Big Star's "Way Out West" (Radio City, Ardent):
Alex Chilton has an incredible ability to convey total wistfulness and longing. Not to mention the fact that he just sounds so damned bittersweet.

Bauhaus' "Crowds" (In The Flat Field, 4AD):
I guess when I'm upset, I really want to hear songs that are actually just bilious vitriol masquerading as ballads. This one's particularly good, because Peter Murphy has us actually believing he's in pain, only to crack an evil grin and spit on us. Yeah.

Dead Kennedys' "Moon Over Marin" (Plastic Surgery Disasters, Alternative Tentacles):
Perhaps a bit of a stretch, but this song still belongs on the list. A bleak view of the world, and yet, it's so weirdly hopeful in its own way...

Dead Moon's "It's OK" (Crack In The System, Tombstone):
This is a supportive song. It's what you'd want your friends/parents/whoever to sing to you when you were down, if your friends/parents/whoever were half as rocking as Dead Moon!

Rites of Spring's "Persistent Vision" (Rites of Spring, Dischord):
You couldn't very well have a soundtrack to melancholy without including the founding fathers of emo. They still do it better than everybody else, and they're not even doing it anymore.

Modern Lovers' "Hospital" (Modern Lovers, Rhino):
Nothing else feeds the self-indulgent maudlin like this one.

The Damned's "I Just Can't Be Happy Today" (Machine Gun Etiquette, Cheswick):
Just like last week, this one speaks for itself.

White Stripes' "Jolene" (Jolene/Hello Operator picture disk, Sympathy For the Record Industry):
A Dolly Parton classic -- a wife begs a femme fatale to pass over her man. "You could have your choice of men, and I could never love again..." I get weepy just thinking about it.

Glenn Danzig's "Less Than Zero" (Less Than Zero Soundtrack, Def Jam):
Perfect for when you're feeling lonely, less than zero. Elvis' "Heartbreak Hotel" for the cocaine generation.

Mission of Burma's "That's When I Reach For My Revolver" (Signals, Calls and Marches, Ace of Hearts):
Songs about guns aren't always angry songs.

Knoxville Girls' "He Stopped Loving Her Today" (Knoxville Girls, In The Red):
What is it about punk/indie rockers covering country classics that makes such good chum for the sharks of angst in the sea of despair?

Roxy Music's "Mother of Pearl" (Stranded, Atco):
I know I get depressed when I'm stranded at a disco. All joking aside, this is a very sad song.

Hanson Brothers' "You Are Not For Me" (Gross Misconduct, Alternative Tentacles):
My god, what could be worse than being told that?!

The Gories' "6 Cold Feet" (I Know You Fine, But How You Doin', New Rose):
Songs about death and lonely graves automatically qualify.

The Pogues' "Waltzing Matilda" (Rum Sodomy and The Lash, MCA):
You think you've got it bad? The guy in this song has no legs. And now Shane MacGowan has no teeth.