I was browsing DA and stumbled into OhmGueil's profile, where he had this weird journal entry ([link]).
In a nutshell: Load your whole playlist, set it to random and note down the songs that turn up for each event.
I actually did it twice, because my first playlist wasn't quite right, and it also is a whole lot of fun. Anyway, I'll stick to the first one.

My Life's Soundtrack:

*Opening Credits: Glory or Pain short (Knights of Honor)*
The soundtrack of a medieval strategy game. I copied that once because I thought it might make good RPG music, but it really makes a great opening credit, with drums and brass.

*Waking Up: No Milk Today (Herman's Hermits)*
Don't like milk anyway Not something I'd like to get up to, but so's life.

*First Day at School: Solid Iron Heart (Chris Whitley)*
"Meet me on the other side" So, let's do this...

*Falling in Love: All My Money Back (Blues Brothers)*
Something tells me this love isn't gonna last.

*Fight Song: Shot Gun Blues (Blues Brothers)*
That's some seriously depressive blues. "The blues is falling/Falling down on me like rain/I'm gonna take a shotgun now people/And disconnect my brain." OK, let's not be hasty...

*Breaking Up: Der Untote (Schandmaul)*
Medieval-Rock, and also quite fitting, about an undead who hurt everyone when alive and now wanders the world powerless and alone. Ye been warned.

*Prom: Money for Nothing (Dire Straits)*
You get rewarded for doing nothing much - is that what school taught us? Not really fitting, but that's random for you.

*Life: Foo Foo (Santana)*
That's a good one. No one really knows what this song is about, but it's happy and loud. That's life!

*Mental Breakdown: Sherwood Forest Rap (Men in Tights Soundtrack)*
Great song for a breakdown.

*Driving Far Away: Ohrwurm (Wise Guys)*
Song about songs you can't get out of your head. Maybe I'm trying to escape them.

*Flashback: Wonderwall (Paul Anka)*
"You're gonna be the one who saves me" - great, my flashback helps me!

*Wedding: Shortwave Radio (John Mayall & The Bluesbreakers)*
Why do all my love events wind up having blues in the background?

*Birth of Child: Couldn't Have Said Iit Better (Meat Loaf)*
Great. "You got that smile and you say nothing at all/ Well I couldn't have said it better myself".

*Final Battle: Just You Wait (My Fair Lady)*
A final battle with this soundtrack would look quite ridiculous, but on the other hand, it's about getting back at the person who tortured you for a long time, so...

*Death Scene: The Storm (Blackmore's Night)*
Not bad, starts slow, fast middle, slow ending with guitar only.

*Funeral Song: You're My Best Friend (Queen)*
"Oooo, you make me live"... Pff, joker. But at least I'll go appreciated.

*End Credit:Sie Will Mich (Prinzen)*
Strange one, about the fact that if you get what you want, it turns out to be something different. So maybe an appropriate end credit.

Try it, it's fun. Strange, but fun.