62. Sideways (Alexander Payne, 2004)
That rare comedy that earned a Best Picture nomination, Sideways is the story of a wine afficianado (Paul Giamatti) and his friend (Thomas Haden Church) who go on a trip that changes their lives. The film avoids asking easy questions, or providing easy answers, instead presenting us with a damaged man, and the damaged woman he falls in love with. Wine country provides a beautiful backdrop for a film that is capable of being intimate and quiet one moment, and having a naked chase scene the next. Unfortunately, it also inspired an entire generation of pretentious wine snobs. But oh well. It was worth it.
61. Munich (Stephen Spielberg, 2005)
Believe it or not, Munich is only the second-best ‘Group of badass jews get revenge’ movie on this list, but it’s still really really good. Stripped of much of the Spielberg sentimentality, Munich is an often-brutal look at an elite squad of Jewish agents striking back for the incident at the 1972 Munich olympics, where several Israeli athletes were killed.
What makes Munich such a great film is that it strikes a balance between drama, suspense/action, and historical fiction. While it never loses sight of the weight of the events contained within, it still manages to be suspenseful and fun, while also breaking your heart. It goes on about 20 minutes longer than it should, but finds a great final shot.
64. Kiss Kiss Bang Bang (Shane Black, 2005)
For a time, Robert Downey Jr. dropped off the face of the earth (with good reason). This was the first film that I remember seeing him in after his comeback, and boy is he great in it. Playing a thief pretending to be an actor training to be a detective, he gets paired up with Gay Perry (Val Kilmer) a gay private eye, who is forced to help him out when he gets involved in an actual murder plot. With an extremely dark (and often very meta) sense of humor, and a uniquely noir sensibility, Kiss Kiss Bang Bang is a remarkably fun, innately quotable film.
63. Casino Royale (Martin Campbell, 2006)
Relaunching the Bond franchise must have been a scary thing, but Martin Campbell and Daniel Craig pulled it off with Casino Royale. By showing us Bond before he was the Bond we knew, we got a fascinating look at a character who had previously remained an enigma. Why is Bond a womanizer? Now we know. Stripping away the gadgets and spy gimmickry to tell the tale of an early mission gone wrong was brilliant, and it doesn’t hurt that Daniel Craig is the best bond yet. That’s right, I said it. Too bad about that crappy sequel, though.
66. Requiem for a Dream (Darren Aaronofsky, 2000)
I’ve only seen Requiem for a Dream one time, and I’m not sure I’m ever going to watch it again. That’s how much power there is in this film, a devastating look at drug addiction that easily could have played like an afterschool special, but avoids that trap due to deft direction from Darren Aaronofsky.
Ellen Burstyn gives an incredible oscar nominated performance as a woman who loses touch with reality when she gets addicted to diet pills, as her son and his best friend and girlfriend sink deeper and deeper into heroin addiction. It’s not very cheerful.
65. Love Actually (Richard Curtis, 2003)
A collage film, Love Actually capably juggles a large number of stories about love on and around Christmas, while somehow managing to avoid become the sappiest movie you’ve ever seen. This is in part due to it’s sense of humor about itself, but also the earnestness with which it tackles it’s subject. Rather than feeling like a money-grabbing, manipulative Hollywood ‘love’ story, Curtis really seems to believe in his subject matter, and highlights this by showing that love doesn’t always work out. Bill Nighy steals the movie as an aging rockstar who finds no comfort in his debauched lifestyle.
68. Garden State (Zach Braff, 2004)
While Garden State has experienced some backlash since it came out, to me it remains a poignant, sweet, oddly funny look at one man’s awakening. It’s got an odd sense of humor, several surreal moments, and Natalie Portman as a classic Manic Pixie Dreamgirl, but somehow it never loses it’s message amongst these things. I saw Garden State at a point in my life where I was going through very similar things to the protagonist, and it really spoke to me. While I’m not sure it holds up as well as some others on this list, I think it’s a film of real power. Also, Natalie Portman is, like, WAY cute in it.
67. Monsters Inc. (Pete Docter, 2001)
One of many Pixar films on this list, because those guys just know how to tell stories, man. Monsters Inc. creates a vibrant, lived-in world of monsters, and beautifully compares and contrasts it to our own. A fast-paced madcap ride that leads to one of my favorite chase sequences ever, Monster Inc. never slows down or lets up, remaining compulsively watchable for the duration of it’s running time.
Wow, you’re still reading, huh? Alright here we go, we're almost at the halfway point! Let's continue on with numbers 70 – 61.
Get caught up:
- Top 100 Movies of the 2000s: 100 – 91
- Top 100 Movies of the 2000s: 90 – 81
- Top 100 Movies of the 2000s: 80 – 71
70. The Descent (Neil Marshall, 2006)
One of my favorite horror films of all time, The Descent follows a group of six female best friends on a terrifying, claustrophobic spelunking adventure fraught with cave-ins, in-fighting, and of course, monsters. Lots and lots of monsters. By opting not to use any CGI, but to have the monsters played by talented body actors in fantastic make-up, the film takes on an eerie realness as our lovely protagonists must fight their way back to the surface. By lulling us into a false sense of security in the relatively monster-free first half of the movie, we are unprepared for the absolute onslaught of the second half. And it is awesome.
69. 500 Days of Summer (Mark Webb, 2009)
I swear I’m not just putting this on the list because it has factored in to several very successful first dates. In fact, it’s kind of weird that it has, since as the movie is quick to point out, this is NOT a love story. Well, it is, but only for one person. The tale of a boy’s 500 day infatuation with a girl named Summer (played by my future wife, Zooey Deschanel), 500 Days of Summer has a razor-sharp script that is in turns funny and heartbreaking, whimsical and tragically down-to-earth. You’ll fall in love with Summer, just like our protagonist. And then she’ll break your heart, just like she does his.