I love remembering things by the song I was listing to at the time.
I remember being out cycling the first time I heard Green Day's - American Idiot.
I remember traveling on the bus going to college the first time I heard AC/DC's - Fly On The Wall and as you have said yourself there is nothing like game music to bring back memories. The soundtrack of Gran Turismo 1 and Crash Team Racing bring back the most game memories for me.
"In My Life" by The Beatles. To me the lyrics are so much deeper than "Yesterday". Also the song "Western Movies" by The Olympics this is the very first song that can remember hearing. I wore that 45 out on our portable record player.
"On the Wings of a Dove", "Little Brown Jug", and "Hole in the Bottom of the Sea" - My dad and I used to sing on the way to and from hunting or fishing trips... beats the hell out of the radio...