Wow, that's a great topic indeed. I don't think Mark's catalog is a good source for cry-inducing songs specifically, but everything already listed can give you some chances to shed tears depending on the situation. Usually, and I mean always, his songs bring optimism and happiness and I cry because of happiness if you know what I mean. The feeling Bob Dylan described in one of his songs as “It frightens me, the awful truth of how sweet life can be.”
On Every Street makes me emotional when I merely recite lyrics in my head: "There's gotta be a record of you someplace", "And you still refuse to be traced", "Somewhere your fingerprints remain concrete", etc.
The Alchemy introduction to Tunnel Of Love live version and the song itself gave me probably the biggest emotional dives in my life when I was a kid, I just went straight to the cosmos listening to it on repeat. It's probably the ultimate tears shedding song MK ever got.
