The 10 Best Movies of the 2000s

Time and time again, I’ve heard people say they don’t like movies, and I swear to God that I will never understand those people. Do you not have a soul? Were you not breastfed as a child? What the fuck are you talking about you don’t like movies?

Well, I do. A lot. So I made a list of the best ones from the first full decade I’ve conquered in this mundane existence of mine. A warm reminder: THIS LIST IS MINE AND I HAVE NOT SEEN EVERY MOVIE RELEASED BETWEEN 2000 AND 2009. I have not seen Eternal Sunshine of the Spotless Mind, Mulholland Drive, or any of the Lord of the Rings movies. Cue the gasps.

Anyway, let’s do it.

10. Million Dollar Baby (2004)

Starring: Clint Eastwood, Hilary Swank, Morgan Freeman

The legend Ari Gold said it perfectly: “Hilary Swank has a vagina and she won an Oscar pretending she has a dick. That’s what actors do: they pretend.” Half of me put this at #10 because it showcases Eastwood’s filmmaking skills in peak late-period form. The other half chose it because of Hilary Swank’s performance as a repressed waitress entering the masculine microcosm of boxing. Be warned, this movie will depress the hell out of you. But they make fun of it in Scary Movie 4, so check that out if you want to make light of quadriplegia.

9. Up in the Air (2009)

Starring: George Clooney, Vera Farmiga, Anna Kendrick

This flick is the reason why George Clooney is considered the unattainable, unmarriageable poon slayer we all know and love. Up in the Air is about a guy who goes around the country laying off hundreds of people during a recession. Beneath the surface, it’s really about a guy who’s ironically found solace in loneliness and eventually realizes how demented and sad that lifestyle is. It has humorously honest direction from Jason Reitman (Thank You for Smoking, Juno), our beloved Anna Kendrick, and an enthralling sense of melancholy. I lost you at Anna Kendrick, didn’t I?

8. The Incredibles (2004)

Starring: Craig T. Nelson, Holly Hunter, Samuel L. Jackson

I have yet to see a more versatile film than The Incredibles. It has every quality you would find in a good movie but rarely ever see because many of these qualities usually aren’t meant to be together. How the hell do you combine family, superhero, midlife crisis, existential, and violent elements into one coherent movie? An ANIMATED KIDS movie for that matter? In true Pixar fashion, the animated team over there in Emeryville, California, made another masterpiece that resonates with kids looking for a colorful time and adults looking for clever writing. Apparently a sequel is in the works right now, which I’m more excited for than any 21-year-old probably should be.

7. Inglourious Basterds (2009)

Starring: Brad Pitt, Christoph Waltz, Michael Fassbender

Inglourious Basterds is on this list for two tremendous reasons. First, Quentin Tarantino’s (Kill Bill, Django Unchained) rapid-fire dialogue is typically brilliant because of its attention to various European dialects and representation in the film’s heavy subtitle use. The second reason is Christoph Waltz as SS Colonel Hans Landa. There’s so much that makes Hans Landa the best villain I’ve ever seen on screen. He personifies all of the most dangerous and hateful qualities we could ever associate with Nazi Germany: cruel, calculating,, ruthless, and deceptively polite. Tarantino hit the fucking jackpot when he stumbled upon that cheeky Austrian genius.

6. Sideways (2004)

Starring: Paul Giamatti, Thomas Haden Church, Virginia Madsen

If you’re a fan of Alexander Payne (About Schmidt, Nebraska), you know he’s a man in love with highways and interstates. In Sideways, he hits Wine Country in Northern California with Paul Giamatti, a divorced, depressed writer who REALLY loves his wine, and Thomas Haden Church, a soon-to-be-married actor and Giamatti’s college roommate. Sideways’ foundation centers on Giamatti’s character, a seemingly normal guy overcome with so much loneliness and misdirection that you can’t help but cringe every time he interacts with another human being. It’s a two-hour examination of contemporary sadness that rewards viewers willing to accept its minimalist pace.

5. A Serious Man (2009)

Starring: Michael Stuhlbarg, Richard Kind, Adam Arkin

If you’re already pissed off at this list and don’t think you could possibly become any more infuriated, let me test that real quick: A Serious Man is MUCH better than No Country for Old Men. In terms of Coen Brothers filmography, I put this above No Country for Old Men and right alongside Fargo. But similar to No Country for Old Men, this movie is quiet. It’s detailed. It’s mysterious. You’ll find yourself with many unanswered questions, an often frustrating signature of the Coen Brothers that requires you to watch a couple more times. As Larry Gopnik explains in the film, “The Uncertainty Principle. It proves we can’t ever really know… what’s going on.”

4. The Departed (2006)

Starring: Leonardo DiCaprio, Matt Damon, Jack Nicholson

I know you all expected this one. It’s very, VERY safe to say that Martin Scorsese (is this really necessary?) has had one masterpiece every decade: Taxi Driver (1976), Raging Bull (1980), Goodfellas (1990), and The Departed (2006). The best thing about this movie? Mark Wahlberg in arguably his most badass role ever as Staff Sergeant Dignam. That guy would scare the living shit out of me if he were my boss.

3. United 93 (2006)

Starring: mostly unknowns

Never has a movie made me more distraught, disturbed, and overall upset. United 93 is one hour and 50 minutes of gut-wrenching tragedy, almost to the point where it is completely unbearable. But if you can stomach Paul Greengrass’ (Captain Philips, The Bourne Ultimatum) intense direction, it’s the most sobering cinematic experience you’ll ever endure. Not only is it a moving tribute to 9/11 but it’s also a testament to how ordinary people (made more effective by the lack of A-list actors) can overcome extraordinary circumstances. If you don’t believe how unsettling it is, watch the last scene.

2. The Dark Knight (2008)

Starring: Christian Bale, Heath Ledger, Michael Caine

Fuck the Academy for snipping this from a Best Picture nomination. It’s absolutely absurd how the superhero genre can be superior (no pun intended) to other genres but still it gets overlooked just because the protagonists wear capes and shit. The Dark Knight transcends the superhero genre by having a provocative philosophical core. It’s a movie that uses comic book characters to speak volumes about moral corruptibility and how chaos can easily overcome social order. This ambition couldn’t have been accomplished without Christopher Nolan’s (Inception, Memento) reliably innovative direction and Heath Ledger’s hypnotic performance as The Joker.

1. There Will Be Blood (2007)

Starring: Daniel Day-Lewis, Paul Dano, Kevin J. O’Connor

When filming for There Will Be Blood first began, an actor named Kel O’Neill was set to play the main supporting role of Eli Sunday alongside Daniel Day-Lewis. A few weeks into shooting, Paul Thomas Anderson (The Master, Boogie Nights) replaced O’Neill with Paul Dano, who had originally been cast a much smaller role. A rumor circulated that O’Neill quit because he was intimidated by DDL’s intense ability to remain in character on and off set.

Although PTA and DDL both denied the claim, it makes sense for a no-name actor to be genuinely frightened by watching DDL be consumed by a film role. You simply can’t be that good at acting without being a little bit fucked up in the head. During this epic two and a half hours, you see DDL’s Daniel Plainview descend from an ethical businessman into a milkshake-drinking savage. It’s a movie about our country’s capitalist roots, the ferocious nature of greed, and how manipulation is at the center of both.