It's funny how our minds connect a song to a specific location or time in our life. The instant you hear a song you've all but forgotten about, it's as if you enter a time machine and are immediately transported back in time.
In that sense, consider the name of your time machine to be Retroj.am.
Upon visiting the site, you're asked to enter your birthdate. Within seconds the service returns a Spotify playlist for each of your educational years, but not before starting with the year you were born.
You can then choose to listen to the playlist in Spotify (with a free account), or purchase the entire list in iTunes.
It's too hard to pick just one favorite playlist, for me at least. Each playlist brings back another time in my young adolescence I appreciate for different reasons. I'm sure you'll find the same thing as you scroll through the years, laughing and gasping.