Echoing Jane Austen’s Emma, Clueless follows California girl Cher Horowitz (Alicia Silverstone) as she tries to play matchmaker at her school – with disastrous results, obviously. Despite being rich and popular, Cher is well-meaning and sweet, and takes a nerdy new girl called Tai Frasier (Brittany Murphy in a breakout role) under her wing. Eventually, Tai becomes more popular than Cher, leaving our protagonist to question her priorities and motivations.
Clueless frequently pokes fun at Hollywood conventions; at the beginning of the movie, we find out that Cher’s mom died tragically from complications of a liposuction surgery. Though I was deeply weirded out by the fact that Cher’s love interest was her ex-stepbrother (played by Paul Rudd), I loved the movie’s flamboyant outfits and snappy dialogue.
Memorable scenes: Cher’s soul-searching and lonely shopping spree in Beverly Hills, Cher dubbing her rival Amber a “Monet” (“From far away it’s OK, but up close it’s a big old mess.")
Spice World (1997)
Though more tween movie than teen movie, Spice World perfectly encapsulates the girl power mania of the mid- to late-90s. The movie is so bad it’s good, holding an abysmal 29% rating on Rotten Tomatoes. The wafer-thin plot makes no sense and the girls can barely act, but the songs and rollicking scene changes make for many moments of high camp.
Spice World has huge nostalgia value for those of us born in the mid- to late-80s. Shiny platform boots? Check. Mel C’s leopard print catsuits? Check. Performances of “Too Much” and “Spice Up Your Life?” Check.
Memorable scenes: The Spice Girls dressing up as each other for a photo shoot (there’s nothing more awkward than Victoria Beckham imitating Baby Spice), a cameo by Roger Moore as the mysterious record label owner, Posh Spice speeding in the Spice Bus to Albert Hall
Romeo + Juliet (1996)
Love it or hate it, Baz Luhrmann’s over-the-top Shakespeare adaptation never fails to elicit a reaction. Romeo + Juliet launched romantic leads Leonardo DiCaprio and Claire Danes into stardom, cementing their reputations as teen idols.
The movie holds a special place in my heart. I was dazzled by its tragic account of doomed lovers, lavish costume designs, excellent soundtrack (which I still own on CD), and gritty modern-day backdrops. There are lots of clever references to the original play; for example, the guns used by the dueling Capulet and Montague families are all named after bladed weapons: “Dagger,” “Sword,” and so on.
Memorable scenes: Romeo and Juliet’s first meeting through a distorted aquarium glass, the Capulets’ extravagant costume party, Romeo’s epic chase scene with Tybalt
Wes Anderson’s first directorial feature follows oddball teenager Max Fischer (Jason Schwartzman), a 15-year-old student at an all-boys school who has the distinction of both being in the most extracurricular clubs and having the worst grades. He befriends a rich businessman named Herman Blume (Bill Murray), and they both fall in love with a teacher at Max’s school, Rosemary Cross (Olivia Williams).
Many of trademarks that would go on to characterize Anderson’s films are present in Rushmore: the eclectic soundtrack, off-kilter humor, immaculate set design, and deadpan acting. The movie is a gem, both wonderfully acted and presented.
Memorable scenes: The opening montage showing all the clubs that Max has joined or formed, Max and Herman’s back-and-forth acts of revenge for Rosemary’s love, Max’s original play at the end
Rebel Without a Cause (1955)
The original teen rebellion movie, Rebel Without a Cause stars the immortal James Dean, who tragically died a few weeks before the film came out. Without a doubt one of the best-acted and most poignant movies on this list.
In Rebel Without a Cause, 17-year-old Jim Stark (Dean) frequently gets in trouble with the law and feels misunderstood by his parents. He encounters a bully named Buzz at his new school, but soon becomes friends with fellow misfits Plato (Sal Mineo) and Judy (Natalie Wood). Throughout the film, they struggle with generational differences and society’s attitude towards youth. If you’re not in tears by the last scene, you’re an unfeeling rock.
Memorable scenes: Jim and Buzz’s blood-pumping “chicken run” race; Jim, Judy, and Sal playing “house” by acting out the perfect family; Sal’s confrontation with the police