6. Living in Oblivion (1995)
Making a film with almost no budget and in difficult circumstances can push any director and crew to the edge, and in Living in Oblivion, everything that could possibly go wrong on a film set does. Nick Reve (Steve Buscemi) is an idealistic director hoping to make a thoughtful indie drama. But his crew is apathetic, his actors are unfocused, and there’s no budget for anything, not even craft services. As his shoot spirals out of control, Reve’s patience and understanding begins to wear thin until he eventually snaps in glorious fashion.
Living in Oblivion is an indie film about the difficulty of making an indie film with an insider’s knowing about the creative frustrations of making a no-budget film. In fact, it was inspired by director Tom DiCillo’s experiences on his first film, Johnny Suede. It’s a very funny dark look at the frustrations of filmmaking and one any cinephile or aspiring director will enjoy.
7. The House Of Yes (1997)
Thanksgiving at the Pascal house is an unusual experience, but then again the Pascals are an unusual family: When son Marty visits home to introduce his fiancee Lesly, her presence has a serious affect on twin sister Jacqueline (Parker Posey), who has recently been released from a psychiatric hospital and has an obsession with Jacqueline Kennedy. When they end up stranded in the house due to a storm, things go from bad to worse when the disturbing nature of Marty and Jacqueline’s relationship is revealed.
This gleefully black comedy teeters on the brink of disturbing before falling right over the edge and then continues to plummet from there. With an incredible, manic performance by Posey and the debut feature film of the director of Mean Girls, The House of Yes–adapted from a play–is a dark comedy that depicts one of the most dysfunctional families ever committed to film.
8. Happiness (1998)
Director Todd Solondz again appears on this list, with Happiness being perhaps the darkest movie made in the past 20 years. Happiness features a number of hopeless and depressed characters, including a 30-something ESL teacher with pathetic dreams of being a musician and an emotionally stunted man who calls women on the phone to sexually harass them, but the most memorable character is a child molester who’s shockingly depicted with sympathy.
This unbelievably brutal film takes already difficult material and finds twisted humor in the increasingly awful situations in which its characters find themselves. Solondz’s nihilistic depiction of his characters and their lives inspires laughter from the audience, if only because it’s the only defense they have against the bleak situations he depicts on-screen.
9. Jerry and Tom (1998)
Jerry and Tom are both work associates and friends. They’re also contract killers, with Tom taking Jerry under his wing and showing him the ropes of their wicked business. As they move from one relatively disastrous contract to another, with Jerry messing up time and again, forcing Tom to step in and finish the job, the movie becomes both a comedy of errors and a look at the cold–blooded life of professional assassins.
As methodical a movie as its characters, Jerry and Tom finds dark humor in ostensibly amoral protagonists. This is a comedy without a moral or a happy ending, instead relying on the audience’s ability to look on dispassionately as two murderers-for-hire casually stroll through their job as blase as a bored retail clerk would. With a distinctly 90’s attitude reminiscent of Quentin Tarantino, Jerry and Tom takes a casual look at murder and those that perpetrate this crime.
10. Guest House Paradiso (1999)
Rik Mayall and Adrian Edmonson may not be familiar names to American audiences, but in the United Kingdom they’re best known as the hapless and low-living duo from the TV series Bottom. Guest House Paradiso, a (somewhat) movie adaptation of the series, features the actors playing very similar characters to their TV counterparts, two squalid, shabby bachelors who run the worst guest house in the UK in an isolated village neighboring a frequently disruptive nuclear power plant. Hoping to improve their shabby lives, when a group of well-heeled tourists end up staying at their accomodations.
Of course, this is all just an excuse for Mayall and Edmonson to enact their trademark brand of often gross and bleak humor, which culminates in a mass projectile vomiting scene that surprisingly resolves the film. While spotty, it can serve for some audiences as an introduction to the late Mayall’s better work, as he’s best known as Drop Dead Fred in the US but has had a long, productive, and often hilarious career on TV in the UK.
Author Bio: Mike Gray is a writer and academic whose work has appeared on numerous websites and maintains a TV and movie blog at mikegraymikegray.wordpress.com.