Well, I'll give this a go. I don't know how well it'll work for me, since I'm just opening up my CD folder and randomly picking CD's and songs, but lets see how it ends up.

-Opening Credits: Tirlee, Tirlo -- UW Women's Choir
Apparently, my movie starts somewhere around Christmas at one of the multi-choir concerts I took part in. And no, I wasn't in this particular group!

-Waking Up: Ballad of Barbara -- Johnny Cash
A great song actually. The beginning is good for waking up I guess. But I doubt I'll ever end up with anyone named Barbara.

-First Day At School: Eine Kleine "Not" Music -- Gashouse Gang
A barber quartet parody version of Mozart's Eine Kleine Nacht Musik. It mentions Mozart's Magic Flute opera throughout... it would be a pretty fucked up first day of school.

-Falling In Love: Piano Black -- Yoko Kanno and the Seatbelts
Good song from the anime Cowboy Bebop.

-Fight Song: Why don't you love me (like you used to do?) -- Hank Williams Sr.
What kind of fucked up movie is this? Am I beating up the person I'm in love with, or vice versa?

-Breaking Up: Certainly Lord -- UW-Concert Choir
This song starts out asking "Have you got good religion?" Apparently, I don't have good enough religion to stay together with whomever I'm with.

-Prom: Salty Chocolate Balls -- Chef
Damn, that's one hell of a Prom!

-Life: Je suis venu te dire que je m'en vais (I came to tell you that I'm going away)- Serge Gainsbourg
Where am I going away to? That's a really sad life.

-Mental Breakdown: Ces gens-là (Those people) -- Jacques Brel
On short French kick it looks like. Coincidentally, this song fits fairly well here, even though, Brel play a whining character in this song.

-Driving: Amazing Grace -- UW-Chorale
Finally! A choir from my university I took part in! I must have really divine driving I guess.

-Flashback: Dirty Song -- (I don't know who it's by.)
...0_o

-Getting Back Together: Road to the West -- Yoko Kanno and the Seatbelts
This one fits well. Good to have some more Cowboy Bebop on here.

-Wedding: Tearin' it up (and Burnin' it down) -- Garth Brooks
Now that sounds like a fun wedding! We do get pretty trashed at Wisconsin weddings.

-Birth of Child: Viens Malika (Come Malika)-- Lakme
A really beautiful Opera duet. Very fitting for the birth of a child, if I were naming it Malika.

-Final Battle: The Chance -- Lockwood
Well, at least it's not a forgone conclusion that I lose.

-Death Scene: Blame Canada -- Robin Williams
Yeah, it's all their fault! They did this to me! They're not even a real country anyways!

-Funeral Song: Ma plus belle histoire d'amour (My most beautiful love story)-- Barbara
Well, a lot of people who love me will visit my funeral then at least. By the way, a really beautiful song.

-End Credits: The Wall -- Johnny Cash
"Nobody ever climbed that wall, but I'm gonna be the first..." Fitting end.

This was a fun exercise Twitch. I wish I could find more things like this.