Some of the only solace that comes from the weird, hormone-fueled, peer pressure-riddled world of teenagerdom is watching stories you can relate to on the silver screen. Even when the story is a little over-dramatic, there’s always something comforting and familiar about watching the slightly awkward yet subtly beautiful protagonist go through the highest of highs and lowest of lows as she tries to navigate the concrete jungle of high school. The songs that soundtrack these movies still transport teenage kids of the 90s back to a simpler time, when finding a job wasn’t even on your radar, the thought of rent was ridiculous and your biggest worry was whether you were going to pass your end-of-year exams and get asked out on a date. From the tunes that accompanied declarations of love in 10 Things I Hate About You to ugly-duckling-to-beautiful swan moments in She’s All That, here are our favorite songs from our favorite coming of age movies.
Why Can’t I – Liz Phair (13 Going on 30)
Jenna Rink thinks she has the social equivalent of Willy Wonka’s golden ticket in 13 Going on 30 – the chance to erase what really happened in her dorky teenage years and do things right. The film follows Jenna as she gets her wish to fast forward to a future where she’s “30 and flirty and thriving” as a high-flying magazine editor. However, when she reconnects with her old childhood friend Matty, she realizes that everything she thought she wanted wasn’t quite what it was cracked up to be. The crescendo moment between Matty and Jenna (played by Mark Ruffalo and Jennifer Garner) is soundtracked by this underrated gem by Liz Phair. With lyrics like “Why can’t I breathe whenever I think about you, why can’t I speak whenever I talk about you?” this song pulls on your heartstrings as the conundrum of whether they’re meant to be together unfolds. Emotional stuff.
Kiss Me – Sixpence None the Richer (She’s All That)
Laney Boggs still has a place in the heart of any girl who approached high school wanting to be a little bit different. She loves to paint, go to weird performance art shows (be silent, be still) and gives as good as she gets when a jock tries to get fresh with her. The subject of a cruel bet between characters played by Freddie Prinze Jr. and the late Paul Walker, the film follows Laney as Prinze Jr’s Zack persistently woos her in a bid to beat his rival – but ends up falling for the girl in the process. Kiss Me by Sixpence None the Richer plays as Laney undergoes a makeover before the big party. Watching her walk down the staircase in slo-mo, there’s definitely an underlying frustration that Laney, played by Rachael Leigh Cook, isn’t ugly. In fact, she’s pretty goddamn gorgeous – she only had a ponytail and glasses, people! But we’re willing to forgo the clichés because this scene is teen-dream gold. The idea that a red dress and a haircut could turn a girl “hot” would be poo-pooed by feminists the world over if the film was made today, but it remains one of She’s All That‘s most memorable moments, made especially hilarious by the tumble she takes at the end of the stairs. It’s a heartwarming reminder that while you can take the girl out of the geek, you can’t take the geek out of the girl.
Lovefool – The Cardigans (Romeo and Juliet and Cruel Intentions)
Lovefool has been catapulted to legendary status thanks to its firm 20-year place on adult contemporary radio station playlists the world over (take a drive with your mom right now and see if we’re wrong), its dreamy lyrics and the way it underpins Baz Luhrmann’s incredible 1996 film adaptation of Romeo and Juliet. Shakespeare’s tale of can’t-live-without-each-other love translates perfectly for anyone who’s ever met someone special across the lunch hall – and to see it played out on screen by a devastatingly attractive young Leonardo DiCaprio and Claire Danes made you believe that your love was forever, even though you were actually lucky if it lasted past the school bell. Lovefool is such an iconic coming of age movie song that it also featured on the soundtrack to everyone’s favorite dark twisted teen fantasy, Cruel Intentions.
(You Drive Me) Crazy – Britney Spears (Drive me Crazy)
Drive Me Crazy the movie didn’t quite reach the lofty heights of others on this list at the box office – but more fool us, because the cast and story are both fantastic. Melissa Joan Hart, who after Sabrina the Teenage Witch and Clarissa Explains It All, is pretty much a coming of age icon, plays Nicole Maris, a girl who schemes with her ex-best friend and neighbor to win back their respective love interests after they’re both unceremoniously jilted before the school’s centennial party. You’ll have to watch to find out exactly what goes down, but Britney Spears’ banger of the same name perfectly sums up the love-hate-love relationship between Nicole and Adrian Grenier’s character, Chase Hammond. Melissa also makes a cameo in the video as Britney and her friends perform a dance breakdown that reminds us of the singer’s classic VMA performances. What a time to be alive, eh?!
Blinded by the Lights – The Streets (Kidulthood)
Noel Clarke’s Kidulthood resonates with anyone who grew up in inner cities up and down the UK in the late 90s and early 00s. His gritty depiction of a bunch of kids from Ladbroke Grove and the sex, drugs and violence that rips apart their lives apart forever is a story exploring themes that are alarmingly frequent in British adolescence. In the film, Trevor and Alisa both grapple with important life decisions as they walk through London’s streets soundtracked by Mike Skinner’s epic Blinded by the Lights. The song is hugely emotive and sullenly contemplative, as Skinner describes a night out where he can’t find his friends and decides to spend his time taking drugs in the club taking instead. Deployed here, it’s a vital tool in telling a different, very British kind of coming of age story.
Can’t Take My Eyes Off You – Frankie Valli (10 Things I Hate About You)
Patrick Verona’s grandiose gesture to capture Bianca Stratford’s affections makes for one of the best renditions of Can’t Take My Eyes Off You ever – even better than the karaoke versions you hear on beach vacations. His version comes complete with a brass band and, erm, getting chased by school security. This film, a modern-day version of Shakespeare’s Taming of the Shrew, is one of the era’s best-loved teen movies and boasts a stellar young cast including Julia Stiles, Heath Ledger, Joseph Gordon-Levitt, Larisa Oleynik (anyone remember Alex Mack?!), Gabrielle Union and teen movie stalwart Andrew Keegan. Other highlights of 10 Things? Bianca’s drunken table dance to Notorious B.I.G’s Hypnotize and the poem she reads to Patrick after she’s found out he’s betrayed her – when she realizes that despite his “big dumb combat boots” and the way he cuts his hair, she still doesn’t hate him, “not even close…not even a little bit… not even at all.”
Credits
Text Lynette Nylander