The Top 15 Movies of 1999


Since it’s January, it’s time for every entertainment website out there to give their top 10 lists for the year. While I haven’t done that…yet, I decided it might be a little more fun to take a look to the past, specifically a decade ago to 1999, back when we were all stock piling water for Y2K. I was stunned to see how many classic movies came out that year, so I decided to compile a little list of my own, the top 15 movies of  1999.

15. Girl, Interrupted


No, sadly they never made out.

This probably would have been in the top five in most critic’s lists at the time, but not mine. It’s a decent look at life inside a women’s mental facility, but it’s certainly no One Flew Over the Cuckoo‘s Nest. The highlight had to be a young Angelina at her most insane (and it won her an Oscar), which is actually how she was acting at the time in real life, with Billy Bob’s blood vial around her neck and all.

14. Dogma


Yeah, forgot Professor Snape was in this movie didn’t you?

A lot of Kevin Smith’s most ambitious project then or since got lost to the average movie-goer, but the Catholic Church understood enough of it to get super pissed off and call for boycotts of the film. Like people who take orders from the Catholic Church were ever going to see this anyways. Matt Damon and Ben Affleck as two rampaging fallen angels is still probably one of their best roles to date.

13. Princess Mononoke


An animated movie had to make the list because Pixar didn’t put out anything this year.

Even if you didn’t like anime, if someone dragged you to an art theater to see Princess Mononoke, you couldn’t leave without thinking it was great. Even dubbed with American actors like Billy Crudup, Claire Danes and Gillian Anderson, it still didn’t lose any of it’s charm. If you missed it then (and it’s more than likely you did), it’s definitely worth a look on DVD now.

12. Cruel Intentions


What? It’s just a perfectly innocent step-brother step-sister back rub!

Oh Cruel Intentions, one of 1999’s guilty pleasures. It brough us a million classic moments in onscreen seduction and three classic characters. The womanizing Sebastian (Ryan Philipe), his hump-anything-that moves step-sister Kathryn (Sarah Michelle Gellar) and the purity case study Annette (Reese Witherspoon). The plot is literally as follows. Kathryn makes a bet with Sebastian that he can’t sleep with Annette, and if he does, he’ll let him sleep with her. Wow. Sounds like a win-win to me.

11. The Talented Mr. Ripley


“Pshh what a dork, he could never be a brilliant killer or anything.”

After Good Will Hunting catapulted Matt Damon onto the map, he landed this role as psychopathic, but subtle, killer Tom Ripley. Sure, I’m guessing we’ve all wanted to kill Jude Law at one point or another, but Ripley was brilliant, devious and more than a little creepy in doing so.

10. Eyes Wide Shut


Young Tommy Cruise attends his first Scientology meeting.

Eyes Wide Shut put the **** in ****ed up. The most Stanley Kubrick movie ever made by Stanley Kubrick, it followed Tom Cruise and Nicole Kidman around as they discovered a secret underground sex club, resulting in there being onscreen nudity for quite literally half the film, along with an orgy scene that got the film rated “X” in more than a few countries.

 9. South Park: Bigger, Longer and Uncut


 Now Sadaam is *actually*in hell! Hah.

It can be argued whether or not this was South Park’s peak (I think that happened a few years later), but it’s one of the most memorable animated ever. Known for it’s insane swear-count (over four hundred f-words alone), the most recognizable parts are the songs, which include “Kyle’s Mom is a Bitch” and of course, “Blame Canada” which was actually performed at the Oscars.

8. Lock, Stock and Two Smoking Barrels

lock stock

 I mean come on, it’s like he’s wearing a sign that says “please **** with me.”

The film that made people sit up and take notice of Guy Ritchie. Arguably better than his more readily recognized Snatch, Lock Stock features most of the same cast, and most of the same plot. If you could wade your way through the thick accents, you loved it as a film that never took two seconds to stop moving.

7. The Blair Witch Project


Ahhhh! Sticks! Run!

Before all the parodies and jokes, there was a movie made by three kids with $10 and a video camera. Or something like that. The Blair Witch Project remains today as the ultimate symbol of doing more with less (I’m not counting My Big, Fat Greek Wedding), and at the time before everyone knew the end, it was truly terrifying in parts. And it’s mostly just running around the woods with rustling leaves and distant noises.

6. American Beauty


“You better have sex with me because I just spent $6,000 on roses for this damn tub.”

American Beauty actually won Best Picture this year #6, as everything that follows from here on out just seems more well…classic. But the film is a brilliant exercise in suburban gothic, and has a whole host of unforgettable moments (the rose petals as seen above and of course, the dancing bag). Maybe it deserved to win at the time, but these next five films have proven to wear better since.

5. The Green Mile


He’s in the Street Fighter movie now. Sigh.

Yes it’s a Stephen King book, no, it’s not Shawshank. After you stopped being confused about that, The Green Mile was a phenominal film with brilliant performances from both Hanks and Clarke Duncan. That best part is when he grabbed Tom Hanks’ crotch. Heh.

4. Office Space


He made us all want to burn the building down.

I’m sure this barely made it on to any top ten lists back in 1999, but Office Space has stood the test of time more than almost all of these other films, and is recognizable as a classic today. Everyone could relate to it, everyone had that boss, everyone had that creepy guy, everyone really only did “15 minutes of real work a day.” And tell me you don’t count the pieces of flair on your waitress when you go to a restaraunt now.

3. The Sixth Sense


“I’m….going to grow up and get awkward looking. And you’re….going to go bald. Well, more bald.”

The Sixth Sense was tricky, because in order to get the most out of it, you had to sucessfully dodge people ruining the end for you before you saw it. I’d say only about 50% of people accomplished this, but if you were part of the lucky few, the movie was pretty astonishing. An exersize in suspense that really hadn’t been seen before, it was surely a sign that this M. Nigh Shyamalan was this countries next big horror director. Right? What happened with that anyways?

2. The Matrix


It’s a rule that every picture I show of Keanu Reeves on this site the caption must simply read:


Fact: Most people didn’t like The Matrix right after they saw it. They were confused about what they had just seen, because they’d never witnessed anything like it. I even read a film critic who gave it one star, then months later after everyone was pouring acclaim on it, he went back and changed it to four, saying he “just didn’t get it before.” The Wachowski’s vision of the apolcalyptic future may not have held up over three movies, but the original is a sci-fi/action classic and with “bullet-time” revolutionized the way action films are shot to this day.

1. Fight Club


I mean, it’s no “Never Back Down.”

Ten years ago David Fincher directed Brad Pitt in a movie that didn’t involve backwards aging or special effects makeup. And as Benjamin Button may very well could be the best film of this year, Fight Club was certainly the best of a decade ago, despite not being recognized with awards or critical accolades. It was shocking, haunting and had an ending that if you claim you guessed, you’re lying. It created Tyler Durden, one of the most iconic onscreen characters ever, and made everyone quietly ask themselves, “How much can you really know about yourself if you’ve never been in a fight?”

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  1. Never realized how many great movies came out the year I graduated high school. Must be because I was wasted every day and spent all my money on booze instead of movie tickets.

    But gotta agree with Shamus, Blair Witch still owes me the $6 or so (forgot how cheap it was back then) I spent to actually see that one. Sure wish I’d have seen some of these others instead.

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