5. American Beauty
Sam Mendes' "American Beauty" was one of the most celebrated and acclaimed dramas of 1999, winning Academy Awards for Best Picture, Actor, Director, Screenplay, and Cinematography, as well as being nominated for several others. The story is that of middle-aged writer and ad-exec Lester Burnham who develops an infatuation over his teenage daughter's best friend Angela, played by Mena Suvari. Kevin Spacey was brilliant in the lead role despite the studio being against his casting. There's a pretty heavy amount of WTF in this movie, with different themes being explored and multiple interpretations, but ultimately it's about a guy with a pretty severe midlife crisis. The ending of the movie sees Lester being murdered by his neighbor, just moments after it looked like his desires for Angela were finally going to be fulfilled. The film doesn't really have a sympathetic character and nothing good happens to anybody involved, which is exactly why it was so well-received. Can you imagine if Lester and his wife had resolved their issues and lived happily ever after? No, thanks.