Dia Frampton's Don't Kick the Chair. I cried mself to sleep listening to it a few months ago and I'm about ready for another session, college is too much sometimes
Hillsong United - All I Need Is You
Hoobastank - The Reason
Enrique Iglesias feat. Nicole Scherzinger - Heartbeat (memories )
Adele - Make You Feel My Love
Shakira - No -> This song makes me so sentimental any day at any minute, I cry almost everytime.
Kelly Clarkson - Sober
Jennifer Love Hewitt - Take My Heart Back -> The first part of this song slays me so hard I cry almost everytime.
Nelly Furtado - In God's Hands ->
Britney Spears - Everytime
I heard Wish You Were Here for the first time soon after the unexpected death of someone close to me, and I bawled. I can listen to it now and it doesn't sadden me, but it always reminds me of how I was feeling at that point in time