"Angel" by Sarah McLachlan--> End of summer. I first heard it when the Lilith Fair came to Toronto in August, 1997, about two weeks before school started.
"Home for a Rest" by Spirit of the West--> Basically my entire four years of undergrad. They played it at quite a bit when I was a frosh and also at class of 2002 formals that were held each year. I think it had to do with the song appearing on the "Frosh" CD the year I started university
"Stop" by the Spice Girls-- hitting the clubs with my floormates in first year
"Foolish Games" by Jewel-- Valentine's Semiformal '98. I got to dance with my non-date crush item
"All I Want To Do Is Be With You" by Mr. Big(g?)-- Sitting in a bar in Paris, France 2001 with several people from my study abroad program and we sang along with the CD. One guy had never heard the song before (I first heard it in spring 1992)!