22 Movies From 1999 You Loved & Need To Rewatch ASAP

10 Things I Hate About You has everything a teen movie from the '90s is supposed to have. And by that I mean Heath Ledger, Julia Stiles, and a musical number sung by one character to woo another.

Because that totally happens in high school in real life, right?

Sarah Michelle Gellar’s Katherine in Cruel Intentions is light years away from the character she played on Buffy the Vampire Slayer, but she makes it work.

In fact, Gellar and Selma Blair’s kissing scene won them the MTV Movie Awards Best Kiss award at the time for their joint performance in the movie.

As an adult, I know Laney Boggs (Rachael Leigh Cook) never really needed a guy to understand how much she has to offer. But as a kid watching She’s All That, I crushed on Zack (Freddie Prinze Jr.) big time.

Maybe I’m still crushing on him.

If someone had told me I would actually like a teen drama that centers around high school football before watching Varsity Blues, I would have laughed in their face.

But it’s less about the actual game and more about the underlying issues the teen players have, including Mox (James Van Der Beek), who has aspirations that go beyond high school football.

I still don't understand how it’s totally OK for an undercover adult reporter to date a teenage boy at the high school where she is posing as a student herself.

But I can let it slide for the real romance in the movie between Drew Barrymore’s Josie and the English teacher, Mr. Coulson (Michael Vartan).

The Matrix is a science fiction movie about a simulated reality in the near future and that’s all well and good. But it also combines trench coats, leather, and dark shades, which are so '90s I can't handle it.

If you have ever worked in a mundane work setting, then you can understand how the majority of the characters in Office Space grow to hate their managers and the higher ups in the companies they work for.

If not, the printer destruction scene is still worth your time.

Like everyone else who saw The Blair Witch Project when it was first released in 1999, I assumed it was a real movie from footage found in the Maryland woods after a group of film students went missing.

It’s not real, but the grainy shots and seemingly authentic conversations between the characters still make it one of the scariest found footage horror movies I have ever seen.

This movie is for every eighth grade boy who ever wanted to quote a PG-13 raunchy comedy in their worst British accents.

I’m still a sucker for Mike Myers though, and caricature of James Bond or not, I am guilty of rewatching the Austin Powers movies well into adulthood.

I admit that I only just saw The Sixth Sense for the first time a couple of years ago, but the twist at the end and the horror elements thrown in still stand the test of time.

It's also an M. Night Shyamalan movie, so if you love everything else he has created over the years (which I do), then you will be met with disbelieving faces if you say you have never seen The Sixth Sense. I speak from experience.

This is admittedly the only Star Wars movie I have ever seen in the movie theater, but that just says how important it was for the franchise at the time.

It was the first movie of the prequel trilogy and was released more than 10 years after the preceding Star Wars movie. It was a big deal, and not just because Natalie Portman was the female lead.

Notting Hill is, and will always be, a classic romantic comedy with a predictable ending and story you might have heard before.

But if you don't swoon over Julia Roberts when she says her famous speech: "I'm just a girl, standing in front of a boy, asking him to love her," then I can't help you.

American Pie is about a group of high school seniors who make a pact to each lose their virginity by the end of the school year.

It's hard to root for any of them with that kind of attitude about sex, but they aren't all Stiflers and that’s what is important.

We have all known a Tracy Flick (Reese Witherspoon) at some point. She is the overachieving student who will stop at nothing to win a school election and takes things like high school government way too seriously.

Watching her in action as she essentially torments Mr. McAllister (Matthew Broderick), who tries to guide a directionless jock (Chris Klein) to run against her is still entertaining, though.

Hilary Swank won the Oscar for Best Actress for her role in Boys Don't Cry and for good reason. She plays Brandon, a transgender man who is targeted after an ex-girlfriend’s brother finds out he transitioned from female to male.

Throughout the movie, he is beaten and treated horrendously while trying to find his place and maintain a relationship. It's heartbreaking and powerful.

Jawbreaker shows what happens when a clique of all-too-powerful teenage girls accidentally kills one of their own and covers it up while initiating a new member into their group.

It’s not a story meant for realism and at times it can be ridiculous, but it was the '90s. I think we can let it slide.

It wasn't a teen rom-com or a drama worthy of Oscar-winning status, but Toy Story 2 continued the monumental computer animated adventures of Buzz Lightyear (Tim Allen), Woody (Tom Hanks), and all of their talking toy pals.

Idle Hands might have flown under the radar for some, especially since 1999 birthed a ton of memorable movies, but it was the perfect dark comedy of its time.

When Anton (Devon Sawa) finds out his hand is possessed by a demonic force, his usually boring life is turned upside down and his hand literally leads him on a path of destruction.

When Leigh Ann's (Katie Holmes) chances of becoming valedictorian are put in jeopardy by grades given to her by her English teacher, Mrs. Tingle (Helen Mirren), she has no choice but to gather her besties, kidnap her teacher, and force her to change her scores.

Because things will totally end well for everyone involved, right?

Girl, Interrupted is a who’s who of celebrities who rose to fame in the late '90s.

The movie follows Susanna (Winona Ryder) as she navigates a women's mental health clinic in the '60s and encounters other women with troubles of their own, including characters played by Angelina Jolie, Elisabeth Moss, Brittany Murphy, and Clea DuVall.

If you think Matt Damon only has the ability to play the nice adoring guy, then forget everything you thought you knew about him before watching (or rewatching) The Talented Mr. Ripley.

Set in the '50s, Tom Ripley (Matt Damon) is tasked with bringing a man’s wild entitled son Dickie (Jude Law) back home.

But when he meets him, he decides he will stop at nothing to have Dickie’s life, including the love of Dickie’s girlfriend, Marge (Gwyneth Paltrow). Is it just me or can only wealthy people from the '50s get away with names like Dickie?

I’m sure Hollywood will keep churning out hits that rival those of 1999, but I will never not have 10 Things I Hate About You in my personal top 10 list. And The Blair Witch Project will forever be a horror classic, despite everyone now understanding that it was a fake found footage movie.

1999 was a memorable year for movies across almost all genres and if this hasn’t inspired you to rewatch all of your faves from 1999 right now, then we can't be friends.