5. The Room (Tommy Wiseau, 2003)
There are certainly people who find a few of the entries on this list of questionable cinematic quality, but The Room has the distinction of earning its place precisely for being undeniably bad. Tommy Wiseau’s mysterious origins and wealth are the stuff of legend (and a recent biopic with James Franco), but the film stands well on its own without the whole cult around it.
And by “stands well on its own”, I mean it is gloriously awful. The dialogue is repetitive and the plot is nonsensical at best, the uncomfortably long sex scenes are scored and shot as tackily as the human mind can possibly imagine, and Wiseau’s acting is cringe-worthy in such a level that it also makes his performance (and his movie) infinitely watchable and hilarious.
4. Mean Girls (Mark Waters, 2004)
It’s hard to think of a more influential teen comedy this century. While also a mainstream success, Mean Girls earns its place a cult favorite because it inspired a true myriad of oft-repeated quotes and special dates (“It’s October 3rd”) among its fans, and cemented its characters in pop culture in a way that no film of its genre did in the last two decades.
The fact is Mean Girls stands as one of the smartest teen comedies of all time, as much a biting and absurdist satire on multiple dimensions as a true-to-life account of high school gender politics and its consequences on people’s behavior and psyches. In short, if you think Mean Girls doesn’t deserve its place on this list, who cares – you don’t even go here!
3. Eternal Sunshine of the Spotless Mind (Michel Gondry, 2004)
While sitting atop many “best scripts of the 21st century” lists around the internet, Eternal Sunshine never quite became a quirky mainstream hit like previous Charlie Kaufman films Being John Malkovich and Adaptation. It has, however, attracted a considerable cult following with its doomed love story inspiring and puzzling a lot of cinephiles around the world.
As Jim Carrey and Kate Winslet dance around each other in some of the best work of both their careers, Kaufman’s careful surrealism goes off the rails for many stunningly beautiful scenes directed with a deft hand by Michel Gondry. Clocking at under 2 hours, this romantic sci-fi drama is just weird (and good) enough to merit cult status.
2. Oldboy (Chan-wook Park, 2003)
Praised in filmmaking circles as a true classic of the 21st century, Chan-wook Park’s revolutionary revenge tale has proven itself an enduring cult classic in the 15 years since its initial release. As a new generation of cinema lovers discovers it, its status should only grow and its importance should only become more evident than it already is.
Park has gone on to make many other films, some equally stunning (The Handmaiden, Lady Vengeance), some not so much (Thirst, Stoker), but he’s never less than surprising and entertaining, qualities that are on full display on this violent, dark, twisty thriller that rightfully launched him into international recognition.
1. Donnie Darko (Richard Kelly, 2001)
You knew Donnie Darko would be at the top of this list, and that’s because, regardless of what you feel about Richard Kelly’s divisive and mysterious debut feature, you and I both know that its cult following is unmatched in 21st century cinema. The moody story of a troubled teenager plagued by visions of a large rabbit influencing him to commit crimes is obsessively analyzed and re-watched by a group of die-hard fans all around the world.
Truth is, the film has a lot of great qualities. Jake Gyllenhaal’s performance is a prescient demonstration of his prowess as a purely physical actor, while Kelly helms the film with confidence and self-indulgence that only a first-time director could muster. It might be a controversial movie, but it’s an undeniable inclusion on this list.