Wow, this is one cool game, I must try it. Ok, here goes.
Opening: Someone Put Your Hand Out by Michael Jackson
Birth: Vanilla Twilight by Owl City (um, ok...)
First Day of School: Love You Madly by CAKE (While it is kind of a love song, I can definitely imagine walking into school with this music blaring)
Falling in love: The Largo LaGrande Theme - Monkey Island 2 Soundtrack (Well, I do like the upbeat Jazz feel to it, so I guess it fits

)
Fight scene: Got to Move by CAKE (If it was in slow-motion, sure

)
Breaking up: Sergeamt Pepper's Lonely Heart's Club Band by The Beatles (I guess I was pretty happy to be rid of her

)
Prom: Teenage Pregnancy by CAKE (God, I lol'd when I heard that, cause goodness knows what goes on at those things

)
Life: Crescendolls by Daft Punk (yeah, I s'pose that works)
Mental Breakdown: You Are Not Alone by Michael Jackson (PERFECT!)
Driving: Phatt Island - Monkey Island 2 Soundtrack (It is kinda bluesy, and I like that, so for me it fits)
Flashback: Commissioning a Symphony in C by CAKE (that works pretty well, not great for a flashback, but it works)
Wedding: Something About Us by Daft Punk (It's...weird)
Birth of child: Lucy in the Sky With Diamonds by The Beatles (I think that works really well)
Final Battle: Fall Again by Michael Jackson (YES! It has an epicness about it, like I'm slowly building myself up for a big battle)
Death scene: Lady In Red - Altiyan Childs cover (It's sad sounding enough I guess, but I'm not a lady

I could be singing to a loved one as I die or something though

)
Funeral: Wanna Be Starting Something (Ok, WTF is this, maybe my friends are out for blood for my murder? Idk, the title suggests that whoever killed me started a war)
End credits: A Dimension of Pain - Monkey Island 2 Soundtrack (Now that's just silly)