Britney Spears, Baby One More Time, 1998.

Britney Spears in the video for "...Baby One More Time" in 1998.

Courtesy of RCA

If high school had existed in Shakespeare’s day, he’d have set every battle on a football field, each stolen kiss under the bleachers. That’s because when it comes to drama, neither rotten Denmark nor fair Verona holds a candle to the modern American high school. While the Bard missed out on gymnasiums, cafeterias, and locker-lined hallways, his modern-day equivalents -- the fine poets behind our favorite pop songs -- have milked these settings for all they’re worth. This is especially true when it comes to videos. As young folks everywhere trudge back to class, we’re commiserating as best we can and celebrating the 20 best music videos set in schools. They’re loaded with sex, drugs, violence, and choreographed dancing -- just like third period.

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20. Iggy Azalea ft. Charli XCX, “Fancy” (2014)
Credit E-m-m-a, not I-g-g-y, for this brilliant piece of ‘90s nostalgia. As folks who paid attention in English class know, the basis for this video, the 1995 teen comedy Clueless, was itself based on Jane Austen’s 1815 novel Emma, a timeless tale of young people playing matchmaker and fumbling their way through various romantic misadventures. Iggy and Charli do Austen (and Clueless director Amy Heckerling) proud, portraying adolescence with the right mix of silliness and swagger.

19. P!nk, “Don't Let Me Get Me” (2001)
In the first third of this video, we meet teenage P!nk and witness some of the adolescent traumas (smelly socks, pervy teachers) that made her such a misfit adult. Life isn’t easy for this reluctant pop star, but redemption comes in the final act, when she plays a show at her old high school and tears the roof off the sucka. The best revenge isn’t living well. It’s living large.


18. Brad Paisley, “Letter to Me” (2007)
If the storyline smacks of Terminator or Donnie Darko -- Paisley sends a letter back in time to warn his teenage self about the pitfalls of adolescence -- the tone is straight-up Friday Night Lights. There are bonfires, cheerleaders, letterman jackets, and lots of pretty young things acting a fool, and yet as Paisley tells his 17-year-old self, “These are nowhere near the best years of your life.” Spoken like a guy who peaked at the right time.

17. Outkast, “Roses” (2003)
That Stankonia High School drama department sure is something. When class heartthrob Andre Benjamin debuts “The Love Below,” a slick and funny musical about the class flirt, Caroline, the innovative young dramatist wins over a skeptical student body and gets everyone grooving in their seats. Everyone, that is, except Big Boi, who storms the auditorium and instigates a knockdown, drag-out brawl between his Speakerboxx crew and Andre’s theater geeks. As the fists fly, Caroline yawns and heads for the door.

16. Gwen Stefani, “Hollaback Girl” (2004)
How does Gwen get away with rolling up to school in crazy-loud convertible, parking in what’s almost certainly a bus zone, and leading an impromptu parade through the quad and into the local supermarket, where a surge of teen spirit spells trouble for the cereal aisle? She does the English department a solid and teaches everyone to spell “bananas.” Clever one, that Gwen.

15. Lil Mama, “Lip Gloss” (2008)
There’s nothing magical about the cosmetics Lil Mama gets from her mama in the beginning of this clip. Yeah, the stuff drives the fellows nuts and wins her the school election, but this is some fish-in-a-barrel business. She’s a pretty teenage girl surrounded by hormonal boys. Short of hooking herself with a fishing lure, anything she can do to draw attention to her lips is going to boost her popularity.

14. Drake, “Best I Ever Had” (2009)
Feminist fans need not fret about this video, directed by Kanye West. Yeah, Drake plays a high school girl’s basketball coach who’s staffed his squad exclusively with buxom beauties willing to wear pink spandex, but he’s a Phil Jackson type, a real master strategist. He’s got his reasons. For instance, voluptuous ladies are tougher in the paint, and if they’re a little slow running the floor, that’s why Coach Drizzy requires them to stretch so thoroughly before games. In pairs. While he watches. It all checks out.

13. Taylor Swift, “You Belong With Me” (2009)
Johnny Football Hero always goes with Susie Pompom. Theirs is an inevitable pairing at any high school, but these hottie-on-hottie relationships have a way of fizzling out. That’s when crypto-foxy band geeks like T-Swizzy swoop in, unleash the cute, and make this crazy world seem sweet and fair, if only for 3:48 intervals.


12. Wheatus, “Teenage Dirtbag” (2000)
In the video for this Loser soundtrack cut, Wheatus frontman Brendan B. Brown sings from the perspective of protagonist Jason Biggs, a dweeby Iron Maiden fan who can’t catch the eye of his crush, Mena Suvari. Brown is well qualified to provide Biggs’ internal monologue. His New Radicals-style fisherman’s hat is the only article of clothing in this amazingly dated 2000 clip that’s worse than Biggs’ winter cap, though there’s really, no shortage of fashion victims on display. What is this, Mark McGrath High School?


11. My Chemical Romance, “I'm Not Okay (I Promise)” (2004)
No one’s OK at the prep school seen in this video, a faux trailer for the greatest teen dramedy never made. Here, the angsty outcasts eat crayons and drink potions concocted in biology lab, and everyone -- even the poor school mascot -- is somehow being used and abused. The bad vibes come to a head in the closing seconds, as emo boys with croquet mallets prepare for war with the jocks on the lacrosse team. A decade after the song’s release, fans are still awaiting the big-screen resolution.

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