10. The Room (2003)
The Room is a movie you truly have to see to believe. Everything about it is just... off. The story is nonsensical, the segues are jarring, the characters are borderline mentally disabled, and the dialogue is absolutely ridiculous. Directed, produced by, and starring Tommy Wiseau; the film follows the melodramatic love triangle between a banker (played by Wiseau), his fiancée (played Juliette Danielle), and his conflicted best friend (played by Greg Sestero). In recent interviews Wiseau has claimed that he knew all along how funny this movie was going to be, though nobody is buying it. This guy, directed and played his role as serious as Christian Bale on the set of Terminator Salvation. As you watch the movie you'll find yourself rolling on the floor laughing quite constantly. There are a few scenes in particular you should watch out for. Number one, the obligatory sex scene that is somehow more awkward than the kissing scene in Howard the Duck. Number two, when our main character claims that his girlfriend is "tearing him apart". Finally, number three, when our main character buys his girlfriend some flowers (it sounds mundane, but it's comedic gold). They don't call it "the Citizen Kane of bad movies" for nothing.
