You asked for it....
You Were Meant for Me, Foolish Games -Jewel
Faithfully, Open Arms -Journey
He's Not Heavy, He's My Brother -nothing like them playing this at your uncle's funeral and seeing his four grown brothers (including your dad) crying like babies.
The Dance -Garth Brooks... oh hell, a lot of his stuff does it to me (Much Too Young)
Every Rose Has It's Thorn -Poison
Sad Songs and Waltzes by Cake
Imagine -John Lennon
Dust in the Wind -oh come on, for who does this not apply?
What it Takes by Aerosmith
Girl From Yesterday, Learn to be Still, Wasted Time -The Eagles
Babe, Show me the Way -Styx
To a lesser extent -Knockin on Heaven's Door by Dylan, Dream On by Aerosmith
There's a couple dozen more that might do the trick depending on the circumstances, like Tuesday's Gone, Freebird, Objects in the Rearview Mirror, Don't Speak (No Doubt), Rebels (Tom Petty), Thunder Road (Springsteen), Space Oddity (Bowie), Time after Time (Cyndi Lauper, yeah, mock me), American Pie....
Whew, and that's just off the top of my head, I wonder what I'm forgetting. And don't even get me started on Pink Floyd songs
I've considered making a "Music to kill myself to" CD several times, I really should. You think this is a long list, I have a friend that I swear lives to listen to music that depresses him