Picking the creepiest love story in Happiness (yet another dark Todd Solondz classic) is almost like being asked to pick James Spader's creepiest role. They're all very, very different, but equally worthy in their own way. In this case, however, in a story about a family in which a happily married pedophile roams free, his sister-in-law fantasizes about being sexually assaulted, and the other is dating Jon Lovitz (or, was—he commits suicide), we're going to run with Philip Seymour Hoffman, who overcomes a lot of competition to be dubbed the movie's most overtly creepy character.
As Allen, the town's resident obscene phone-caller, he gets his kicks on dialing up the film's leading ladies and describing in detail the things he'd like to do to them while engaging in a bit of self-servicing. Little does he know that his call to his sexy neighbor-crush Joy (Lara Flynn Boyle), the aforementioned sister, will result in a challenge to follow through on those bold claims. From there, we witness one of the most awkward relationships in the history of film take flight.