MEME
If your life was a movie, what would the soundtrack be? So, here's how it works:
1. Open your music library.
2. Put it on shuffle.
3. Press Play.
4. For every question, type the song that's playing.
5. When you go to a new question, press the Next button.
6. Don't lie and try to pretend you're cool.
7. Don't skip songs.

I was tempted to cheat, but didn't, and I'm doing this at work since I don't have all my songs at home at the moment due to hard drive breakage, but here's what I came up with:

(1) Opening credits: 'Our Frank' - Morrissey
(2) Waking up: 'Exile' - Gary Numan
(3)First day at school: 'Jerk-Off' - Tool
(4) Fight song: 'No Dark Things' - Echo & The Bunnymen
(5) First Date: 'Make Love' - Daft Punk (Apparently I work fast.)
(6) Breaking up: 'Hollow Hills' - Bauhaus
(7) Happiness: 'Reel Ten' - The Plugz
(8) Life is okay: 'Pale Clouded White' - Cocteau Twins
(9) Mental breakdown: 'I'm Still In Love With You' - Al Green (So true.)
(10) Driving: 'Yellow Cake' - Ministry
(11) Flashback: 'Splish Splash' - Bobby Darin
(12) Getting back together: 'P.S. Goodbye' - The Chameleons
(13) Prom: 'It's Alright Ma (I'm Only Bleeding)' - Bob Dylan
(14) Graduation: 'Anthems For A Seventeen Year-Old Girl' - Broken Social Scene (Nice!)
(15) Wedding: 'Malpractice' - Faith No More
(16) Honeymoon: 'Laugh The World Away' - Mission of Burma
(17) Birth of a child: 'Outside The Trains Don't Run On Time' - Gang of Four
(18) Final battle: 'My Wave' - Soundgarden
(19) Death scene: 'Black Wave' - The Shins
(20) Funeral song: 'Drive My Car' - The Beatles
(21) End credits: 'Highway 61 Revisited' - Bob Dylan