Don't take the girl by Tim McGraw i always cry and my woman my wife by Marty Robbins (oldies) both made me cry but my woman my wife if listen to it very sweet and sad song but it's an oldie so you guy would not know that song.
what hurts the most - rascal flatts
love dont run - steve holy (i think thats the name of the song)
letters from home - dont know who sings it !
pretty much all sad love songs and just plain sad songs can make me cry when i listen to them in a certain mood .
Whiskey Lullaby- Brad Paisley & Allison Krauss
Concrete Angel- Martina McBride
What Hurts The Most- Rascal Flatts
Thank You- Johnny Reid
Man I Want To Be- Chris Young
The list could go on forever. -_-
Concrete Angel by Martina McBride
Whiskey Lulaby by Alison Crauss (i think thats how you spell it.) and Brad Paisley
Fancy by Reba McEntire
Alyssa Lies by Jason Michael Carroll
Don't take the Girl by Tim Mcgraw
If Your Reading This by Tim Mcgraw
Moments by Montgomery Gentry
and im sure many others but those for sure