20. Take This Waltz (2011)
Writer-director Sarah Polley (the lead child star from Terry Gilliam’s The Adventures of Baron Munchausen) wrote and directed this wonderful film, which offers the (rare) female perspective on infidelity. Michele Williams stars as woman who really has nothing to complain about in her life or her marriage (to a very likable and real Seth Rogen), but soon begins wondering what could be when she falls for a passionate and free-spirited artist living across the street.
Take This Waltz doesn’t condemn or condone, it makes you understand Williams’ point of view just enough to see why she does what she does. Williams doesn’t shy away from the character’s weaknesses, and gives as strong and as daring of a performance as her excellent and noted work in Blue Valentine.
On many different levels, Take This Waltz is that rare, profound movie (much like Annie Hall) that is able to gently and astutely show us some of the brutal and heartbreaking truths behind romantic relationships.
19. Repo Men (2010)
If it actually was the eighties cult sci-fi classic it feels like, Repo Men would have been a big financial bomb upon its theatrical release only to be rediscovered on home video a few years down the road. Since it was made and released twenty years later, unfortunately, it has so far only managed to accomplish the former while still patiently waiting on the latter.
Jude Law and Forrest Whittaker star in this darkly comedic futuristic tale as men who work for an agency that leases artificial organs to dying clients. When said clients are unable to meet their monthly payments, it’s up to employees like Law and Whittaker to reposes their boss’ property… And forget the fact they’re taking a life in the process. When Law is injured on the job and needs one of the artificial organs to survive, he soon finds himself a victim of his own livelihood.
With a great mix of satire, action, and wit, Repo Men is the kind of movie that should be the norm in popular cinema today. Instead, the qualities that make it stand out are also what probably keep it hidden amongst the more obscure titles on this list.
18. Surveillance (2008)
Director Jennifer Lynch’s Rashomon-style thriller centers around a brutal, unsolved murder on the back roads of small-town America. The numerous witnesses to the crime all have wildly different stories to tell, and the FBI agents (spot on and wonderfully fun performances by Bill Pullman and Julia Ormond) sent to investigate are unable to tell if anyone knows more than they’re saying.
Surveillance is a completely and utterly twisted thriller that refuses to give its audience any form of comfort. It is the kind of film we wish all the stale thrillers we’ve watched in the last decade would have the courage to be: uncompromising, fresh, and surprising until the very end. Surveillance easily rises above the vast majority of such films and is a worthy companion to some of David Fincher’s best (and bleakest) works.
17. The Specials (2000)
The superheroes that are the focus in this film (known and grouped together as “The Specials:) are neither heroic nor selfless. They bicker amongst themselves over who is the most popular, sleep with each other behind their partners’ backs, and narcissistically obsess over how accurate their merchandising toy line depicts their likenesses. These heroes’ notoriety has turned them into spoiled and childish babies, and the results are hilarious and pure fun to watch.
Before he made his name as a director with the cult hits Sliver and Super (not to mention last year’s international smash hit Guardians of the Galaxy), James Gunn wrote and starred in this little known comedy. His quirk and brilliance shined early on for the few people who saw and appreciated it. Probably too ahead of its time for its own good, The Specials is well worth the effort to check out for those dying for the rising writer/director’s next effort.
16 and 15. Snow Angels (2007) and Prince Avalanche (2013)
David Gordon Green is one of the most interesting American directorial finds of the twenty first century. His Malick-inspired indies that focus on rural, small town atmosphere and characters (from George Washington to All The Real Girls to Joe) all rightfully garnered him the respect and attention of critics and serious film goers.
The mass public also knows him, but more so for such hugely entertaining, larger budget stoner comedies like Pineapple Express and Your Highness than for the quieter work that gave him a career. Eclectic doesn’t even begin to describe Green’s body of work. You almost have to view him as two different men with two different careers, because there’s absolutely no through line between the two worlds other than his name being in the credits.
Snow Angels and Prince Avalanche fall into the category of Green’s rural-set and character-driven works. Snow Angels is the darker and more violent of the two, while Avalanche is a bit more relaxed and comical in tone. Both films have a flair for the eccentric, unfold at a peaceful pace, and display a subtle but melancholic tone. As unique as his career is, Green’s finest films are even more so. As is often the case with many filmmakers, however, his best quality work isn’t always his most widely known.
14. Sex & Death 101 (2007)
Heathers screenwriter Daniel Waters wrote and directed this sometimes-surreal dark sex comedy about a man who receives a mysterious email containing a list of all the women he’s ever had and will ever have sex with.
Stars Simon Baker and Winona Ryder (highly welcomed back into Waters’ world) successfully and effortlessly wade through the always-fluctuating tone of the script. Waters’ highly individualistic style of writing and storytelling is on full display in the film, and the result is the writer’s best-produced (and very unnoticed) work in decades.
13. Numb (2007)
Former Friends sitcom star Matthew Perry delivers a moving and funny performance as a neurotic Hollywood screenwriter struggling through a unique and challenging mental disorder known as Depersonalization Disorder. He subsequently goes through a hilarious and terrifying series of trials and errors with different psychiatrists and medications, only to discover no one entirely knows what they’re doing and that every possible solution is nothing more than a (often not so) educated guess.
Both a wonderful character study and a very telling satire of the psychiatric field, it’s hard to say why Numb or Perry’s performance have yet to receive any real recognition. Perhaps Perry’s still-enormous popularity as a sitcom star at the time of the film’s release hurt his chances at getting recognized for more mature work. Whatever the case may be, Numb is a strongly written (by Harris Goldberg, who also directed) and finely made work that is well worth your time.
12 and 11. Chuck & Buck (2000) and The Good Girl (2002)
For a brief period of time at the beginning of this century, it looked like writer Mike White and director Miguel Arteta were going to be two of the major voices in popular American independent film. While both their careers have held on strong, they haven’t quite been able to continue on the same path started by their early mineshaft-dark comedy collaborations.
Chuck & Buck stars White as an overgrown man-child who has just lost his mother. Clinging to the past, White sets off for Los Angels to seek out the company of his childhood friend (Chris Weitz). Weitz is now an adult with a wife and a high-class job as a music industry executive.
What ensues is a very uncomfortable, disturbing, and ultimately moving series of awkward encounters between the two (former) friends. Equally disturbing as it is hilarious, Chuck & Buck is a sometimes-painfully uncomfortable experience that somehow manages to be just optimistic enough so it doesn’t wallow in its own darkness.
The Good Girl stars Friends star Jennifer Aniston as a married small town woman who starts an affair with a younger, disturbed grocery store coworker (a great early weirdo performance by Jake Gyllenhaal). Aniston is fantastic as the unhappy woman who is forced to ride the waves of her poor decisions.
Both films are two of the best (and sickest) under-known dark comedies of their time.