20. King Kong (dir. Peter Jackson)
Believe it or not, kids, there was a time when special effects were actually special. When movies were filmed on actual sets. When digital environments were carefully rendered and not sloppily rushed out to meet a quarterly earnings call. Peter Jackson’s adaptation may be as large as the Kong himself, but there’s still the same movie magic present in all three Lord of the Rings movies. And once again the MVP is Andy Serkis, bringing to life a fictional creature with astonishing presence.
19. Batman Begins (dir. Christopher Nolan)
A comic book origin story that puts others to shame. Batman Begins is miles away from Joel Schumacher’s maximalism, but it’s not without its own sense of humor. Years before he got typecast as a man with a “particular set of skills,” Liam Neeson delivered one of the best villain turns of the decade as Ra’s al Ghul, whose contemptuous view of mankind sounds like a precursor to Thanos. Nolan would perfect his vision of Gotham a few years later, but this grounded starting point remains highly watchable, and a reminder of a time when superhero movies didn’t come with homework.
18. The 40-Year-Old Virgin (dir. Judd Apatow)
It’s crazy to think how different the comedy landscape would be now if this hadn’t been a hit. It’s unlikely The Office would have become a phenomenon. Seth Rogen wouldn’t be an impresario. Paul Rudd might still be doing guest arcs on sitcoms instead of playing a superhero. But everything about Judd Apatow’s sweet-but-naughty rom-com works, from Carell’s sincere turn to the tender relationship he develops with Catherine Keener’s single mom. It also helps that it has one of the funniest scenes ever, with improvised faux-profanity and genuinely horrified reactions.
17. Grizzly Man (dir. Werner Herzog)
An essential nature doc whose message is not conservation or wonder, but staying the fuck away from dangerous animals.
16. Downfall (dir. Oliver Hirschbiegel)
Anchored by a titanic performance from Bruno Ganz, Downfall captures the bleak final days of Hitler’s reign. It’s not a humanizing portrait by any means, but it does cut an almost mythically evil figure down to size. As the walls close in, he’s all too eager to blame anyone but himself for losing the war he escalated at every turn. That its images of Berlin could soon mirror Washington, D.C. just makes the film that much more powerful.
15. A History of Violence (dir. David Cronenberg)
It took a Canadian to accurately dissect (or vivisect… this is Cronenberg we’re talking about after all) the distinctly American obsession for blood and vengeance. Viggo Mortensen gives his greatest performance as Tom, whose presentation as a completely average nobody gets disrupted in horrifying fashion after he thwarts a robbery and assault. The media attention brings his brother’s henchmen out to disturb his peaceful life. But it’s the fraying of his family that hurts more than any flesh wound. With an iconic one-scene turn from William Hurt (in an Oscar-nominated performance), this film appears lean and mean on first watch. But it reveals itself to be much deeper every time you revisit it.
14. The Squid and the Whale (dir. Noah Baumbach)
I haven’t always dug Baumbach’s prickly dramedies. But in another case of a film being deeper than it first appears, The Squid and the Whale delivers. Featuring a star-making turn from Jesse Eisenberg, he stars as Walt, a smart yet adrift teen dealing with his parents’ messy divorce. Jeff Daniels steals the show as his arrogant professor dad, whose perfectly timed mid-life crisis throws an already tense situation into full-blown chaos. This is an ideal entry point into Baumbach’s work, if you’ve ever wondered what the big deal is.
13. Layer Cake (dir. Matthew Vaughn)
The aughts saw no shortage of ultra-slick crime movies. But while many were content to rip off Quentin Tarantino (or the fleet of copycats), Matthew Vaughn delivered the goods with Layer Cake. (The less said about his later films, the better.) Daniel Craig nailed this feature-length audition to become James Bond as a nameless protagonist forced to pull one last job for the organized crime outfit he works for before retiring. The twists pile up, but it’s all done with impeccable style.
12. The Constant Gardener (dir. Fernando Meirelles)
Spoiler alert: This movie is a huge bummer. (It’s not the biggest bummer on the list, though.) Still, it’s appropriately bleak and realistic, exposing how major corporations hold more sway over geopolitics than elected officials or citizens. Anyone getting in the way of their profits will find themselves in the gunsights.
11. Millions (dir. Danny Boyle)
The Oscar-winning director’s most underrated film, Millions is that rare thing: a live-action film for the whole family. It’s earnest but never squishy, and features an incredible child performance from Alex Etel as Damian. It starts as your typical “find a bag of money and trouble follows” movie, but Damian’s sense of wonder and genuine desire to help people takes the film in unexpected, heartwarming directions.
10. Oldboy (dir. Park Chan-wook)
The first time you see Oldboy, it seems like showing off. And make no mistake, Park doesn’t mind flexing for his audience. But as he’s grown as a filmmaker, it’s clear the most famous chapter of his vengeance trilogy was not just provocation. This is about as disturbing, entertaining, and compelling as modern movies get.
9. Kingdom of Heaven (dir. Ridley Scott)
I was a fan of Ridley Scott’s epic tale of the Crusades even when it was first released in truncated form in the summer of 2005. But his director’s cut – which includes both an overture and intermission – makes it into a masterpiece. Brutal, thought-provoking, and awe-inspiring, it’s even better than Gladiator. (Yes, I said it.)
8. Good Night, and Good Luck. (dir. George Clooney)
This low-key but moving take on Edward R. Murrow’s war with Sen. Joseph McCarthy has sadly taken on added relevance in the past year, as his home at CBS has been overtaken by the talentless sycophant Bari Weiss. She’s transformed a one-time bastion of a free and independent press into a mouthpiece for a gaudy fascist and his cronies. There was a time, not even that long ago, that journalists used their power to push back on the government, not cater to their whims. Clooney may not have had a strong career as a director, but he did make this one which will stand the test of time.
7. War of the Worlds | Munich (dir. Steven Spielberg)
9/11 broke us as a country, and it especially affected Steven Spielberg. So much so he made not one but two films about the terror and uncertainty about that day, filtered through a sci-fi epic and a ’70s paranoid thriller. The former was his big summer blockbuster, starring Tom Cruise at the height of his celebrity/craziness. He may not be believable as an everyman construction worker, but his desperation and fear as aliens destroy his home and threaten his family is all too real. The latter was his awards season favorite, a thorny film that looks much better than some of its fellow nominees and winners. Tony Kushner’s script heightens the futility of vengeance and the devastating effects of state-sanctioned violence.
6. Mysterious Skin (dir. Gregg Araki)
If The Constant Gardener and Munich didn’t hurt you enough, there’s always Gregg Araki’s crowning achievement. Based on Scott Heim’s novel, it’s an absolutely devastating story about the ripple effects of abuse. A never-better Joseph Gordon-Levitt stars as Neil, a young hustler in Kansas. His traumatic childhood has left him “with a black hole where his heart should be” and his desire to get out of his small town leads him to increasingly dangerous situations. Future filmmaker Brady Corbet plays Brian, a shy classmate trying to unravel the mystery of a horrific event from his past he can’t remember. When their paths collide, it’s a moving moment that will probably ruin your whole day (complimentary).
5. Kiss Kiss Bang Bang (dir. Shane Black)
Shane Black’s whipsmart comeback vehicle for Robert Downey, Jr. (and himself) is the most purely entertaining film on this list, unless you have an allergy to Black’s quippy writing. RDJ begins his ascent to the A-list as Harry, a two-bit thief turned actor. But Val Kilmer mops the floor with him as Gay Perry, a private detective and consultant who gets them caught in a complex murder case. Their banter paves the way for Black’s masterwork The Nice Guys, but don’t “feel badly” for these dopes.
4. The New World (dir. Terrence Malick)
Another film that was good in the version released in theaters, but leveled up once the director got to share his preferred vision. As always, Malick films are slow and elliptical by design. There are lots of shots of rain falling, lovers running through fields, and sounds of nature. Whether it’s historically accurate or not, the film’s power cannot be overstated. Colin Farrell and Q’orianka Kilcher are simply stunning as the star-crossed John Smith and Pocahontas, with terrific supporting work from Christopher Plummer, David Thewlis, and a pre-Batman Christian Bale.
3. Brokeback Mountain (dir. Ang Lee)
The grand romantic tragedy of the 21st Century. Combining Sirkian melodrama with a deconstruction of Western myth (courtesy of an adaptation by Larry McMurtry and Diana Osanna), Brokeback Mountain may have been modern in the sense that its doomed lovers are both men, but it’s old-fashioned in all the best ways. Even more so than his Oscar-winning turn in The Dark Knight, Heath Ledger’s performance here as the closed-off Ennis is the perfect encapsulation of his gifts, gifts we were robbed of when he tragically passed away in early 2008. Just as good is Michelle Williams, as the devastated wife who doesn’t understand his repressed anger and deep dissatisfaction long before she sees him kissing another man. She should have won the Oscar. The film should have won Best Picture, too, but we don’t need to re-litigate that for the umpteenth time.
2. Memories of Murder (dir. Bong Joon-ho)
Director Bong’s exploration of a detective’s (and a country’s) reckoning with its first serial killer was a major influence on David Fincher’s Zodiac, so it’s no surprise that I loved it. Though less focused on procedure, both films share obsession as a main theme, and an intentionally unsatisfying ending. This one has more drop-kicks, though, which can’t be discounted.
1. Pride & Prejudice (dir. Joe Wright)
This is not the movie I’ve seen the most times in its entirety. But I have seen parts of this Jane Austen adaptation more than any other film, and it is highly unlikely that record will ever be broken. My ex-wife used to put this on every night to fall asleep to. While I admired it initially, this constant exposure deepened my appreciation. That’s not just nostalgia talking. The film’s beautiful score, breathtaking cinematography, and perfect costume design never lose their power. But the acting, especially from Donald Sutherland – who should have won the Oscar that year, but wasn’t nominated then or ever – make the film feel truly alive.
Honorable Mentions
The Aristocrats (dirs. Penn Jillette, Paul Provenza)
Caché (dir. Michael Haneke)
Constantine (dir. Francis Lawrence)
Howl’s Moving Castle (dir. Hayao Miyazaki)
Hustle & Flow (dir. Craig Brewer)
Jarhead (dir. Sam Mendes)
Junebug (dir. Phil Morrison)
The Matador (dir. Richard Shepard)
Match Point (dir. Woody Allen)
Mr. & Mrs. Smith (dir. Doug Liman)
Paradise Now (dir. Hany Abu-Assad)
Red Eye (dir. Wes Craven)
Sin City (dirs. Robert Rodriguez, Frank Miller)
Star Wars: Episode III – Revenge of the Sith (dir. George Lucas)
Wallace & Gromit: Curse of the Were-Rabbit (dir. Nick Park)