1. Legally Blonde
In many ways Legally Blonde is the quintessential film for the Millennium Girl. It has all of the trademarks of the Decade of Spice — ample girl power, Lisa Loeb on the soundtrack, brightly colored wardrobes — while leaving behind that phase where people still thought Dave Matthews was good. I’m glad that national nightmare is over. Legally Blonde was perfectly groomed in the tradition of smart-dumb comedies like Romy and Michelle’s High School Reunion and Clueless, whose effervescent ditziness masked whip-smart scripts and surprisingly good messages for young women. (Summary: Don’t hate on other women, you’re more than your credit card and you don’t need to get married at 16, especially not to your brother.)
Legally Blonde was a BFD to girls of a certain generation, who learned that you don’t have to bend and snap to get into Harvard. You can get in with hard work and Luke Wilson as your lusty sidekick. And they said you couldn’t have it all.
Honorable Mention: Spice World, which came out a little early for this list, but always merits inclusion anyway.
2. 10 Things I Hate About You
Released the same weekend as that little film called The Matrix, 10 Things I Hate About You got buried under that Wachowskis hype, generic marketing and a general malaise with teen films. None of its stars were big enough to be draws on their own yet, despite the fact that it introduced a lot of us to Heath Ledger and a newly adorable Joseph Gordon-Levitt, who was finally shedding the baby fat.
However, 10 Things became a teen cult classic (that even got a spinoff TV show) because it’s both sharp and wise about teenage girls, while gently mocking them. (That black Sarah Lawrence acceptance letter is genius.) While throwing in references to Betty Friedan, The Raincoats and Shakespeare for the smart girls, it’s also a touching film about sibling rivalry and a family dealing with its daughters’ coming of age. It’s a movie you grew older with, one that seemed smarter and truer with each passing year. What can we say? That Shakespeare knows his stuff.
Honorable Mention: Save the Last Dance, because a) it’s both much better than anyone would have expected b) filmed in Chicago and c) has Kerry Washington in it. I worship the ground that woman walks on.
Heartbreakers pulled a clever bait-and-switch with its target audience. The marketing promised lots of Jennifer Love Hewitt doing whatever it is that she does, and the teens showed up because a) she was so hot then and b) they wanted to find out exactly what she does. However, Jenny Love plays a supporting role in the film, and her screen time is next to inconsequential. That romance with Jason Lee is so cardboard that I didn’t remember he was in the film until I looked it up on IMDB.
Instead, director David Mirkin gave them a smart screwball crime comedy — in the tradition of Dirty Rotten Scoundrels and Ruthless People. Mirkin was the showrunner of The Simpsons in its heyday and Heartbreakers retains a lot of its snappy energy, assisted with a razor sharp script by the Liar Liar team and wily performances from Gene Hackman and Sigourney Weaver, whose timing has rarely been better. The teens came for Hewitt, but they stayed for Sigourney.
Honorable Mention: Can’t Hardly Wait, which proves Lauren Ambrose is much better at everything than Jennifer Love Hewitt. I still don’t get why Ethan Embry wasn’t into her instead.
4. She’s All That
If you weren’t aware of She’s All That in 1999, you must have been headless or in a Carrie White situation, where your fundamentalist mother forbid you from knowing the ways of Freddie Prinze Jr.’s secular flesh. She’s All That was an inescapable phenomenon, the movie that taught us high school students are phenomenal dancers and all girls just want to be Julia Roberts in Pretty Woman, except for that whole hooker thing.
Honorable Mention: Jawbreaker, which is basically Heathers Redux. It also proves that Rose McGowan is as great as we all think she is.
5. Cruel Intentions
I don’t know who thought that Claderos De Laclos’ most sinful novel needed Sarah Michelle Gellar in it, but that person is a genius. Cruel Intentions isn’t as high-minded as the Stephen Frears version, but it was a deliciously campy and vampy take on Les Liaisons Dangereuses, one you could sink your kitschy teeth into. Gellar is over-the-top perfection as Kathryn Merteuil, the forbidden desire of Ryan Phillippe’s Sebastian, the Patrick Bateman of the prep school set. Everything in the film is delightfull tongue-in-cheek, especially Selma Blair’s brazen airhead, who gave us one of 1999’s most quotable lines in “Secret society! Secret society!”
Between this, Election, Man in the Moon, Legally Blonde and the aforementioned American Psycho, this truly was the best of all times for Reese Witherspoon. Where you been, gurl?
To Reiterate: You need to see Election, if you haven’t already. I feel like I am Tracy Flick. But nicer.
6. Bring It On
Bring It On is one of those movies that has stood the test of time — from being adapted into a Broadway musical to a pseudo-remake in Pitch Perfect, the heir to Bring It On’s cheertatorship. Although the film got a lot of attention for its racy script (which somehow snuck in with a PG-13?), the movie succeeds because of its infectious energy, memorable characters and cheer routines that still impress a decade later. The final showdown is still genuinely thrilling, even if you’ve seen it a million times, just to see the seamlessness of its choreography. That movie could make even the hardest cynic into a cheer fan. How can you resist?
Honorable Mention: Moulin Rouge, which turned the jukebox musical into a glorious acid trip.
7. Girl, Interrupted
Girl, Interrupted brought Sylvia Plath to a lot of people who were still too young to know what The Bell Jar was. James Mangold’s adaptation of the Susana Kaysen memoir plays at Plath crossed with One Flew Over the Cuckoo’s Nest, giving the “women in asylum” narrative some much-needed vigor and zest. Although the movie gained notoriety for the rawness of Angelina Jolie’s Oscar-winning performance (as she acted the walls off that mental hospital), what always strikes me anew about the film is how brazenly funny it is. Like The Craft, you find solace and camaraderie in spending time with these outcasts, whose struggles in many ways mirror your own.
And if nothing else, Girl, Interrupted taught you what a rim job was. Still can’t believe my parents let me watch it.
8. Miss Congeniality
As an avowed non-fan of Sandra Bullock (who wants me to love her for always doing the same thing), Miss Congeniality is one of the two-ish Bullock vehicles I have a soft spot for. Although it looks like a paean to beauty conformity, Miss Congeniality was a love letter to the girls who don’t fit in. Sure, they do the stock makeover subplot where you find out she was HOT ALL ALONG, but Bullock goes back to being her quirky self at the end, just with slightly better clothes. (Note: This is almost the exact same outcome as The Devil Wears Prada, which I think makes Michael Caine the film’s Miranda Priestly.)
Honorable Mention: Drop Dead Gorgeous, which nails small town Midwest life so well it makes me uncomfortable. Also, it’s one-liners are to die for (“She’s skinny, Amber, not deaf!”).
9. Never Been Kissed
As the “biggest loser” in middle school, I related to this movie in painful, uncomfortable ways. I felt like I was Josie Grossie, and I could grow up, move to Chicago, go to Northwestern and become a writer. (Oddly, most of these things actually happened.) This movie was hope that good things happen for you after your K-12 years finally ceased, and you could come back a completely normal person. You didn’t have to be Josie Grossie anymore, but you’ll never leave her behind. She’s a part of you.
Honorable Mention: Ever After, in which Drew Barrymore makes a surprisingly charming Cinderella.
10. Bridget Jones’s Diary
Bridget Jones is my spirit animal. I feel like I get her in ways I’m not supposed to understand movie characters, a bond strengthened by drinking, overeating and being terrible at karaoke and public speaking. I got into Bridget Jones in high school, although I originally watched it when it came out, and I loved it both for its wit and its insistence that I could be loved just the way I was. Also, for any fans of the BBC Pride and Prejudice miniseries, the film and book’s overt borrowing from the Austen canon (including the casting of the effortlessly yummy Colin Firth) was a waking wet dream.
America might have discovered the charms of Mr. Firth later (circa Love Actually and The King’s Speech), but Bridget Jones fans knew what was up. We got there first.
Honorable Mention: Notting Hill, which turns Hugh Grant into the most nebbishly charming man on the planet. Famous or not, who wouldn’t want to be with him? It’s those damn goggles. They’re irresistible.