Top Ten Films of 1999

Yes, we have come to the final year of the decade. Y2K was stopped. If you think that was just a silly thing dumb people were scared of over 2 decades ago maybe go look that up. Some anonymous computer programmers saved all of us in a short amount of time.

Columbine shooting

an F5 Tornado sweeps through Oklahoma

Napster debuts

JFK Jr’s plane crashes

Stanley Kubrick passes away

The SEGA Dreamcast is created

The year in movies was dominated by Phantom Menace, not on this list, and The Sixth Sense. I wish that could happen today.

Here’s my 11-25 in alphabetical order.

10 Things I Hate About You (Directed by Gil Junger)

Audition (Directed by Takashi Miike) - Shudder

Austin Powers: The Spy Who Shagged Me (Directed by Jay Roach)

Big Daddy (Directed by Dennis Dugan)

Dogma (Directed by Kevin Smith)

Eyes Wide Shut (Directed by Stanley Kubrick)

Julien Donkey-Boy (Directed by Harmony Korine)

Life (Directed by Ted Demme) - HBO Max

Man on the Moon (Directed by Milos Forman)

Office Space (Directed by Mike Judge)

The Green Mile (Directed by Frank Darabont)

The Insider (Directed by Michael Mann)

The Sixth Sense (Directed by M. Night Shyamalan)

The Virgin Suicides (Directed by Sofia Coppola) - Amazon Prime & Criterion Channel

Toy Story 2 (Directed by John Lasseter)

10. The Straight Story (Directed by David Lynch)

Lynch is known for his eerie and supernatural films about the underbelly of America. Here, the title speaks for itself, and he keeps it simple. A man travels by lawn mower to see his estranged brother. It’s a beautiful film that should be seen by anyone and everyone.

9. The Matrix (Directed by The Wachowski’s)

If this were the most memorable or most influential movies it would be higher. I think the first hour of this is a near perfect film. The rest is good but can’t hold up to how good the first half is to me. It’s so good though.

8. The Limey (Directed by Steven Soderbergh)

It’s not his most fun, but it might be the best Soderbergh movie. He’s made the last two top ten lists and I know he will continue to show up as these lists go on. One of his least famous casts makes the movie less memorable for some, but it’s damn good. A father on a search for his daughter and a lot of great british accent yelling.

7. The Talented Mr. Ripley (Directed by Anthony Minghella) - HBO Max

The first dose of Philip Seymour Hoffman on this list and although he isn’t in this but maybe 10 minutes he makes an impact. The biggest impact here is just how good this young cast was. Paltrow continues her late 90’s dominance, and Jude Law looking perfect embodies the character everyone wants to be. Most of all, Matt Damon. Who is never better than when he creates a weasel, conniving little psycho.

6. The Mummy (Directed by Stephen Sommers)

Such an important movie to my development. Watching this after school in 3rd grade taught me a lot of things. Like how bugs crawling under skin is my number 1 fear. This is an Indiana Jones movie for the generation that grew up on video games. That a woman fully dressed, running a library, bumbling around, and not taking any shit is my type. And I love it. This is in the top of my 90’s movie canon and I am so glad it holds up enough for me to include it here.

5. The Iron Giant (Directed by Brad Bird)

Maybe the most inadvertently political movie. Or it was on purpose, but either way it almost makes me cry every time. It’s a gorgeous movie that every kid should see and any adult who hasn’t in a while or not at all should make time. I get so much from this movie.

4. Bringing Out The Dead (Directed by Martin Scorsese) - Amazon Prime

One of Scorsese’s forgotten classics. Nicolas Cage brought calm restraint and respect to this movie about a burnt out EMT that sees the dead. It’s a great script brought to life with the vigor of any great Scorsese movie. The rest of the cast is top notch with Patricia Arquette, John Goodman, and Ving Rhames.

3. Being John Malkovich (Directed by Spike Jonze) - Netflix

Another one that gets better each time. Kaufman scripts will do that. Removing layers more and more as you go. It’s maybe my favorite concept for a movie ever, and it’s easily Cameron Diaz’s best performance. You have no excuse not to see this.

2. Fight Club (Directed by David Fincher) - HBO Max

Not much needs to be written here. It is a polarizing mess of a movie that I love so much. It is funny, gross, mesmerizing, and menacing to all the right people. It’s perverted, just like the best Fincher movies.

1. Magnolia (Directed by Paul Thomas Anderson) - HBO Max

PTA once said he would go back and cut 40 minutes out of this thing. He regrets how much of an indulgent pompous ass he was when he was young. But, I’m so glad he was. The score, relentless pace, and performances make this one of my all time favorites. I love each storyline, and I get so wrapped up each time it comes on. Tom Cruise is at his best here.