So, here's how it works:
1. Open your library (iTunes, Winamp, Media Player, iPod, etc)
2. Put it on shuffle, for every question, type the song that's playing
3. Press play
4. When you go to a new question, press the next button
5. Don't lie and try to pretend you're cool...
Opening Credits: Super Mario Bros. 2 Theme (Gypsy Jazz) / Adrian Holovaty
Waking Up: No Woman, No Cry / Bob Marley & The Wailers
First Day At School: Asleep on a Sunbeam / Belle & Sebastian
Falling In Love: Golden Brown / The Stranglers
Fight Song: White & Nerdy / "Weird Al" Yankovic
Breaking Up: Alabama Song / The Doors
Prom: Two Out of Three Ain't Bad / Meat Loaf
Life Is Good: Both Sides Now / Dolly Parton (please don't laugh)
Mental Breakdown: Landslide / Smashing Pumpkins
Driving: Suddenly I See / KT Tunstall
Flashback: Overture / Katamari Damacy
Getting Back Together: Something / The Beatles
Wedding: I'll Never Tell / Xander & Anya
Birth of Child: Back to the Future Overture / The Outatime Orchestra
Final Battle: Africa / Toto
Death Scene: When I Fall / Barenaked Ladies
Funeral Song: They Got Lost / They Might Be Giants
End Credits: Come Back From San Francisco / The Magnetic Fields