Tim McGraw/Tear Jerker

There's Tim McGraw's signature song, "Don't Take the Girl", in which the titular line takes on a different meaning every verse.
As well as "My Little Girl". It may cause certain fathers to cry Manly Tears.
And "If You're Reading This". a letter sent home from a dead soldier. Especially the line "There's gonna come a day... when you'll move on and find someone else... and that's okay."
"Grown Men Don't Cry" can, ironically, get certain people choked up.
"Live Like You Were Dying" The whole song is about how, when McGraw's father was given a terminal diagnosis, instead of sitting there, he went out and did all the things he was afraid to do, and encourages McGraw to do the same. His father dies during the song.

"And all of a sudden, goin' fishin'
Wasn't such an imposition
And I went three times that year I lost my dad."

The end of "Just to See You Smile," as posted under I Want My Beloved to Be Happy.
Also: "I've Got Friends That Do" and "When She Wakes Up And Sees Me Gone".
"Some Things Never Change" is an absolutely broken sounding song about unrequited love. "For A Little While" is an upbeat song about a summer romance -- and in its own way, just as heartbreaking.
"Please Remember Me". The possible interpretations for the lyrics get progressively sadder as you think of them.
"One of These Days", especially to those wrangling with self-hatred.