The 30 Most Underappreciated American Movies of The 21st Century So Far

underrated 2000s movies

The twenty first century has seen movies become progressively less important to popular American culture with every passing year. More films have been made in the last fifteen years than even the most thorough film buff would ever have time to see in one lifetime.

The ones that did get noticed would often be forgotten within a year of their release. Only a select few films have shelf lives of popularity, discussion, and examination, anymore and the ones that receive this attention are, sadly, often the ones that need or deserve it the least.

Many of the films made in the twenty first century from both established and unknown filmmakers don’t have a fighting chance or time to build momentum anymore. If a film doesn’t grab the public’s attention right away and have everything it has to say spelled out for them in one viewing, it is written off and it dies almost immediately.

Most the films on this list have had their widest release on home video (DVD at the beginning on the century, VOD where we are now, and time will tell what the future will bring). While the stigma of low quality attached to “straight-to-video” releases still exists, it has lessened more and more as film lovers are now understanding that home video is the modern and only remaining art house theatre.

The films that take the biggest chances, that don’t fit into molds, and that don’t revolve around super heroes are primarily to be found (and have their most lucrative life) on video. And there are many of these films, which is why it is so easy for the greatest (and often most challenging) ones to fall between the cracks.

The following thirty films on this list are all films that are lesser-known and lost on larger modern audiences to different degrees. The one link they all share is that they are intelligent, challenging, and they all never quite had the moments in the sun they deserved. These are just a few of the titles that deserve mention, as there are many more out there needing similar lists to help them get the respect and attention they need.


30. The Amateurs (2005)

The Amateurs (2005)

One of many of production company Think Film’s smaller-scaled, character–driven productions that had a solid DVD release in the mid-2000’s. The Amateurs is a very intelligent, surprisingly earnest comedy about a group of bored, middle aged suburban men who decide to invest in and produce a pornographic film.

Jeff Bridges, Ted Danson, Tim Blake Nelson, Joe Pantoliano, John Hawkes and William Fichtner are all outstanding members of the perfectly assembled ensemble cast. Bridges, as usual, stands out as the well-intentioned dreamer/ringleader behind the whole insane idea. Rich in character and humorous situations that never lower themselves to sitcom hijinks, The Amateurs wisely skips cheap laughs for intelligent, real, and human comedy.


29. Death Sentence (2007)

Death Sentence (2007)

Furious Seven hitmaker James Wan directed this revenge thriller starring an always reliable and invisibly great Kevin Bacon. The startling results went primarily unnoticed and poorly reviewed upon the film’s initial release.

Bacon stars as a loving father who loses his eldest teenage son in a gang initiation attack. Unable to move forward, he works outside of the law and exacts his own brand of violent justice. His actions soon bring revenge-seekers of their own, however, and he puts himself and the surviving members of his family through even more pain as a result.

Harrowing, relentless, and uncompromising, Death Sentence is as thrilling and intense as it is meditative on the never-ending cycle of violence that the act of revenge produces.


28. The Million Dollar Hotel (2000)

The Million Dollar Hotel (2000)

Wim Wenders’ eccentric romantic drama/murder mystery was written off at the time of its release as a vanity project for U2 front man Bono. Since it was co-written, co-produced, and features a number of different songs sung by the man himself on the soundtrack, you have to admit that it kinda sorta is a little bit just that.

However, it is also a very mesmerizing and well-performed story about an FBI agent (a completely out of his element and fun Mel Gibson) who has to weed through the impoverished and mentally ill/challenged residents of a run-down hotel while investigating a high-profile murder. Quirkball Jeremy Davies gives a typically bent but always watchable performance. He plays a mentally slow hotel resident (or squatter, to be more accurate) who quite possibly knows more than he is willing to let Gibson in on.

Surreal and moody, The Million Dollar Hotel unfolds at a languid and entrancing pace. Its atmosphere and its characters are memorable, and the film that hosts them is a uniquely beautiful, though somewhat imperfect, piece of forgotten work by a great director.


27. The TV Set (2006)

The TV Set (2006)

Another solid ThinkFilm release. Jake Kasdan wrote and directed this small-scale production about a television writer/show runner (a very humbled David Duchovny) who watches his dream project (and integrity) crumble as his beloved pilot is brought to fruition and produced by a major television network.

The TV Set is an excellent satire about the entertainment industry and the artistic dangers of compromise. Sigourney Weaver steals the show as the seemingly soul-less and slightly demented network head.


26. Solitary Man (2009)

Solitary Man (2009)

Vastly unknown and underrated film starring Michael Douglas as an aging womanizer who receives news he may have serious heart problems. His life soon collapses as the many consequences to his many bad decisions all seem to catch up to him at once.

A Solitary Man is the kind of mature, simple, and character-oriented film we are always quick to say isn’t being made anymore. You also get to watch Douglas share the screen with Danny DeVito for the first time since 1989’s War Of The Roses, which is a rather great and retrospective sight to see.


25. Ink (2009)

Ink (2009)

Independent film has changed drastically over the years. Digital technology has become so affordable and readily available that it actually is possible to take on ideas of a larger scope on a very limited, truly independent scale. Ink, a creative and highly involving modern-day fantasy is proof of just that.

The mysterious titular character, Ink (a creature who lives in the dream world of the film) steals the soul of a young girl in reality to entice a group of creatures (who also create nightmares) into a mysterious arrangement.

Like all great fantasy, Ink manages to create a moving and memorable story by ultimately rooting itself in reality and humanity. By the time it reaches its enchanting climax, Ink ultimately reveals itself to be a very moving story about a strained father-daughter relationship that sadly can’t hold up to either’s expectations of reality. Ink is a very beautiful film that should be as renowned as the cult fantasy find of the century, Tarsem’s beautifully accomplished The Fall.


24. The Pledge (2001)

The Pledge (2001)

Sean Penn’s third feature directorial effort (after the gritty and underrated nineties efforts The Indian Runner and The Crossing Guard) stars Jack Nicholson as a recently retired detective who can’t get the unsolved murder of a young girl, or his promise to her mother to bring her killer to justice, out of his mind.

Nicholson gives an as-usual great performance, only this time one that lacks his world-famous charisma and is instead drenched in humility. Next to About Schmidt, this is one of the least flashy and most subtle roles of his career.

It’s truly refreshing to see one of the most charming movie stars of all time drop his million dollar persona and take on the role of an elderly everyman who just isn’t taken as seriously as he used to be. The Pledge succeeds both as the suspense thriller it is disguised to be and as the examination of aging and obsession with the past it actually is.


23. Jeff Who Lives At Home (2012)

Jeff Who Lives at Home

Jason Segal and Ed Helms star in this independent-minded but sincerely heartfelt comedy. Segal plays Jeff, a lost thirty-something stoner who lives in his mother’s (Susan Sarandon) basement.

Jeff is a wonderfully likable, if not emotionally stunted, character that literally spends his time waiting for a sign to give his life direction. When he gets that sign in the form of a wrong number, the film takes us on something of a miniature road trip as Segal’s whims and instincts take him all over town for a series of adventures and chance encounters, including reconnecting with his slightly estranged older brother (Helms).

Segal successfully carries the weight of the film in an endearing and sensitive performance that still needs a larger audience.


22. The Woodsman (2005)

Kevin Bacon in The Woodsman

Kevin Bacon gives one of the bravest performances of his career as a child molester recently released from prison and who is genuinely trying to live right in the real world to make up for his past.

It’s no surprise that the film didn’t easily find an audience, given the subject matter and the film’s refusal to demonize a character capable of such a heinous act. Truly adult films like The Woodsman, which refuse to rely on black and white depictions of humanity, have to fight to be seen and heard today.


21. The Singing Detective (2003)

The Singing Detective (2003)

Robert Downey, Jr drops his drool-worthy charisma and gives a raw, angry performance about a man simmering and rotting in his own personally constructed hell. Downey plays an unlikable and misogynistic hospital- ridden writer who confuses one of his creations (a 1950’s detective investigating the murder of a prostitute) with reality.

Directed by Downey’s Back To School costar Keith Gordon, The Singing Detective is a funny, disturbing, and moving ride, truly unforgettable to those who have seen it, but largely unknown to most everyone else.