I found this fun idea on the blog of 
Day 01- A song from your childhood.
Day 02 - A song that reminds you of your most recent ex.
Day 03 - A song that reminds you of one/both of your parents.
Day 04 - A song that calms you down.
Day 05 - A song that is often stuck in your head.
Day 06 - A song that reminds you of a best friend.
Day 07 - A song that reminds you of the past summer.
Day 08 - A song that reminds you of your first love.
Day 09 - A song that makes you hopeful.
Day 10 - A song by your favorite band.
Day 11 - A song on the soundtrack of your favorite movie.
Day 12 - The last song you heard.
Day 13 - A song that reminds you of a former friend.
Day 14 - A song that reminds you of your boyfriend/girlfriend.
Day 15 - A song you love singing along to.
Day 16 - A song that has made you cry.
Day 17 - A song that makes you want to dance.
Day 18 - A song you love but rarely listen to.
Day 19 - The first song alphabetically on your iPod/iTunes.
Day 20 - The last song alphabetically on your iPod/iTunes.
Day 21 - Your favorite song.
Day 22 - A song that someone has sung to you.
Day 23 - A song that you cannot stand to listen to.
Day 24 - A song that you have danced to with your best friend.
Day 25 - A song that you could listen to all day without getting tired of.
Day 01- A song from your childhood: Grandmaster Flash, Melle Mel and the Furious Five, The Message. I remember hearing this for the first time from a friend's older brother's boombox, and being mesmerized. I stopped shooting baskets in our game of 'horse' and just sat down and listened.
Day 2: A song that reminds you of your most recent ex. My last ex was over a dozen years ago, but because she ran a Sleepytime Gorilla Museum fan site, I can't help but associate her with that band. Here is a highlight from their first (and best) album: Sleep is Wrong from the LP, Grand Opening and Closing.
Day 03 - A song that reminds you of one/both of your parents. This would have to be Jackie Blue by The Ozark Mountain Daredevils.