This is based on opinion. Please don't list it on a work's trope example list.
Tear Jerker / Josh Groban
His version of "I'll Be Home For Christmas", an already normally tear-jerking song. The beginning and end are radio messages to soldiers overseas from their children. The worst:
Eight-ish year old girl: Hi, Daddy. Mommy, Bella, and I wrapped our presents today. We saved some special for you so you can open them when you get home. I hope you'll be able to come home soon. I love you.
His version of "Canto Alla Vita", for whatever reason.
"To Where You Are" and "Broken Vow" can send one into crying jags.
Then there is "Awake"
"You Are Loved (Don't Give Up)" can make some people struggling with depression burst into sobs. That'd make the song powerful enough on its own, but combine it with Josh Groban's voice...