Easiest way for me to cry is to listen to Tumble in the Wind. It's probably one of my favorite songs, but you can honestly hear the toll life took on him in his voice especially when you compare it to the way he sounded when he was younger. https://youtu.be/A_4N05coN2g
Also, I've really gotten into Yellow Walls lately. Never really liked it the first time I heard it several years ago, but heard it again a few months back and it stuck with me for some reason. https://www.youtube.com/watch?v=99LAONJ1c_0