estranged mother, who is played by none other than Kim Cattrall. How fabulous. She’s a chic Tuscan housewife who wants nothing to do with her. So we hate her, obviously. (Her house is great, though.)
34. ES: Kim Cattrall, they could never make me hate you!
35. CA: Things took a really dark turn. Mimi loses her baby, and we find out that Kit’s fiancé was the one who got her pregnant, against her will. But somehow, through the tough times, it brings the three friends closer.
36. ES: Yeah, this shit is rough, and I honestly kind of forgot about it.
37. CA: They finally make it to California. Lucy and the killer-but-not-a-killer guy get it on. It’s also suddenly decided that Lucy should audition for the record company—not Mimi—despite this whole idea being Mimi’s dream. But sure, we stan Lucy—let’s get her discovered!
38. ES: If I were Mimi, I’d be pissed.
39. CA: Lucy sings “I’m Not a Girl, Not Yet a Woman” and totally wows the crowd. She performs in a crop top with billowy sleeves and low-rise jeans. She looks like a pop star. I’d sign her. We never know if she did land that deal—but we’re gonna go ahead and say yes.
40. ES: I mean, obvi, right? She’s Britney!