20. Punch-Drunk Love (Paul Thomas Anderson, 2002)
After making two of the best films of the 1990s, Paul Thomas Anderson shocked people by making this movie with Adam Sandler. But the gambled paid off, as the film proved that only could Sandler actually act, but also that Anderson could pull off pretty much whatever he wanted to do. The film basically deconstructs Sandler’s screen image – his character here is just as anti-social and prone to violent rages as someone like Happy Gilmore, the difference here is that Anderson and Sandler see this character for who he really is, and do not make him into some kind of misfit hero. The movie spins around and around, as Sandler gets drawn in deeper – deeper into the phone sex scam he unwittingly became a part of, deeper into his obsessive collecting of points to build up air miles, deeper into his novelty business, deeper into his dysfunctional family relationship, and finally deeper into his romance with Emily Watson, who is outwardly normal, but there is something definitely wrong with her. Philip Seymour Hoffman gives a brilliant supporting performance as the mattress king, and the films creepy soundtrack is perfect. I think if you really want to know when Anderson truly announced himself as a singular talent, it was this film.
19. Gangs of New York (Martin Scorsese, 2002)
I am better able to see the flaws in this film than I was in 2002 when I was enamored by the film. Yes, the storytelling is sloppy at times, and this is undoubtedly DiCaprio’s weakness performance in a Scorsese movie. And you could probably jettison Cameron Diaz and not lose much. I certainly understand the criticism that the film is a giant mess. But what a glorious, brilliant mess it is! There are scenes as brilliant as anything put to film before – the opening battle (in fact, the lead up to the opening battle is perhaps even better), the scene where DiCaprio wakes up to find Day-Lewis sitting there staring at him with the American flag draped over his shoulders. In fact, pretty much every scene with Day-Lewis who towers over the movie and everyone else in it, just like a character like Bill the Butcher should. The period detail, the amazing cinematography, the overall hugely ambitious, epic scope. So yeah, Gangs of New York is a flawed film. No doubt about that. But I absolutely love it just the same.
18. The Dark Knight (Christopher Nolan, 2008)
Christopher Nolan had a great decade, starting with Memento, moving onto to the underrated Insomnia then Batman Begins, then The Prestige, and finally settling on The Dark Knight – one of the great crime dramas of the decade. The key to the film is even though it is about a man who dresses up like a bat, fighting a man who dresses up like a clown, that Nolan takes the movie, and its characters seriously. Christain Bale gives a fine performance as Bruce Wayne/Batman – the best we have seen on film yet, and he is ably supported by Aaron Eckhart, Maggie Gyllenhaal and the rest of the cast. But the movie is owned by Heath Ledger who delivers a wickedly demented performance as the Joker. What the movie is really about is how do you fight an enemy with no morals or scruples – do you sink to their level, or not? That makes The Dark Knight relevant to our times and more than just a superhero movie – although it is a brilliant one of those as well.
17. The Assassination of Jesse James by the Coward Robert Ford (Andrew Dominik, 2007)
Andrew Dominik’s The Assassination of Jesse James by the Coward Robert Ford is undoubtedly the best classic western of the decade, and one of the best films the genre has ever produced. It is brilliantly shot and edited, making this look and feel like a Terence Malick at times. But it’s portrayal of Jesse James as a reluctant celebrity, who while he remains slightly crazed (it all happens in Brad Pitt’s eyes – easily his best performance), is beaten down and ready to die. Casey Affleck is the real star of the movie though as Robert Ford, a pathetic little man who idolizes James to an obsessive degree, and although he does “befriend” him, he still feels small and pathetic, which turns his adoration into a desire to kill him. The movie sticks close to the facts that we know about the case, but the film is also relevant to our times – with Affleck as almost a Mark David Chapman like character. Celebrity culture it seems is not a modern invention.
16. I’m Not There (Todd Haynes, 2007)
Bob Dylan has made himself such an enigma over the years, and has reinvented himself so many times, that a classic Hollywood style biopic would do him no justice at all. Which is why Todd Haynes’ brilliant film I’m Not There is as great as it is. Haynes uses six different actors to portray Dylan at different stages in his life, different personas if you will. You have youngest Marcus Carl Franklin as the kid who wanted to be Woody Guthrie, Christian Bale both trapped as a folk singer, and later as a gospel singer, Heath Ledger as Dylan the celebrity, Ben Whishaw as Dylan the poet, Richard Gere as Dylan the recluse and finally, in one of the very best performances of the decade, Cate Blanchatt as Dylan at the height of his fame, not knowing precisely what is expected of him, and drowning his sorrows in drug abuse. Haynes has a different style for each of his characters, influenced by different directors from Godard to Warhol to Peckinpah to Pennebaker and more. I’m Not There is a brilliant movie precisely because it doesn’t explain Dylan, who is unexplainable, but instead gives us snapshots of Dylan. Just like the song that the movie is named after says, every time we think we get a glimpse of the real Dylan, he’s gone.
15. Wall-E (Andrew Stanton, 2008)
Pixar has been one of the most consistent creative forces in America movies for well over a decade now, and Wall-E is far and away their best film. The movie is a magical silent comedy in its first act, as Wall-E, the last robot left on a deserted planet earth, continues his job of slowly cleaning up the planet destroyed by human shortsightedness. Wall-E is lonely though, so when another robot named Eve descends from the sky, he thinks he has finally found a friend. But when she is taken away on a spaceship, Wall-E refuses to let go of his friend, and travels with her back to a huge spaceship arc, which contains the remnants of humanity which have become slovenly and obese, depending on machines from everything. The film is a brilliant mixture of state of the art animation, mixed in with references to cinema’s past. As well, it is a touching love story, even though the film is about two robots. There are more magical moments in this film than in any in recent memory. Pixar has created a lot of great films in the past, but none better than this one.
14. Munich (Steven Spielberg, 2005)
It has been a very dark decade for Spielberg in his films – and none of his films were as dark, or as brilliantly conceived as Munich, his study on revenge, and the endless cycle of violence that it brings. Eric Bana heads up a team of Israeli Secret Agents, who are tasked to eliminate the people behind the planning and execution of the Munich Olympic Massacre, where a group of terrorists kidnapped and killed 11 Israeli athletes. At first Bana and his team are all for the mission – they want vengeance as much as anyone does, and they see this as their way to serve their country. But as one killing leads to another and another, and innocent people start to become involved and the mission continually expands, they all start having their doubts about the mission. Every assassination they carry out doesn’t really accomplish anything, as the terrorists simply respond in kind, and as such add more people to the list, or simply replace the man killed. Bana becomes disillusioned, and eventually leaves the mission, but becomes increasingly paranoid about his safety. In the scene that many critics point out as being the weak point of the film, or even downright stupid, Bana has sex with his wife, as we flash back to the Munich massacre – something that Bana never witnessed. But since he has lived with this moment for years – it has been the driving force behind his actions – it does make sense that he could be haunted by an event he didn’t actually witness. Far from being the naïve movie some critics have claimed – slamming the film for saying that government should never retaliate for wrongs done against them (which is just stupid), the movie instead offers a critical examination of the moral doubts that come along with taking retaliation, and more argues that a black and white policy of tit for tat vengeance leads to a kind of group insanity. Munich is the most complex film of Spielberg’s career, and one of his very best.
13. Synecdoche, New York (Charlie Kaufman, 2008)
Synecdoche, New York is a brilliant little mind fuck of a movie from Charlie Kaufman, who proves in this film that he should continue to direct his own material. The film is about a New York based theater director (Philip Seymour Hoffman), who gets a MacArthur genius grant and uses the money to stage a huge, never ending play in an abandoned factory going over the minuate of his everyday life. He rehearses the play for years, bringing in actors to play themselves, and then bringing in other actors to play the actors playing themselves, building massive life size sets, as he continues to spiral down into his own head. The world crumbles around him, but he doesn’t seem to notice. He is beset with different ailments that he cannot explain, and loses one wife after another, the whole time wishing he could have his assistant (Samantha Morton), who moved on years ago, but still remains by his side day in and day out. Synecdoche, New York is hugely ambitious – it is about nothing less than life, and we live it day in and day out.
12. A Serious Man (Joel & Ethan Coen, 2009)
The Coen brothers had a great decade – seven films, four of which appear on this top 50 list (which means that there is still one coming up). A Serious Man is both very much in line with their previous work, but also somewhat of a departure for them. In the film, Larry Gopnik (Michael Stuhlbarg) is a Physics professor in 1967 Minnesota who is being tested by God very much like Job was. His wife is cheating on him with his new age spouting friend, his tenure is at risk, his kids don’t respect him, he is drawn to the shiksa goddess next door and his brother is an absolute mess. He reaches out to three different rabbis, but finds no help from them. He struggles to do the right thing at every turn, to stay on the good path with no guidance from anyone, not even God, and when at long last he fails, he may have triggered the apocalypse. To those who say that the Coens are being anti-Semitic here, I would say that there is a big difference between being anti-rabbinical and anti-Semitic, and that even if Larry is a bit of a nebbish nerd, the Coens show tremendous sympathy towards him – much more than perhaps any other character in their oeuvre. Finally, I know some think that this is just the Coens playing God, and fucking with Larry (like say Scorsese in After Hours), but I disagree there as well. They have God play God in this film, who although he isn’t answering Larry, is still very much a part of the movie (hence the finale). A Serious Man is the Coens pushing themselves farther than they ever have before, and the result is one of their masterpieces.
11. Kill Bill (Quentin Tarantino, 2003/2004)
The two halves of Quentin Tarantino’s epic are very different from one another. Volume I is very much a breathless action movie, where The Bride (Uma Thurman) wakes up from five years in a coma and goes after the people responsible for putting her there. She storms into the first house, with Vivica A. Fox, and gets her vengeance quickly, making Fox leave behind a daughter (which could set up Volume III if Tarantino is to be believed). Then she flies to Japan and in the most remarkable, sustained action set piece of the decade fights off the Crazy 88 before confronting Lucy Liu, the one she wanted all along. The first volume moves at an almost impossibly fast pace, mixing together animation and other video formats, and coming to a conclusion that is breathtaking. Volume II is a slower, more subdued film – more typical of Tarantino as he allows his characters much more time to talk, reveling in the words they speak. I’m not sure which half of the film is better – both I think are incomplete without the other. To some, Kill Bill is Tarantino’s ultimate masturbation project – simply getting off by doing everything he ever wanted to do in a movie. But to me, Tarantino is an original talent – he takes what has come before him, mixes it all together and comes out with something completely new.
After making two of the best films of the 1990s, Paul Thomas Anderson shocked people by making this movie with Adam Sandler. But the gambled paid off, as the film proved that only could Sandler actually act, but also that Anderson could pull off pretty much whatever he wanted to do. The film basically deconstructs Sandler’s screen image – his character here is just as anti-social and prone to violent rages as someone like Happy Gilmore, the difference here is that Anderson and Sandler see this character for who he really is, and do not make him into some kind of misfit hero. The movie spins around and around, as Sandler gets drawn in deeper – deeper into the phone sex scam he unwittingly became a part of, deeper into his obsessive collecting of points to build up air miles, deeper into his novelty business, deeper into his dysfunctional family relationship, and finally deeper into his romance with Emily Watson, who is outwardly normal, but there is something definitely wrong with her. Philip Seymour Hoffman gives a brilliant supporting performance as the mattress king, and the films creepy soundtrack is perfect. I think if you really want to know when Anderson truly announced himself as a singular talent, it was this film.19. Gangs of New York (Martin Scorsese, 2002)
I am better able to see the flaws in this film than I was in 2002 when I was enamored by the film. Yes, the storytelling is sloppy at times, and this is undoubtedly DiCaprio’s weakness performance in a Scorsese movie. And you could probably jettison Cameron Diaz and not lose much. I certainly understand the criticism that the film is a giant mess. But what a glorious, brilliant mess it is! There are scenes as brilliant as anything put to film before – the opening battle (in fact, the lead up to the opening battle is perhaps even better), the scene where DiCaprio wakes up to find Day-Lewis sitting there staring at him with the American flag draped over his shoulders. In fact, pretty much every scene with Day-Lewis who towers over the movie and everyone else in it, just like a character like Bill the Butcher should. The period detail, the amazing cinematography, the overall hugely ambitious, epic scope. So yeah, Gangs of New York is a flawed film. No doubt about that. But I absolutely love it just the same.18. The Dark Knight (Christopher Nolan, 2008)
Christopher Nolan had a great decade, starting with Memento, moving onto to the underrated Insomnia then Batman Begins, then The Prestige, and finally settling on The Dark Knight – one of the great crime dramas of the decade. The key to the film is even though it is about a man who dresses up like a bat, fighting a man who dresses up like a clown, that Nolan takes the movie, and its characters seriously. Christain Bale gives a fine performance as Bruce Wayne/Batman – the best we have seen on film yet, and he is ably supported by Aaron Eckhart, Maggie Gyllenhaal and the rest of the cast. But the movie is owned by Heath Ledger who delivers a wickedly demented performance as the Joker. What the movie is really about is how do you fight an enemy with no morals or scruples – do you sink to their level, or not? That makes The Dark Knight relevant to our times and more than just a superhero movie – although it is a brilliant one of those as well.17. The Assassination of Jesse James by the Coward Robert Ford (Andrew Dominik, 2007)
Andrew Dominik’s The Assassination of Jesse James by the Coward Robert Ford is undoubtedly the best classic western of the decade, and one of the best films the genre has ever produced. It is brilliantly shot and edited, making this look and feel like a Terence Malick at times. But it’s portrayal of Jesse James as a reluctant celebrity, who while he remains slightly crazed (it all happens in Brad Pitt’s eyes – easily his best performance), is beaten down and ready to die. Casey Affleck is the real star of the movie though as Robert Ford, a pathetic little man who idolizes James to an obsessive degree, and although he does “befriend” him, he still feels small and pathetic, which turns his adoration into a desire to kill him. The movie sticks close to the facts that we know about the case, but the film is also relevant to our times – with Affleck as almost a Mark David Chapman like character. Celebrity culture it seems is not a modern invention.16. I’m Not There (Todd Haynes, 2007)
Bob Dylan has made himself such an enigma over the years, and has reinvented himself so many times, that a classic Hollywood style biopic would do him no justice at all. Which is why Todd Haynes’ brilliant film I’m Not There is as great as it is. Haynes uses six different actors to portray Dylan at different stages in his life, different personas if you will. You have youngest Marcus Carl Franklin as the kid who wanted to be Woody Guthrie, Christian Bale both trapped as a folk singer, and later as a gospel singer, Heath Ledger as Dylan the celebrity, Ben Whishaw as Dylan the poet, Richard Gere as Dylan the recluse and finally, in one of the very best performances of the decade, Cate Blanchatt as Dylan at the height of his fame, not knowing precisely what is expected of him, and drowning his sorrows in drug abuse. Haynes has a different style for each of his characters, influenced by different directors from Godard to Warhol to Peckinpah to Pennebaker and more. I’m Not There is a brilliant movie precisely because it doesn’t explain Dylan, who is unexplainable, but instead gives us snapshots of Dylan. Just like the song that the movie is named after says, every time we think we get a glimpse of the real Dylan, he’s gone.15. Wall-E (Andrew Stanton, 2008)
Pixar has been one of the most consistent creative forces in America movies for well over a decade now, and Wall-E is far and away their best film. The movie is a magical silent comedy in its first act, as Wall-E, the last robot left on a deserted planet earth, continues his job of slowly cleaning up the planet destroyed by human shortsightedness. Wall-E is lonely though, so when another robot named Eve descends from the sky, he thinks he has finally found a friend. But when she is taken away on a spaceship, Wall-E refuses to let go of his friend, and travels with her back to a huge spaceship arc, which contains the remnants of humanity which have become slovenly and obese, depending on machines from everything. The film is a brilliant mixture of state of the art animation, mixed in with references to cinema’s past. As well, it is a touching love story, even though the film is about two robots. There are more magical moments in this film than in any in recent memory. Pixar has created a lot of great films in the past, but none better than this one.14. Munich (Steven Spielberg, 2005)
It has been a very dark decade for Spielberg in his films – and none of his films were as dark, or as brilliantly conceived as Munich, his study on revenge, and the endless cycle of violence that it brings. Eric Bana heads up a team of Israeli Secret Agents, who are tasked to eliminate the people behind the planning and execution of the Munich Olympic Massacre, where a group of terrorists kidnapped and killed 11 Israeli athletes. At first Bana and his team are all for the mission – they want vengeance as much as anyone does, and they see this as their way to serve their country. But as one killing leads to another and another, and innocent people start to become involved and the mission continually expands, they all start having their doubts about the mission. Every assassination they carry out doesn’t really accomplish anything, as the terrorists simply respond in kind, and as such add more people to the list, or simply replace the man killed. Bana becomes disillusioned, and eventually leaves the mission, but becomes increasingly paranoid about his safety. In the scene that many critics point out as being the weak point of the film, or even downright stupid, Bana has sex with his wife, as we flash back to the Munich massacre – something that Bana never witnessed. But since he has lived with this moment for years – it has been the driving force behind his actions – it does make sense that he could be haunted by an event he didn’t actually witness. Far from being the naïve movie some critics have claimed – slamming the film for saying that government should never retaliate for wrongs done against them (which is just stupid), the movie instead offers a critical examination of the moral doubts that come along with taking retaliation, and more argues that a black and white policy of tit for tat vengeance leads to a kind of group insanity. Munich is the most complex film of Spielberg’s career, and one of his very best.13. Synecdoche, New York (Charlie Kaufman, 2008)
Synecdoche, New York is a brilliant little mind fuck of a movie from Charlie Kaufman, who proves in this film that he should continue to direct his own material. The film is about a New York based theater director (Philip Seymour Hoffman), who gets a MacArthur genius grant and uses the money to stage a huge, never ending play in an abandoned factory going over the minuate of his everyday life. He rehearses the play for years, bringing in actors to play themselves, and then bringing in other actors to play the actors playing themselves, building massive life size sets, as he continues to spiral down into his own head. The world crumbles around him, but he doesn’t seem to notice. He is beset with different ailments that he cannot explain, and loses one wife after another, the whole time wishing he could have his assistant (Samantha Morton), who moved on years ago, but still remains by his side day in and day out. Synecdoche, New York is hugely ambitious – it is about nothing less than life, and we live it day in and day out.12. A Serious Man (Joel & Ethan Coen, 2009)
The Coen brothers had a great decade – seven films, four of which appear on this top 50 list (which means that there is still one coming up). A Serious Man is both very much in line with their previous work, but also somewhat of a departure for them. In the film, Larry Gopnik (Michael Stuhlbarg) is a Physics professor in 1967 Minnesota who is being tested by God very much like Job was. His wife is cheating on him with his new age spouting friend, his tenure is at risk, his kids don’t respect him, he is drawn to the shiksa goddess next door and his brother is an absolute mess. He reaches out to three different rabbis, but finds no help from them. He struggles to do the right thing at every turn, to stay on the good path with no guidance from anyone, not even God, and when at long last he fails, he may have triggered the apocalypse. To those who say that the Coens are being anti-Semitic here, I would say that there is a big difference between being anti-rabbinical and anti-Semitic, and that even if Larry is a bit of a nebbish nerd, the Coens show tremendous sympathy towards him – much more than perhaps any other character in their oeuvre. Finally, I know some think that this is just the Coens playing God, and fucking with Larry (like say Scorsese in After Hours), but I disagree there as well. They have God play God in this film, who although he isn’t answering Larry, is still very much a part of the movie (hence the finale). A Serious Man is the Coens pushing themselves farther than they ever have before, and the result is one of their masterpieces.11. Kill Bill (Quentin Tarantino, 2003/2004)
The two halves of Quentin Tarantino’s epic are very different from one another. Volume I is very much a breathless action movie, where The Bride (Uma Thurman) wakes up from five years in a coma and goes after the people responsible for putting her there. She storms into the first house, with Vivica A. Fox, and gets her vengeance quickly, making Fox leave behind a daughter (which could set up Volume III if Tarantino is to be believed). Then she flies to Japan and in the most remarkable, sustained action set piece of the decade fights off the Crazy 88 before confronting Lucy Liu, the one she wanted all along. The first volume moves at an almost impossibly fast pace, mixing together animation and other video formats, and coming to a conclusion that is breathtaking. Volume II is a slower, more subdued film – more typical of Tarantino as he allows his characters much more time to talk, reveling in the words they speak. I’m not sure which half of the film is better – both I think are incomplete without the other. To some, Kill Bill is Tarantino’s ultimate masturbation project – simply getting off by doing everything he ever wanted to do in a movie. But to me, Tarantino is an original talent – he takes what has come before him, mixes it all together and comes out with something completely new. 
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