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— Kerry Smith
The pimples. The peer pressure. The prom. For many of us, being 16 was anything but pleasant: It was downright hell! Luckily, one can ease the pain by watching the likes of Lindsay Lohan, Molly Ringwald and Ralph Macchio pass over the most awkward of speed bumps on the road to adulthood. MTV examines the pangs of being a teenager by daring to relive every, like, totally embarrassing moment of it, one classic film at a time, discovering what the characters in these films knew firsthand: that whoever came up with the phrase "sweet 16" must have had one hell of a dark sense of humor — or else, he or she was one of the popular ones. Because the rest of us barely made it out alive.
 "Mean Girls" (2004)
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In this modern-day "Heathers," Tina Fey created some of the most savage social vampires — er, popular girls — ever to hit the self-confidence-squashing cafeteria. When high schooler Cady Heron (a cunning Lindsay Lohan) takes on an A-list clique dubbed the Plastics in this adolescent tale of survival of the fittest, she soon discovers that in a world where popularity and peer pressure are currency, it's out-clique or be outcast.
"A Cinderella Story" (2004)
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Too bad she lived "once upon a time" many, many years ago, or else Cinderella would have emancipated herself from her family faster than you can say, "Brush your own hair, you cow!" Lucky for Sam Montgomery (Hilary Duff), it's the 21st century, and her Prince Charming finds her lost cell phone and helps her escape the horrible demands of a wicked stepmother and two Neutrogena-depraved stepsisters. For Sam, having a curfew may be hell, but having a hunky someone to e-mail when your home life is a bummer is better than a pair of Manolo Blahnik glass slippers.
"Donnie Darko" (2001)
Life can't seem to get much worse for Donnie Darko (Jake Gyllenhaal). The school bully is after him, his dysfunctional family thinks he's nuts, his teachers are on his back, and he feels unloved. And then he suddenly finds himself at the mercy of a sinister six-foot-tall bunny named Frank. And you thought passing calculus was tough! Donnie must fight to survive his teen years, when the pressure is enough to make someone delusional — or is it?
"Heathers" (1989)
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For most teenagers, the threat of not being popular can seem like the end of the world — in Veronica Sawyer's case, it can be downright life-threatening. So when Veronica (Winona Ryder) climbs the social ladder only to discover that she can no longer tolerate the flaxen-haired vultures running the show, she has no choice but to take revenge on them. Now all she has to do is get out of the school's most high-profile clique with her reputation — and her life — intact.
"Dead Poets Society" (1989)
In this film, Robin Williams plays the kind of teacher few of us are privileged enough to have. You know, the one who saw past your imperfections and inspired you to believe in yourself. Williams' character, John Keating, inspires a group of prep school kids long enough for them to find truth in a world full of judgmental teachers and controlling parents. With their unconventional English teacher as their guide, the boys traverse paths to self-discovery and find that sometimes it's necessary to break the rules in order to survive.
"A Night in the Life of Jimmy Reardon" (1988)
Most of us are lucky enough to make it through the tumultuous teenage years in one piece. All Jimmy Reardon (River Phoenix) has to do is survive one night, during which he has little time to prove to his girlfriend that he is worthy of her affections. The odds are against him as Jimmy struggles to endure his father's wrath, resist the allure of seducing an older woman and return dad's car undamaged. But in this race against time, responsibility and social pressures, the clock is running out.
"License to Drive" (1988)
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A license means one thing to a teenager: freedom. But for Les (Corey Haim), driving isn't just a rite of passage — it's a matter of life and death. Unless he passes his driving exam, he will miss out on the date of his life and let his friends down. So when Les fails, he does what any normal teenager would do: He takes his grandfather's Cadillac out anyway. What happens next is a series of unfortunate events exploring teenage rebellion, maturity and responsibility.
"Some Kind Of Wonderful" (1987)
Hearts, hopes and stereotypical gender roles are broken in this classic, written by John Hughes. Sensitive artist Keith (Eric Stoltz) vies for the affections of the most popular girl in school, only to discover that his female best friend has feelings for him and that the popular girl hardly knows he's alive. Hughes skillfully captures the essence of teenage love in this nostalgic film that doubles as a consoling valentine for anyone who's ever had a crush on someone out of their league.
"The Breakfast Club" (1985)
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The high school caste system was put to the test in John Hughes' timeless film in which the school jock befriends the nerd, the rich girl falls for the bad boy, and the zany odd-girl-out empties her purse — and her deepest secrets — in front of everyone. United by their disdain for their hard-nosed principal, these five students, who ordinarily wouldn't be caught dead sitting next to each other in the cafeteria, team up during detention, discovering that there's more to each other than the stereotypes that define them.
"Better Off Dead" (1985)
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John Cusack starred in this classic tale of teenage woe as the misbegotten Lane Myer, whose world crumbles after his girlfriend dumps him for a "more popular, better-looking" guy. Torn, Lane decides he has little choice but to end his suffering by committing suicide. He has a change of heart, however, when he falls for a French hottie. Suddenly armed with self-confidence, Lane strives to survive his mother's dangerous dinners, escape his pesky next-door neighbor and make it to the end of the ski race to win his girlfriend back.
"Sixteen Candles" (1984)
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It's the eve of her 16th birthday, and Samantha (Molly Ringwald) wishes she could do a lot of things. Like make her oddball, loudmouth family disappear before they can embarrass her further, reclaim her room from the strange foreign-exchange student who has taken it over, and get her crush, Jake (Michael Schoeffling), to notice her. Turning 16 may be a lot of things (awkward, embarrassing and totally mind-blowing), but Sam learns that wishes do come true in this John Hughes coming-of-age tale involving keg parties, high school sweethearts and the pangs of being different.
"The Karate Kid" (1984)
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Daniel (Ralph Macchio) finds his inner strength with the help of his Japanese karate teacher and the power of first love. When Daniel discovers that being the new kid in town is tougher than he thought it would be, he has no choice but to focus on his karate training and solve his bully problem himself in this classic teenage melodrama about self-confidence and self-discovery.
"The Outsiders" (1983)
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Francis Ford Coppola captures the essence of teenage rebellion and the price paid for coming from the wrong side of the tracks in a film about a group of boys growing up in a town full of suspicious strangers and rival gangs. Darrel (Patrick Swayze) is forced to care for his younger brothers, the sensitive dreamer Ponyboy (C. Thomas Howell) and the rough-around-the-edges Sodapop (Rob Lowe) in this film that proves that being young isn't as easy as it looks.
"Fast Times at Ridgemont High" (1982)
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For Jeff Spicoli (played by a long-haired, "duuude"-uttering Sean Penn), high school is all about mastering the three basic subjects: sex, drugs, and rock and roll. But as Jeff and his friends ultimately learn, there's more to life than getting into the right parties, scoring with girls and getting high — like, for instance, passing Mr. Hand's class and graduating. Cameron Crowe wrote this star-studded film about the plights of a group of teenagers growing up in Southern California.
"Carrie" (1976)
Think it's rough not fitting in at school? Try having a verbally abusive religious fanatic for a mother and being the butt of a practical joke that involves you and a bucket of pig's blood. Brian De Palma's thriller, based on the novel by Stephen King, proves that the pressures of high school and adolescence are enough to make anyone snap. Especially Carrie (Sissy Spacek), whose anger manifests itself in a dangerous way as she wreaks havoc on the school with her telekinetic powers. After watching this film, you might want to think twice about who you pick on.
"Rebel Without a Cause" (1955)
James Dean was the embodiment of teenage rebellion in this classic film about a young man with good intentions who seems to be a magnet for trouble. Not only does he feel out of place at home but as the new guy in town, it seems that Jim Stark has a lot more to prove than most kids his age. Jim must fight his way to freedom at every turn. The film is a timeless portrait of teen violence and of youths trying to fit in to a world that often offers as little mercy as it does understanding.
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