40. The Bourne Identity (2002)
It’s hard to imagine, but there was a time when no one believed Matt Damon could play an action star. I was young enough when this film came out that I had no idea that the pretty-faced Will Hunting was an off-the-wall choice for Jason Bourne, the amnesiac assassin with deadly skills. However, I wasn’t the only audience member sucked into Doug Liman’s jittery, paranoid spy world. Two sequels by Paul Greengrass would rake up more cash and literally invent the shaky-cam fight scene, but it all starts here.
How to drive:
39. Fantastic Mr. Fox (2009)
I’ve only seen this film once, but it was such a delight that it made it past the 50 film mark with room to spare. The triple marriage of Wes Anderson, stop motion, and Roald Dahl source material sounds too good to be true. Anderson’s twee aesthetic brings Dahl’s dark quirk to life with his trademark balance of sentimentality and seriousness. Foxes vs. farmers has never been so fun.
Double Feature: Chicken Run
38. Tropic Thunder (2008)
When I saw this film in theatres, I desperately had to pee, but I was loathe to leave for a single second. The comedic gold was apparent from the ballsy “fake” trailers before the movie through the credits. Indeed, this is a film buffs’ comedy. Not only does it spoof the drama behind war films by dropping the ill-prepared actors into a real warzone, it skewers movie studios, managers, directors, and just about everyone else along the way. Stiller wrangles an amazing cast including great cameos (Tom Cruise, Nick Nolte, Matthew McConnaughey), relative new comers (Danny McBride, Jay Baruchel, Brandon T. Jackson) and classic comedians (Jack Black, Bill Hader, Steve Coogan, Robert Downey Jr.).
Robert Downey Jr. was nominated for an Oscar for his portrayal of an actor who undergoes “pigmentation” procedure to play a black guy. Yep. Black face nomination.
37. Donnie Darko (2001)
There are movies that you re-watch to re-experience your enjoyment and others that you re-watch to better understand. This falls into the latter category. Donnie Darko has a lot of ideas on physics, time travel, morals, karma – you name it. Like Fight Club before it, the film feels different on second viewing when you technically understand the order of events better and try to wrap your head around the Doomsday goings-on. It’s tough to explain what exactly makes it good, but equally hard to shake the itch you get from watching it.
36. Love, Actually (2003)
Anthology films are hit and miss, but the tight editing, sure-handed direction, and superstar cast elevate his Christmas based romance to a higher ground. Rather than tell one story at a time, we get them all at once. The “Cloud Atlas” approach pays off and allows you to watch Martin Freeman fall in love on an adult film set and Hans Gruber, er, Alan Rickman, cheat on his wife. Considered schmaltzy by some, it does feature a few romances that don’t entirely pan out (the aforementioned adultery is no fun) which gives it some real cred.
Drink…eggnog, no matter when you watch it.
35. X2: X Men United (2003)
X2 boasts a whopper ensemble cast just like Love, Actually. Although Logan/Wolverine takes the nominal center, between Rogue, Nightcrawler and – who am I kidding this movie has everyone. Much better than in X-Men: Days of Future Past, Bryan Singer cross cuts between these various mutants while also creating an urgent, coherent story. In X2, baddie William Stryker has such a powerful mutant on his side that both the X-Men and Magneto need to team up to stop him. It’s a simple but effective idea for a superhero sequel. Many people speculated that had Heath Ledger not died, there may have been a similar arrangement in The Dark Knight Rises. Most recently, Thor 2 adopted the idea, but X2 does it best.
34. Mean Girls (2004)
How to even quantify the insane influence of this film? It’s beloved by both film critics and audiences alike, and rightly so. Tina Fey’s snark has never been so sharp, Lindsey Lohan was at the top of her game, and the supporting cast kills. The only unfortunate aspect regarding the film (other than Lohan’s subsequent meltdown) is that there are too few films like it. Hollywood has been chasing the magic ever since.
33. Spider-Man (2002)
Spider-Man was the first film to break $100 million dollars in one weekend. Wow! In retrospect, we can talk a lot about the mood of America post 9/11 and a bunch of other circumstantial stuff as a reason, but the fact remains that Spider-Man is a well-made superhero origin story told by an auteur director. Nowadays the term “origin story” causes headaches, but at the time, it was an elegant way to bring the wall-crawling, web-slinger to life. The scientist turned villain plotline has been cannibalized admittedly, but Willem Dafoe nails it here. And who doesn’t love Danny Elfman’s score? Who doesn’t love the upside-down kiss? Who doesn’t love rhetorical questions?
Remember…Sam Raimi scaring young children. “Back to formula!”
32. Pirates of the Caribbean (2003)
Theme park movies don’t come any better than this. Although the idea that ghost pirates are trying to end their curse, but get foiled by the world’s foggiest, sea captain and his two green friends kinda comes from the ride, the film sails far into original territory. Honestly, while it’s been parodied and sequeled to oblivion, when you consider how swashbuckling and nuts the first movie is, you realize it’s a cinematic gem. I can’t wait to show this to a kid one day.
Remember when I told you that RDJ earned an Oscar nom for Tropic Thunder? So did Johnny Depp for Pirates.
31. In Bruges (2008)
One part witty, two parts dark, this existential hit man film isn’t for everyone. It stars Colin Farrell in top form along with Brendan Gleeson and Ralph Fiennes. It’s a vacation film about two hit men hiding out in Bruges, Belgium, and coming to terms with their terrible professional. It’s also one of the best film debuts ever, as Martin McDonaugh makes the switch from stage to screen with aplomb.
Watch with…not your parents or a first date. Repeat: not a date movie.
The Facts: Two Oscar nominations for comedic roles ain’t bad.
30. Panic Room (2002)
The bang-up team of David Fincher and David Koepp came to together to make a sharp Hitchcockian thriller about a single mom and her daughter hiding from thieves in their panic room, while the thieves work to get the loot trapped with them inside. The film capitalizes on Fincher’s style, Koepp’s pacing, and Jodie Foster’s steely performance. While some people might be turned off by its clocklike precision, I’m too busy gripping my pillow to care.
Fun fact: The opening credits are an homage to North by Northwest by Alfred Hitchcock.
29. The Incredibles (2004)
The Incredibles holds the record for most watched movie in a minivan*. It remains a pinnacle of what Pixar can do: great characters, great set-pieces, and great heart. Long before The Avengers, The Incredibles showed us what a superhero team should look like, and it’s a family film to boot. Honestly, I don’t care if The Incredibles 2 ever happens because the original is a gem.
*While I can’t actually prove this, you know it’s true. Everyone had this on constant rotation in their Honda Odyssey back in the day**.
**It was also played in a lot of Spanish classes. OK, I’ll stop with the asterisks.
28. School of Rock (2003)
Jack Black has had a surprising presence on this list. Interesting, given that I wouldn’t call him one of my favorite actors and also that his output has dropped off considerably in the current decade. Seems like his heyday really was the 2000s. Anyway, in perhaps his most iconic role, Richard Linklater directs him as a zany, guitar playing substitute who turns his class into a world class band. This film, along with the Guitar Hero video games, is hugely responsible for developing my music tastes, so I owe it that debt. It’s also one of those magical “all ages” films, made even more impressive that it doesn’t have the Pixar label on it. Seriously, check this out if you haven’t in a while.
27. Zoolander (2001)
The Zoolander II (or is it 2oolander?) teaser has just been released after years of swimming in the pit of “development.” What a great time to revisit the original story of a male model caught in a plot to assassinate the prime minister of Malaysia. Stiller gives an all-time performance here, mocking the facial and postural contortions expected by models. He’s never been as effortlessly limber as Jim Carrey, but in a similar way to Tom Cruise (one of his most famous impersonations, natch) his clear effort is part of his showmanship. Let’ s hope that an older Stiller is still game.
Fun article on the legacy of the film: www.forbes.com/sites/scottmendelson/2015/08/03/why-zoolander-2-trailer-was-a-perfect-surprise-for-mission-impossible-fans/
26. 3:10 to Yuma (2007)
There aren’t many remakes on this list, for reasons you might expect. They don’t work. 3:10 to Yuma transcend rule because it capitalizes on relaxed censorship codes to portray truly memorable menace in its villain. Furthermore, Christian Bale and Russell Crowe are excellently cast as the desperate farmer and ruthless bandit, respectively. The movie examines the nature of manhood, and what a man is willing to do when their back is against a wall. Director James Mangold shoots Monument Valley in reverence and excitement, but stays true to the story to craft a surprisingly timeless film.
25. Kiss Kiss, Bang Bang (2005)
Robert Downey Jr. earned his second chance at stardom with this razor-sharp mystery by Shane Black. He plays a thief who pretends to be a detective and teams up with an on-point Val Kilmer to solve a big LA noir scenario. It’s all hogwash, but not pure hogwash – the hardcore violence and Shane Black’s black humor carry this film onto a far more memorable plane.
24. Walk Hard: The Dewey Cox Story (2007)
I suppose it’s only natural that when John C. Reilly – the ultimate supporting man – got his chance at stardom, the film flopped. Luckily, the pitiful box office performance of Walk Hard has little connection to its quality. The film succeeds as a riotous spoof of music biopics, and is a pretty good musical in its own right. Reilly imbues the titular character with his trademark dopiness which holds the film together through its frequent shifts in historical period and tone.
Eat your heart out Johnny Cash:
23. Unbreakable (2000)
The years have not been kind to ole M. Night Shyamalan, but they have been kind to this film. It’s currently regarded as a classic of the superhero genre, and one far different than the glut of films that succeeded it. Starring Bruce Willis as the hero and Samuel L. Jackson in an iconic villain role (even better than in this year’s Kingsmen), Unbreakable seriously examines the consequences of a super hero of an average joe’s life. With none the stolid nature of his later works, Unbreakable is a textbook example of control: the production design, color palette, and sound design conform to a singular, exciting vision. This film is a gem.
22. Memento (2000)
If Following was an indication that Christopher Nolan was a promising filmmaker, Memento was the proof. The backwards/forwards time structure seems like a gimick now, but the core of the film is its weary humor. The implications of the identity crisis are so heavy, they can only be considered with a dash of chuckles. Memento is simultaneously Nolan’s most disturbing movie – the denouement merely enforces the darkest fears of the protagonist – and also his funniest. That trick makes it an instant and eternal classic.
21. Catch Me If You Can (2002)
When it comes to his New Hollywood peers (Lucas, Coppola, Friedkin, Scorsese, etc.), Spielberg arguably had the most successful period in the 2000s. His brand of thoughtful entertainment is no better on display than in Catch Me If You Can, the tale of a real life conman named Frank Abagnale Jr.who stunned the FBI for years posing as doctors, airline pilots, and more. In Leonardo DiCaprio, Spielberg found an actor capable of pulling off the charm for the role, while also conveying the loneliness of such a life on the run.