The Best Movies of the 2000s

When I originally made this list it was presented in a way that made it difficult to read from beginning to end, so here are reviews of the 30 best movies of the 2000s, followed by the top 50 in list form; enjoy!

#30. Frozen River (2008) 

One of the many virtues of movies is that they also act as vehicles for social commentary; Frozen River does just that. Turning in an Oscar-nominated performance, Melissa Leo stars as Ray Eddy. A single working mother struggling to support her two children. Ray works as a clerk at a local convenience store, barely making ends meet. Life becomes even more difficult when her car is stolen. When she finally tracks it down, she encounters Lila (Misty Upham) who defends steeling Ray’s car by claiming that she found the car abandoned with the keys in it. What ensues is an uneasy alliance between Ray and Lila as they address their individual financial woes by smuggling illegal aliens across the U.S./Canada border. Written and directed by Courtney Hunt, Frozen River is as much a story about the illicit smuggling of human beings as is it is a story of clashing cultures between whites in a rural upstate New York town and the residents of a nearby Native American reservation. As a winner of the Sundance Film Festival Grand Jury Prize (Dramatic), the film succeeds on the strength of the relationship between Ray and Eddy. In addition to struggling financially, Lila has her own family problems as she struggles to prove that she is responsible enough to take custody of her young daughter. In the end, Frozen River is a unfriendly reminder of how much two people from different cities and cultural backgrounds may have in common as it relates to life’s struggles.

#29.  Once[2007]: 

As a musician, I’m always intrigued by other musicians, the lives they lead, and the music that defines them.  Unfortunately,  movies about musicians don’t always work.   For every Almost Famous, there’s a Rock Star (all due respect to Jennifer Aniston and Mark Wahlberg).  As a result, I’m always leery of that genre of film.   So it was a pleasant surprise when I had occasion to watch Once. Although I had read all of the accolades, it wasn’t until my good friend Jenny Green demanded that I watch the movie that I actually did so.

The story centers around a struggling musician played by Glen Hansard who befriends fellow musician/pianist Marketa Irglova (referred to simply as “Girl”) while playing on the streets of Dublin for loose change.  The two strike up a conversation that leads to both a personal and musical relationship.  Although the romantic chemistry between the two is palpable, the movie focuses more on their relationship as musical collaborators.  In one scene Hansard and Irglova step into a music store that she often frequents where she is allowed to play the piano.  Hansard plays one of his original tunes (the Oscar-award winning song “Falling Slowly”) for Irglova and the two proceed to play it together.  In that one moment, there is more musical authenticity and emotion exhibited between the two than any other film you’re likely to see about musicians or the practice of making music, short of a documentary.  This is in part why the movie works.  Its simple, its short, and its real.

#28.  The Squid and the Whale [2005]: 

Noah Baumbach wrote and directed this quirky “dramedy” that revolves around the struggles of a family torn apart by divorce.  As the son of film critics, The Squid and the Whale, is also semi-autobiographical in that it closely parallels events in his own life.  His parents were writers/film critics that divorced during his teen years.  Appropriately, the movie is set in the 80s and the parents here- played brilliantly by Jeff Daniels and Laura Linney- are writers.

Normally a family drama about divorce would simply be just that.  Yet the humor here is undeniable.  It’s almost as if Wes Anderson did a remake of Kramer vs. Kramer (not coincidentally, the film was produced by Anderson).  There are so many random nuggets of humor interwoven with the drama.  First, there’s the 12-year old son Frank’s (played by Owen Kline) random episodes of acting out; there’s the mini tryst that unfolds when one of Daniels’ students (Ana Paquin) moves in…..oh and then there’s the other son (played by Jesse Eisenberg) who has his own exploits.  But the icing on the cake is William Baldwin who plays a quasi-intellectual hippie tennis instructor who has replaced Daniels as Linney’s new love interest.

At times the movie is almost too painful to watch, as the uncomfortable scenes are numerous.  In the end, Baumbach delivers a great movie by striking the right balance between the pain and comedy that defines the movie.  The acting is also wonderful.  Most notably Daniels, who does an excellent job as the failing father and ex-husband.

Despite being unbearable at times, The Squid and the Whale does not disappoint.

#27.  Munich [2005]: 

As one of America’s greatest storytellers, Steven Spielberg has often exercised his ability by using lesser-known stories as vehicles to explore some of the great tragedies throughout history (see Amistad and Schindler’s List).   With Munich Spielberg explores the history and nature of the middle east conflict between the Palestinians and the Israelis.  To do this, he chronicles how a covert group of Israelis retaliated against the “Black September” terrorists; the individuals  responsible for the massacre of Israeli athletes at the 1972 Munich Olympics.  Instantly, Speilberg’s deft touch comes through as he weaves actual news coverage of the massacre within the events as they unfold in the movie.  All in all, the movie is filled with suspense as the group embarks on a bloody journey to avenge the deaths of those athletes who lost their lives.  Eric Bana gives a brilliant performance as Avner, the de facto leader of the group and the protagonist.  Throughout, the internal struggle that takes place within Avner becomes more clear with the killing of each target.

Ultimately Munich conveys a message.  Indeed, Spielberg spares no expense in illustrating the difficulties of engaging in a back-and-forth war with no end, during which the purpose of the conflict gets lost.  Although it gets a little long in the tooth towards the end, the movie still deserves to stand alongside Spielberg’s other great works.

#26.  The 25th Hour [2002]:

Director Spike Lee entered into our national conscience with 1989’s Do the Right Thing.  As a movie about race-relations in the highly polarized Bedford-Stuyvesant neighborhood of Brooklyn, it remains quite possibly the most significant movie on race in at least my lifetime.  What followed were a series of gems (Malcolm X, He Got Game), and a few serious missteps.  Fortunately for Lee and everyone else that has come to enjoy his movies, he followed 2000’s woeful Bamboozled with The 25th Hour.  While Lee made his bones exploring racial issues, he steers away from the subject here.

The movie centers around Montgomery “Monty” Brogan, played by Edward Norton.  Monty has recently been sentenced to prison for 7 years and is preparing to head upstate to serve his time.  The title refers to the focus of the movie, which is Monty’s last day as a free man.  With the aid of flashbacks, the movie follows Monty’s past as well as his last day as a free man, as he spends it with his girlfriend Naturelle (Rosario Dawson), and his two best friends Jacob and Frank; played by Philip Seymour Hoffman and Barry Pepper, respectively.

Shot in the wake of the attack on the Twin Towers, The 25th Hour is as much a postcard to New York City as anything else.  But what really makes the movie work is Norton and his vulnerabilities as he slowly comes to terms with the realization that his life will soon drastically change.  In addition to Norton, there are strong performances here by Hoffman, and Ana Paquin who plays a high school student of Hoffman’s.  Playing that role in a way that only Paquin can, she creates real tension with Hoffman.

If, like me you are a fan of Lee’s work, you will be pleasantly surprised to see that his directing chops are still in tact.  You might also be disappointed that you haven’t seen more from him, as he is still one of America’s best and most important filmmakers.

#25.  Crash [2004]: 

Paul Haggis’ brilliantly filmed drama about race relations in post-911 Los Angeles was as much a slap in the face, as it was a breath of fresh air.  With strong performances by a coterie of fresh and established faces, the film did a wonderful job of questioning notions of a post-racial society.

Shot from several different perspectives, the movie examines the lives of several main characters portrayed by Don Cheadle, Terrence Howard, Brendan Fraser, Sandra Bullock, Matt Dillon, Ryan Phillippe and rapper turned actor Christopher “Ludacris” Bridges.   The film chronicles each character as inevitably their paths cross, ultimately crashing into one another.  Complexity ensues as each interaction reveals a different racial bias.

Indeed, Haggis uses a sledgehammer to get his point across.  At times the story seems far-fetched.  Yet it is effective in getting across the point that all of us, regardless of ethnicity hold preconceived notions about others based upon their cultural backgrounds.  Critics complained that the movie was an unrealistic portrayal of race relations in this country.  Although this criticism has some merit, it misses the point.  Crash is a movie that forces us to re-think the cultural lenses through which we view our fellow citizens as well as the society at large.   In conveying the message in a compelling way it strikes just the right tone.

#24.  Half Nelson [2006]:

I’ve slowly come to realize that Ryan Gosling is indeed one of the best actors in Hollywood.  Although it may seem obvious to some, it was not always clear to me.  Prior to Half Nelson, my only familiarity with Gosling was as the male lead in 2005’s touching, but drab The Notebook.  Here, Gosling establishes himself as one of the best actors of his generation.

Gosling plays Dan Dunne, a young, hip, but unorthodox high school teacher working in a tough Brooklyn school.  During the day he’s a breath of fresh hair to his young pupils as he puts forth a dynamic style of teaching, bent on real-world application.  After school he brings passion to his other job as the coach of the girl’s basketball team.   What his students and teaching peers do not know is that this is a facade.  Dan is also addicted to crack.  Clearly tormented by demons that Dan is unable to dispose of, he continues to live this double life.  Dan’s double life is exposed when one of his players, Drey (played by Shareeka Epps) catches him in the act of drug use.  What follows is a relationship that develops between the precocious Drey and Dan as they deal with unpleasant realities.

Gosling and Epps are both excellent as two people that form a unique bond over the unlikeliest of circumstance.  Gosling’s Academy Award nominated performance alone is enough reason to see this movie.  But the manner in which the story is told is quite effective.  Half Nelson draws you in, keeping you there as you try to figure out when its all going to come to a head.

#23.  Waltz with Bashir [2008]:

In many ways, Waltz with Bashir is the most unique movie I’ve seen in quite some time.  At the very least its one of the most unique movie on my list.  At first glance, it may simply appear as an animated feature but its actually a documentary.  Written and directed by Ari Folman, the film chronicles Folman’s experiences serving in the Israeli army during Israel’s war with Lebanon in 1982.

As an animated feature, the film is one to marvel.  Visually, the feel of the movie is stylish, yet provacative.  The animation style looks similar to  interpolated rotoscoping (see A Scanner Darkly) in which animation is transposed over live footage.  Filled with music from various Israeli recording artists, the score does an excellent job of underscoring each scene.

On the whole, Waltz with Bashir is a brilliant movie.  Folman uses the film quite ably as a mechanism to work through  what was obviously a trying time in his life.  Although it is an animated documentary, the closing scene in the film truly brings home the realism of Folman’s experience.

#22.  The Assassination of Jesse James by the Coward Robert Ford [2007]: 

Before I begin, I must start off by saying that this is a very long movie; as in nearly three (2:40) hours long.  That said, its a pitch perfect portrayal of one of America’s most notorious criminals, and the man that murdered him.  One more thing, my assessment of this movie may be a bit skewed.  I’m biased towards anything with Mary Louise Parker in it and I love Westerns so these two aspects give the movie an implicit bump in ratings.

Nevertheless, here we find Brad Pitt playing what many believe to be one of the most accurate portrayals of James.  One of the things I love the most about the film is that it goes to great lengths to explore the cult of personality that was Jesse James.  After all, there were no movie stars in those days.  Train robbers were about as close as you got to celebrity status.  And of course (like Britney Spears today) James had his own obsessed fans; enter in Robert Ford.  Casey Affleck — who we can all agree is a much better actor than his brother Ben — plays the role of a lifetime as the star-struck Ford.  Hell bent on becoming a member of James’ gang, he forges a friendship with James that ultimately turns sour.

What really stands out though is the cinematography.  Set during the time of reconstruction, the camera follows James as he wanders through the heartland of America depicting beautiful landscapes, dark nights, and amber waves of grain that go on as far as the eye can see.  If you don’t mind the length and you’re partial to Westerns this is a must see.

#21.  In the Bedroom [2001]: 

As I move further down my list, I still find myself being saddled with great ambivalence over where certain movies are ranked.  After all, these are all great movies (at least in my estimation), so choosing one over the other can be quite difficult, if not tedious.  I say all of this now because I’m realizing as I write this that In the Bedroom is a force as a movie.  It has all the characteristics of a great film: great writing, a great story, strong acting, and a few surprises.

In the Bedroom is a story of tragedy and subsequent grief.  Set in a small town in Maine, Matt and Ruth Fowler are a married couple, troubled by their young son Frank’s (Nick Stahl) relationship with the older Natalie (Marisa Tomei).  [Spoiler Alert] Consternation turns into something far worse when Frank is suddenly killed by Natalie’s jealous estranged husband in a bout of lover’s rage.  As this happens early on, the movie turns to the emotions that consume both Matt and Ruth (played by Tom Wilkinson and Sissy Spacek, respectively).  Both Spacek and Wilkinson are at their usual best as they struggle to deal with the rage behind the death of their son.  With this loss, Matt and Ruth are forced to look inward at each other and their relationship to find answers.

In the end, there’s a little bit of everything in this movie.  Directed wonderfully by Todd Field, In the Bedroom offers real emotion, suspense, and the type of acting you don’t get very often in a movie; a definite must see.

#20.  Gladiator [2000]: 

Fresh off of 1999’s hugely successful “The Insider,” Hollywood resident “bad boy” Russel Crowe returned with Gladiator.  By the time Gladiator was released,  Crowe had already established himself as one of the preeminent actors in Hollywood, but it was here that he became a household name.  Directed by Ridley Scott, Gladiator was both a commercial and critical success garnering a vast number of accolades, including Academy Awards for Best PictureBest Actor (Crowe).

Set during the time of Emperor Marcus Aurelius’ rule, Gladiator tells the story Maximus (Crowe), a general in Marcus Aurelius’ army who is chosen by Aurelius to be his successor as Emperor of Rome.  Commodus (played brilliantly by Joaquin Phoenix), as the son of Aurelius learns the news and needless to say, does not take it well.  In a jealous rage he murders his father, becomes Emperor of Rome and sets out to establish his power by murdering Maximus and his family.  Maximus escapes only to be captured by a slave owner.  As fate would have it, Maximus finds himself back in Rome, but as a slave-turned-hero, fighting for his life in the Colosseum as a gladiator.

In many ways, Gladiator is a modern interpretation of some of the great movies of the 1960s such as Spartacus.  Although it is loosely based on historical events, its not meant to be a history lesson.  Rather, its a story about a hero, portrayed quite ably by Crowe.  The cinematography is top notch and the casting is excellent, particularly with Phoenix playing foil to Crowe the hero.  As one of my favorite movies of any decade its a definite must-see; action movie buffs and Crowe fans alike will enjoy.

#19.  The Lord of the RingsReturn of the King [2003]: 

Any of the three parts of Peter Jackson’s adaptation of the Lord of the Rings trilogy could (and probably should) have been included on the list.  As such, this is in some ways a reference to the trilogy as a whole.  I mention Return of the King as the third and final installment in the trilogy because it is- at least in my estimation- the best of the three.  The film is the most action-packed and its the easiest to understand.

Return of the King finds Frodo Baggins (Elijah Wood) and Samwise Gamgee (Sean Astin) as they make their way to Mount Doom to destroy the One Ring that “controls them all.”  The trilogy as a whole is aided by strong performances from Viggo Mortensen who plays the King Aragorn, Ian McKellen, and Cate Blanchett.  The story line does not disappoint either as it stays largely true to J.R.R. Tolkien’s brilliant novel.

Overall, the trilogy is quite an advancement in film making.  Jackson’s use of special effects set a new standard for science fiction films.  Particularly, the use of computer generated imagery (“CGI”) to create characters such as  the sympathetic but villainous Gollum.

As far as science fiction films go, the Lord of the Rings trilogy is about an 11 on the geek scale.  Yet, it ranks up there (not quite, but close) with the Star Wars trilogy in terms of scope and ambition.

#18.  The Pianist [2002]: 

The great (and exiled) Roman Polanski directed this brilliant film, based upon  Wladyslaw Szpilman’s autobiography.  The film tells the story of how Szpilman evaded capture by the SS during Hitler’s seizure of Poland.  Adrien Brody turns in the performance of a lifetime as Szpilman.  As is the case with several movies on my list, its a historical piece so it gets an extra bump in the rankings.  Moreover, I have a particular fondness for the movie as its based on events that took place during WWII.

No doubt there have been many films based upon the plight of those that suffered during Hitler’s reign of terror.  So its not exactly easy to direct a film that takes a unique perspective on this sad part of our history.  Yet Polanski succeeds in part because it is a personal venture.  Polanski lost a mother during the holocaust and managed to flee to the countryside, thus avoiding capture as did Szpilman.  The terror that gripped Szpilman is portrayed quite ably by Brody; he even lost 29 lbs. during production of the film.  In turn, he became the youngest man ever to win an Academy Award for Best Actor.

Some may fine The Pianist a bit dull, but the desolation and despair that characterized Szpilman’s life as he hid and ran from the SS is quite palpable; for that I think its deserving of a spot on my list.

#17.  Children of Men [2006]: 

Great sci-fi films often pose novel questions about the future.  Children of Men, follows this path by asking, what would happen if the human race suddenly became infertile? Set in the United Kingdom in 2027, the film is about the discovery of the first woman to become pregnant in 18 years.  Directed and co-written by the great Alfonso Cuarón (Y Tu Mama Tambien, Harry Potter and the Prisoner of Azkaban), the film deals with how the citizens of the world become increasingly paranoid and xenophobic as the future existence of the race comes into question.  Clive Owen plays the lead role as “Theo,” the man charged with transporting the pregnant woman (Kee) to the “Human Project,” a group of scientists committed to curing the infertility epidemic.  The film is haunting, brilliantly shot, and quite suspenseful as it follows Theo and Kee as they seek safe passage.

#16.  The Dark Knight [2008]: 

Christopher Nolan’s supremely crafted superhero crime thriller earns a “distinction” on my list by the mere virtue that it is the greatest movie ever made about a comic book character.  Yes you read that correctly. The original Superman movie broke serious ground, and Tim Burton’s Batman raised the bar pretty high, shattering the misconception that a movie based upon a superhero couldn’t also be  great film.  What followed were a series of superhero themed movies (SpidermanIron Man) that were well directed, fun, and entertaining.

Still, The Dark Knight is a game changer.  Its well shot, suspenseful, and the cinematography is excellent.  Christian Bale returns as the caped crusader playing the role in such a way that Michael Keaton’s performances two-decades prior are but a distant memory; weird voice notwithstanding.  But what makes the movie shine is Heath Ledger as the Joker.  Much like Jack Nicholson did in Burton’s version, Ledger stands out as one of the great acting performances of the last decade.  Where Nicholson’s role was more comical, Ledger does the same, but is much more dark.  So much in fact that its hard to imagine how Ledger could have gone from his role in Brokeback Mountain to playing the Joker.  Anyway, comic book hero or not, The Dark Knight is top notch.

#15.  The Aviator [2004]: 

Martin Scorsese brought to life the curious but tragic story of Howard Hughes in this wonderful film.  The film follows Hughes’ life as he weaves in and out of various pursuits such as producing successful films, dating some of Hollywood’s most prominent leading ladies, and waging a war against Pan Am Airlines.  In yet another Oscar-worthy performance, Leonardo DiCaprio is brilliant if not haunting in the lead role as Hughes.  Despite Hughes’ major triumphs, he was also plagued by an obsessive-compulsive disorder.  As this disorder plays an increasingly larger role in his life through time, DiCaprio portrays Hughes’ darker days with great skill.  A coterie of other fine actors complement this film.  Most notably Cate Blanchett [as Katherine Hepburn] who won an Academy Award for Best Supporting Actress.

#14.  Mystic River [2003]: 

I could have easily placed at least three of Clint Eastwood’s movies from the past decade on my list. Indeed, Gran Torino and Million Dollar Baby are both brilliant films. But neither stacks up evenly against Mystic River, which is the best movie Eastwood has directed since 1992’s Unforgiven.  Like Eastwood’s other gems, Mystic River is harrowing, suspenseful, well acted, and well written.  The story focuses on three friends, one of whom (Dave played by Tim Robbins) is molested as a young boy.  How this experience affects Dave and his two other friends looms large on the rest of the movie.  The story then shifts to the three boys as men and how they are each affected by the murder of Jimmy’s (Sean Penn) young daughter.  Circumstances lead Jimmy to suspect that Dave may have had a role in the murder.  Sean’s role is that (Kevin Bacon) he is police detective charged with investigating the crime.  It is classic Eastwood as the movie heads toward an ending that can only be characterized as inevitable.

As a testament to the strong acting performances, both Penn and Robbins were awarded with Academy Awards for Best Actor and Best Supporting Actor, respectively.

#13.  The Lives of Others [2006]: 

Winner of the 2007 Academy Award for Best Foreign Language Film, The Lives of Others is a gripping drama about an agent of the East German secret police (Stasi) that is charged with monitoring the daily activities of a German playwright and his lover.  The film is set in 1984 at a time when East Germany was a socialist state occupied by the Soviets.  Considering the period in which the film is based, the undercurrent of communism and the fear that it brought, is quite prominent.  Yet the movie focuses more on the transformation of the agent, Captain Gerd Wiesler and how he becomes disillusioned with his role in the government.  As a lover of politics and history, I’m naturally a sucker for movies like this.  If you can appreciate how far that part of the world has come, then you’ll appreciate The Lives of Others.

#12.  Wedding Crashers [2005]: 

Of all the great comedies of the last decade, this is the one that holds up the best.  As its probably one of the most widely viewed movies of that same period, I’ll spare you on all the details.  If you haven’t seen this movie (first off shame on you), the film is about John (Owen Wilson) and Jeremy (Vince Vaughn) who play full-time mediators and seasonal wedding crashers.  Although it gets a bit long-winded towards the end (Will Ferrell cameo notwithstanding) it is one of the few movies that I will watch if its on t.v. regardless of how many times I’ve seen it.  Never before has crashing a party seemed like so much fun.  Vince Vaughn is at his absolute best – especially in the beginning of the movie as he goes on his diatribe about dating – and he and Wilson work brilliantly together.  Throw in a sprinkle of Christopher Walken and what you have is a surefire classic.

#11.  The Savages [2007]: 

This is probably the best movie you’ve never heard of.  In all honesty, I have a natural inclination to all movies staring Laura Linney so my grade may be a bit skewed but really, I don’t think so.  Linney and the brilliant Philip Seymour Hoffman play a brother and sister that are forced to set aside the awkwardness of their relationship in order to deal with their dying father.  The movie begins with the sister, Wendy (Linney) being given the news that their father has been tossed out of his retirement community digs.  As she is living under dubious circumstances herself she calls on the brother Jon (Hoffman) to help her with the father who is also suffering from dementia.  Both brother and sister have been estranged from their father.  As a result, what they’re being asked to do places a strain on both of their lives.  The reality of these familial relationships is powerful.  As their father basically ran out on them, both Wendy and Jon are saddled with the responsibility of financially and emotionally supporting a father that did neither for them.  This is a funny, quirky, awkward and sometimes difficult movie to watch but its very enjoyable, check it out.

#10.  Sideways [2004]: 

Alexander Payne’s quirky and sometimes painful “dramedy” was my favorite movie of 2004.  In addition to directing the movie, Payne won an Oscar for Best Adapted Screenplay along with Jim Taylor.  The film stars Paul Giamatti (Miles) and Thomas Haden Church (Jack) as two old friends that decide to head up to the wine country of Santa Barbara for a bachelor party.  Although Miles and Jack appear to be close friends, their lives are clearly headed in opposite directions.  While Jack is a semi-successful actor soon to be married, Miles is a teacher and failed writer that has just went through a divorce.  Despite the fact that their get-together is supposed to be a bachelor party, Miles can’t seem to shake the fact that his life is in shambles.  Giamatti, no doubt a great actor, plays the role almost too well.  In fact,  there are a few scenes where his eternally dour disposition is unbearable to watch.  Fortunately, Church is there to be the yin to Giamatti’s yang., as Church pretty much owns every scene he’s in.

Aside from great performances by Church and Giamatti, Sideways is further aided by Sandra Oh, who gets involved with Church’s character, not knowing he is soon to be married, and Virginia Madsen who plays Miles’ love interest in the movie.  Aside from an Oscar win for screenplay, Church and Madsen were nominated for supporting actor/actresses awards.

#9.  There Will Be Blood [2007]: 

I continue my top ten with Paul Thomas Anderson’s brilliantly crafted drama about a duplicitous oil prospector.  Based on Upton Sinclair’s novel “Oil,” There Will Be Blood stars Daniel Day-Lewis in yet another powerful performance as the lead character Daniel.  Driven by the endless pursuit of building wealth, Daniel goes to great lengths to build his empire.  In his pursuit, he is forced to deal with Eli, an unscrupulous preacher whose family sits atop a piece of valuable land.

Lewis is maniacal in his performance.  Naturally, he secures a second Academy Award for his performance here.  Anderson is in full command here, as the film is shot quite skillfully.  The tragedy of Anderson’s masterpiece is that it was somewhat overshadowed by the Coen Brothers’ No Country for Old Men, which was released in the same year.

#8.  The Departed [2006]:

Amazing performances shape this great crime drama.  The film is a crime drama that centers around an Irish crime boss (Jack Nicholson), his protege (Matt Damon), and Leonardo DiCaprio whose character sets out to infiltrate the crime family.  Directed by Martin Scorsese, the film is a remake of the 1992 Hong Kong film Infernal Affairs.  Despite an accomplished career as a filmmaker, The Departed earned Scorsese his first Oscar award.  Its an expertly crafted tale of crime and suspense, and the acting is first-rate.  Aside from the three most prominent characters, the film is aided by strong performances from Marin Sheen, Mark Wahlberg, and Vera Farmiga.

#7.  High Fidelity [2000]: 

For those of you that know me well, I’m sure you’ve heard me say once or twice that High Fidelity is one of my all-time favorite movies.  If you haven’t then there it is.  Which begs the question of why its not #1 on my list.  I guess my answer to that would be that I think a list of favorite movies is different from a list of great movies.  If they were, my all time favorites list would include movies like Real Genius and The Blues Brothers.  Having said all of that, High Fidelity is a great movie.  The story centers on John Cusack who plays Rob Gordon (“THE Rob Gordon”), a record store owner who falls on hard times when his main squeeze moves out.  Its your classic boy-loses girl-wants-girl-back John Cusack movie, except this time the story holds up much better and the complimentary parts are much stronger.  Most notably Jack Black who plays one of Cusack’s record store employees.  Black makes the movie and owns every scene in which he appears.  The soundtrack is great, its dynamic and the classic Stevie Wonder song “I Believe (When I Fall in Love it will Be Forever) plays over the closing credits, signifying the musical credibility of the film.  Throw in your random Lisa Bonet cameo and you have one of the greatest romantic comedies ever made.

#6.  4 Months, 3 Weeks, and 2 Days [2007]: 

Remember how I said that The Savages was the best movie you’ve never heard of?  Scratch that, this one is.  4 Months, 3 Weeks, and 2 Days is a film that is set during the late eighties during a period of communist rule in Romania.  The story follows  a female college student who becomes pregnant then decides to have an abortion.  As abortion was illegal in Romania at that time, she seeks help from her roommate in arranging an abortion through what turns out to be rather dubious means.  Needless to say, an unregulated, illegal market for abortions can no doubt lead to complications and these women face many.   The film is a foreign language film, so if you don’t mind the subtitles, I implore you to watch this powerful film.

#5.  Pan’s Labyrinth [2006]: 

Fresh off the success of Hellboy, Mexican filmmaker Guillermo del Toro returned with this haunting fairytale.  In some ways a modern day Alice in the Wonderland, the story centers on Ofelia, a young girl who meets a faun in a nearby labyrinth.  The faun (“Pan in Spanish) tells Ofelia that she must complete a series of tasks in order to bring peace to the soul of a fallen princess.  At first blush, the movie seems like a simple fairy tale but its much more complex than that.  There is a political subtext to the movie as its set in the wake of the Spanish civil war and the repressive regime that ruled.  Aside from an intriguing story, the movie is visually stunning, filled with vivid imagery, and at times its just downright scary (wait till you see the guy with no eyes).  If you’re willing to let your mind wander a bit, check out Pan’s Labyrinth.

#4.  Almost Famous [2000]:

I’ve long since been a huge fan of Cameron Crowe’s films for a variety of reasons.  Crowe’s films are typically well-written, well-acted, quirky and they all feature excellent music.  Without question, Almost Famous is the best of his illustrious career.  Almost Famous is a semi-biographical movie about fictional teenage writer William Miller who gets the ear of Rolling Stone magazine.  Impressed with his work and mistaking Miller for someone much older, the magazine hires him to do a story on the fictional band “Stillwater.”  Despite being underage, Miller embarks on a trip around the country, riding along with the band and its groupies.  Among those groupies is the lovely Penny Lane (played quite well by Kate Hudson),  with whom Miller promptly falls in love.  Miller’s adventures mirror those of Crowe, who as a teenager traveled the country writing for Rolling Stone.  Along the way Crowe interviewed some of the most influential bands of the 70s such as Led Zeppelin, the Eagles, and the Allman Brothers.  Like several other movies by Crowe, his wife and Heart lead guitarist Nancy Wilson provides a wonderful score.  The soundtrack is filled with some of the greatest songs of the last 30 years.  In sum its a great movie, tells a great story, and is just downright fun from the beginning to the end.

#3.  No Country for Old Men [2007]: 

Not since Hannibal Lecter have we seen a villain as treacherous and deadly as the sociopathic Anton Chigurh.  As the most celebrated movie in the Coen brothers (Joel and Ethan) canon, No Country for Old Men, is a thriller that revolves around a mysterious suitcase full of money, the lowly guy that found it, and the small town Texas sheriff, who sets out to find them both.  Javier Bardem plays Chigurh, Josh Brolin stars as Llewelyn Moss, the guy that finds the suitcase, and Tommie Lee Jones is the sheriff.  Based upon a novel written by Cormac McCarthy, No Country for Old Men is generally dark in tone, which is a departure from many of the Coen brothers’ other movies.  Although there are some similarities (excellent dialogue), the movie has a element of terror that is unseen in their other films.  Visually, the film brilliantly captures a vast desolation rarely seen in movies.  Tommie Lee Jones is great as the wise old sage, on his way out of the game.  Brolin turns in a strong performance of his own, establishing a relevance among other Hollywood actors previously unseen, and Bardem is simply brilliant.  As the villain, Bardem captivates, going from charismatic to terrifying in one fell swoop.  As an enormous fan of the The Big Lebowski, its hard to imagine the Coen brothers making anything better, but this one comes damn close.

#2.  Eternal Sunshine of the Spotless Mind [2004]: 

I really struggled with this one.  For several weeks I had this one as #1.  Yeah, its hard to imagine, given how many great movies I’ve chronicled, but this is truly a great movie.  From beginning to end its brilliant in all aspects.  Technically its well shot.  In particular, the dream sequences are visually striking.  The acting is top notch, as the chemistry between Jim Carrey and Kate Winslet is strong.  But what really sets the movie apart is the story.  Written by Charlie Kaufman, the Director Michel Gondry, and Pierre Bismuth, the movie is about Joel (Carrey) and Clementine (Winslet) who date each other, break up, and then decide (separately) to get the memories of the relationship erased from their collective minds.  Without spoiling the rest, I’ll simply say that they way in which the two meet and then date probably says more about relationships than perhaps any other movie I’ve ever seen.  Although they both use a method to forget each other that is clearly impossible, seeing the lengths to which both are willing to go to mitigate the emotional pain says a lot about the power of human emotion that comes from relationships.  The movie takes you on quite a ride but its funny, painful, and captivating the whole way through.

#1.  Kill Bill, Parts 1 & 2 [2003-2004]: 

As a child, I spent many afternoons beside my two brothers, glued to the television watching Kung-Fu theater.  Naturally, my appreciation for martial arts movies was cemented quite early in life.  So it was with much anticipation that I awaited the release of both installments of Kill Bill. After all, Quentin Tarantino is the greatest filmmaker of our time, so it would only make sense that Kill Bill was a masterpiece.  Well, Tarantino’s project did not disappoint.  Uma Thurman stars as the protagonist – Beatrix Kiddo, or “Black Mamba” – who embarks on a mission to settle scores with her former cohorts who together operated as a group of world class assassins.  The late David Carradine  stars as “Bill,” and is the leader of this group.  At its core, Kill Bill is a movie about revenge, but there is much more to this movie than just revenge.

What I like most about Kill Bill is that it is an homage to so many genres of film.  Most importantly, the old kung fu films of the 70s and 80s that I grew to love.  But Tarantino takes the many influences that shaped him as a filmmaker and then blends them with his own brand of filmmaking.

As is customary of Tarantino films, the story telling is out of sequence.  But what makes it all the more compelling is the scope of the characters.  Considering the lengths that Tarantino goes to develop the various characters, its no surprise that it took two movies to tell the story.  Aside from the storytelling, the dialogue is, not surprisingly, top-notch, and the action sequences are amazing.  Tarantino weaves in vivid animation sequences to give the movie even more life.  Set to a a great score by the incomparable Rza of Wu Tang fame, Tarantino goes to great lengths to tell his story.

Over time, I may grow to like this movie even more.  As it currently stands, I’d say Kill Bill is a close second to Pulp Fiction as Tarantino’s magnum opus.

And again, here is the top 50 in list order.

1. Kill Bill (2003-2004)
2. Eternal Sunshine of the Spotless Mind (2004)
3. No Country For Old Men (2007)
4. Almost Famous (2000)
5. Pan’s Labyrinth (2006)
6. 4 Months, 3 Weeks, 2 Days (2007)
7. High Fidelity (2000)
8. The Departed (2006)
9. There Will Be Blood (2007)
10. Sideways (2004)
11. The Savages (2007)
12. Wedding Crashers (2005)
13. The Lives of Others (2006)
14. Mystic River (2003)
15. The Aviator (2004)
16. The Dark Knight (2008)
17. Children of Men (2006)
18. The Pianist (2002)
19. The Lord of the Rings: Return of the King (2003)
20. Gladiator (2000)
21. In the Bedroom (2001)
22. The Assassination of Jesse James by the Coward Robert Ford (2007)
23. Waltz with Bashir (2008)
24. Half Nelson (2006)
25. Crash (2004)
26. The 25th Hour (2002)
27. Munich (2005)
28. The Squid and the Whale (2005)
29. Once (2007)
30. Frozen River (2008)
31. Zodiac (2007)
32. Lars and the Real Girl (2007)
33. L’ Enfant (2005)
34. Collateral (2004)
35. You Can Count on Me (2000)
36. Apocalypto (2006)
37. Amores Perros (2000)
38. Volver (2006)
39. Brokeback Mountain (2005)
40. Minority Report (2002)
41.  Notes on a Scandal (2006)
42.  A History of Violence (2005)
43.  21 Grams (2003
44.  The Bourne Supremacy (2004)
45.  Garden State (2004)
46.  United 93 (2006)
47.  Memento (2000)
48.  Old School (2003)
49.  The Hangover (2009)
50.  Donnie Darko (2001)

5 thoughts on “The Best Movies of the 2000s

  1. Obviously, these lists are impossible to truly get right, and everyone has their own opinions, but I want to point out some major confirmations/mishaps….

    1. Love putting Kill Bill as #1. I’d have that and No Country For Old Men as 1 & 2.

    2. Where is Sin City???? That would be top 5 for me

    3. Crash SUCKED! Maybe one of the bottom 30 movies of the 2000’s along with every Adam Sandler movie in this decade.

    4. Glad Collateral made the list. I’d have it higher, but most have forgetten about that one.

    5. Gladiator should be much higher. Yes, its popular, but you just cant fight how good it is.

    6. Wedding Crashers as the highest comedy??? Knocked Up, 40 Year Old Virgin, and several others are MUCH better.

  2. Crash in the same breath as an Adam Sandler movie? Come on man, it won an Oscar! Not that winning an Oscar is the be all, end all, but let’s not get carried away.

    Without seeing every movie on the list, it’s impossible to honestly say whether one movie’s absence from the list is an egregious omission, or truly an informed opinion. I would encourage you to do so, then think about the list.

    Gone, Baby Gone (essentially a Scorsese knock off), was entertaining, but not even in the same breath as some of the films on this list. Take a movie like “4 months, 3 weeks, and 2 days,”….I wouldn’t put Gone Baby Gone in the same conversation.

  3. WHAT!? the lord of the rings just number 19???. im sorry but thats movie should’ve been in the top 10

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