My redneck is showing, but Dixie Chicks, "Wide Open Spaces" because it came out as I went to college in Arizona (wide open spaces in the west) and the description of the parents in that song pretty much encapsulated my parents reactions to me going to college.

The "Saras" have gotten me through basically every breakup ever. (Sara Evans, Sara Bareilles, Sarah McLachlan).

I have strong associations with stupid dance songs. I learned the macarena from the older "cooler" kids on a church trip and I always think about it and that trip. "Hey Mickey" reminds me of my friend Tiffany who knew all the moves to the dance to that song and would lead us all in it during middle school dances. Learned "Mambo Number 5" on an exchange trip to Germany in high school (six months before it became big in the US my hipster wanted me to tell you) and there was a bar dance to that song too but it never made it over to the US.