18. Good Will Hunting (1997)
Matt Damon and Ben Affleck originally wrote a script about a gifted young man who gets recruited to the FBI so they can use his talented mind to catch criminals. Director Rob Reiner read the script and made a few suggestions. A few years later, Gus Van Sant agreed to direct and the rest is history.
We follow a young MIT janitor whose mind is a complex maze of genius. When the staff takes notice, he is passed over to Robin Williams (in his greatest role) as a psychiatrist desperate to push the young man to his full potential. His best buddy Ben Affleck and a love interest played by Minnie Driver stand in his way.
But that’s what is great about this film – it doesn’t blame Damon’s character of his personal life; it lets him choose. Sometimes we have talent but it’s ultimately our choice on what we want to do with ourselves. This sweet culturally engrained drama earned them an Oscar for Best Screenplay and a reserved spot in Hollywood.
19. Rushmore (1998)
No one can make a movie like Wes Anderson – and we certainly don’t want anyone to try. With forgotten sixties songs, bright rainbow colors, the Wilson Brothers and Bill Murray popping up in random scenes – there’s just a certain style you just can’t match.
This was the film that opened everything up to mainstream audiences; it was the first pairing between Anderson and Murray (who had hit a career slump around the same time). And it also launched the career of character actor Jason Schwartzman. Here, he plays a bizarre over achiever who falls in love with his teacher.
While he tries desperately to win her affection, Bill Murray’s sad Herman Blume begins to simultaneously compete for the same thing. Laugh out loud hilarious and strange – the beautiful world Anderson creates helps illustrate themes of infatuation, determination, loss, and of course not being able to fit in.
20. Can’t Hardly Wait (1998)
If there ever was a time capsule to preserve young actors before they were famous – this one is it. Can’t Hardly Wait actually is a time capsule of that strange late nineties time filled with skateboard music, frosted tips, and the dawning of the internet.
We follow Jennifer Love Hewitt, Seth Green, Ethan Embry, and a slew of other teens on grad night, searching for love and a sense of future at a party. Sure, it’s been done before (although this one begins and ends at the bash), but it illustrates so many elements that were popular at the time.
The music, the clothing, the ways of thinking; the film was a blip on people’s radar when it came out, but upon further watching it does contain many relatable elements that will resonate with recent graduates. Filled with booze, sex, and typical teenage things – it was a precursor for the explosion of recent low brow teen comedies.
21. American Pie (1999)
Speaking of – this one is the king of the genre! Why? Simply because a long gap between teen gross out films left eagerness in many youngsters souls. The nineties were filled with heavy dramas or blockbusters. It was time to go back to the eighties and resurrect one of the most popular, possibly warn out genres.
In American Pie, high school seniors try to lose their virginity before graduation – that’s the set up. Along the way they mess up heinously whilst trying a practice run on a pie and enduring advice from one of their nerdy father’s (played by a never named Eugene Levy).
It’s crass, silly, and even dumb – but there is a sort of sweetness to it when you look at the relationship between Father and Son and even friends. It was simply in the right place in the right time and became a classic – focusing on a very relatable topic. Sequel after sequel after sequel have ensued – never reaching the popularity of the first.
22. 10 Things I Hate About You (1999)
Another “Before They Were Famous” snapshot – 10 Things combines classic Shakespearian literature (the basis taken from Taming of the Shrew) with modern day style and music.
A nerdy and very young Joseph Gordon Levitt wants to date a girl in his class but discovers her Father has a rule that if her sister doesn’t date – neither can she. So he sets off to find the sister a perfect match, or the first willing participant (enter Heath Ledger).
This career making role catapulted the hunky Aussie into stardom and fame – especially when he gets behind a microphone and belts “Can’t Take My Eyes Off of You.”
The task in the film isn’t easy since the sister is stuck up and very hated indeed. What we can take from 10 Things besides a fun time is lessons in first loves, the dangers of high school trust, and what type of list you should make when your heart is hurting after a break up.
23. American Beauty (1999)
Here’s an instance where the character comes of age much later down the line (or reverts back to those simpler days). Meet Lester Burnham, an Oscar winning Kevin Spacey who hates his job, family, and life. So he quits by black mailing his boss, begins to work out to impress his teenage daughters best friend, and starts smoking pot courtesy of his peculiar next door neighbor.
Simultaneously his teenage daughter is experiencing first loves, experiments with drugs, and suffers from pressures in school. It’s a busy movie but director Sam Mendes manages to keep everything on track and in place.
We get a comparison of young and old – maturing and de-maturing… or finding a balance for everything. It’s a complicated film but it highlights peer pressure so well. No matter how old we get, we can’t escape it whether it’s the pressure to have sex, take drugs, or keep up with your rich neighbors down the street.
24. Varsity Blues (1999)
Where would a coming of age list be without a good football movie? Though the plot has now been overshadowed by the similar Friday Night Lights series, Varsity Blues remains fresh thanks to its dedicated cast.
Jon Voight leads a struggling high school team in Texas where they live and breathe the game. James Van Der Beek is the shier, quieter, intelligent backup quarterback who is thrown into the game mid season.
While it’s a thrill – the teen wants to focus on his girlfriend and schooling more than football. The previous quarterback, played by the late Paul Walker in an early role, takes issue with this and tries to force him out.
A very watchable conflict indeed – the film doesn’t step over the line of cheesy. It instead compares the value of sports and knowledge and helps a young man come of age through teamwork and standing his ground on his own beliefs.
25. The Virgin Suicides (1999)
After Sophia Coppola took some time to digest her much hated performance in the Godfather Part III, she decided to follow in the footsteps of her famous father and direct. Adapted from a bestselling 1993 novel – the film takes a look at a troubled family filled with four teenage girls and two very stressed parents.
To keep them in line, the parents enforce some very strict rules – but this only pushes this further. An apparent suicide pact leads them attempting to kill themselves.
Of course this becomes the talk of the town, leading to an investigation by a group of teenage boys. Bordering on horror – this smart and savvy seventies set movie introduces us to a grown up Kirsten Dunst and brilliantly gives us the girls thoughts via the male opinion. With so many different fresh takes – the film is wholeheartedly original.
A dissention into promiscuity (possibly due to male fantasy) this odd study on parental influence and the male psyche will leave you in awe and relief that your school years weren’t as strange.