There was a period of time in the late '90s and early aughts that was particularly great for the teen rom com. Whether due to the apex of the Disney Channel Original Movie or attributable to the success of films like Legally Blonde, these movies proposed different views of femininity and espoused a girl-power perspective that was totally necessary for young women coming of age at the turn of the 21st century. Though this list focuses on teen movies from the late '90s and early '00s that are currently available to stream, there are a whole lot more gems — Bring It On, Never Been Kissed, and Freaky Friday among them — that aren't available on streaming services.
Yet. Netflix and its peers constantly cycle through new selections of old favorites. So while this list reflects what's currently available on Netflix and Amazon Prime streaming, there are sure to be old favorites beyond these eight becoming available in future months. But be warned — Netflix often discards some of its old films at the same time as it welcomes new ones, so catch these movies before they're gone.
Though teen titans like John Hughes' brat pack films of the 1980s often receive their share of the attention as teen films that still hold up decades later, more recent movies often get short-shrift. Perhaps they haven't had enough time to become appreciated as they're due, but many more recent ones (Mean Girls chief among them) are modern classics that will only grow finer as time passes. They're both a testament to the power of women holding their own against men in films and an homage to a particular time and place in teen-directed filmmaking. They clearly owe a lot to John Hughes and his ilk, but they also have a style all their own.
1. The Prince And Me (2004)
Prince Edward of Denmark just wants to be like any other college kid. And Julia Stiles plays, well, any other college kid — a brilliant medical student who doesn't realize that her charming suitor is actually royalty. She finds out after an embarrassing paparazzo incident, and feeling betrayed, it looks like the end of their relationship. Don't watch the trailer if you want the rest to remain a mystery, but know that it features a Pretty in Pink-esque pink gown, culture shock, and probably a very happy ending.
2. Cadet Kelly (2002)
High school fashionista and sometime-trouble maker Kelly is shepherded off to military school when her family decides she's a bit too much of a handful to stay home. In search of a little discipline, they pack her off to an academy also populated by Christy Carlson Romano, who plays an uptight drill captain. Though they rub each other the wrong way at first, they team up to take on baton twirling and the powers that be at the school side by side.
3. 13 Going On 30 (2004)
Jennifer Garner's magnum opus. If you haven't seen it already, clear your afternoon schedule. It definitely has a broader audience than just teens around the early 2000s, but that's just because no woman can't relate to Garner's excitement at finally developing "great boobs!"
4. Holes (2003)
Just as Louis Sachar's book of the same name will forever be a childhood-defining classic, the film adaptation it spawned still holds up more than 10 years later. Particularly worth your time is the soundtrack that features "Dig It," a silly rap-inspired romp that features each of the characters showing off their hip hop chops.
5. National Treasure (2004)
"I'm going to steal the Declaration of Independence." The only Nicolas Cage film worth your time.
6. Spy Kids (2001)
One of the earlier movies on this list, Spy Kids offered its kid audiences a chance to grow up alongside Alexa Vega's Carmen. She and her brother returned for several Spy Kids sequels, in which the brother and sister pair follow in their international spy parents' footsteps. The thumb things are still the stuff of nightmares.
7. Drive Me Crazy (1999)
After Melissa Joan Hart and Adrian Grenier are both spurned immediately before a huge high school dance, they team up — and Hart's character gives Grenier an extensive makeover, demanding both to ask who they really are underneath the veneer of high school identity. It might be named for the Britney Spears song "Crazy," if that's any motivator. (In any case, the song features in the trailer.) And while it wasn't the biggest hit back in '99, in retrospect, it's a pretty cool meditation on what it means for your identity to be a "scam," as they repeat throughout the movie.
8. Mean Girls (2004)
This movie spawned its own holiday. How many teen favorites can say that?
Teen movies explored a wide variety of themes in the late '90s and early '00s, from where men and women fit into social hierarchies to how best to channel your true self. These are themes that still hold up years later — so here's hoping that many more like-minded movies end up on streaming services in the months and years to come.
Image: Paramount Pictures