The Virgin Suicides (1999)--Five beautiful blonde chicks off themselves. It doesn't get any lower than that. Sofia Coppola's directorial debut--based on a popular book--is about a pride of depressed sisters, led by Kirsten Dunst, who can't stand conventional '70s suburbia. James Woods and Kathleen Turner are great as the repressive 'rents, and Josh Hartnett is the epitome of a dreamy high school stud.
Seven (1995)--One of the best films of the '90s, and a real bummer, David Fincher's bleak serial killer thriller is moody, dark, despairing, and, like Barton Fink, one of the great "head in a box" films. But don't let that stop you from enjoying it. The DVD is a two-disc set, with lots of extras and audio commentaries that trick you into watching the bleak, inexorable ending march toward you again and again.
Timecode (2000)--The last 90 minutes in the life of a bummed out movie producer. Mike Figgis' experimental film, in which four DV cameras capture simultaneous actions in different but connected locations, is a grand failure only because the parody of the movie industry is too Altmanesque. With all the extras on this disc you can breathe the despair for 810 minutes. Stellan Skarsg#229rd leads a great cast as the doomed mogul.
Loser (2000)--'Cause that's what you are. This off-kilter knockoff of Billy Wilder's masterpiece The Apartment, starring Mena Suvari and written and directed by Amy Heckerling (Clueless), isn't as funny as its mentor, but that's the point. What better way to ring in the new millennium than with an unfunny, predictable teen comedy that reminds you of how your school years were even more of a failure because yours didn't have a happy ending.