Considering his reputation for upbeat, tongue-in-cheek lyrics -- [[Music/BradPaisley This country singer]] [[TearJerker does quite a lot of these songs that can make you cry]].

* "When I Get Where I'm Going", particularly the chorus with Music/DollyParton.
-->"When I get where I'm going\\
there'll be only happy tears.\\
I will shed the sins and struggles\\
I have carried all these years.\\
And I'll leave my heart wide open\\
I will love and have no fear.\\
Yeah when I get where I'm going\\
Don't cry for me down here."
* "[[ Whiskey Lullaby]]" (with Alison Krauss) is a song about a man who finds his wife cheating on him. He's broken by it, and becomes a drunk, eventually committing suicide. When she sees what she did to him, she follows the path. If the lyrics themselves don't have you in tears, the video will, as it shows the man was coming home from a war and she was the only thing that had been keeping him going.
-->"He put that bottle to his head and pulled the trigger\\
And finally drank away her memory.\\
Life is short, but this time it was bigger\\
Than the strength he had to get up off his knees."
** Arguably worse are the two lines directly after the above lines:
-->"We found him with his face down in the pillow\\
With a note that said, 'I'll love her 'til I die.'"
** Also affecting could be these lines:
-->"We found her with her face down in the pillow\\
Clinging to his picture for dear life\\
We laid her next to him beneath the willow\\
While the angels sang a whiskey lullaby."
* "Waitin' On A Woman". A young guy waits on his girlfriend/wife(?) in a mall, and sits down next to an old man who tells him about all the times he's had to wait on his wife over the years. It was worth it.
** It is made even more of a Tear Jerker with the video. They have Andy Griffith speak the lyrics in and out through the entire song. This is especially sweet and tear worthy when Andy is [[spoiler: sitting on a bench in Heaven]] saying, "Honey, take your time, 'cause I don't mind... waiting on a woman." It might be far better than having Brad Paisley sing it. And even moreso yet after Andy died in July 2012.
* "You'll Never Leave Harlan Alive" (written by Darrell Scott) is basically a dirge about those who have lived and died in eastern Kentucky. In other words, it a ballad about getting out of a hellhole -- and falling back in again.
-->"Where the sun comes up about ten in the morning\\
And the sun comes down about three in the day\\
And you fill your cup with whatever bitter brew you're drinking\\
And you spend your life digging coal from the bottom of your grave."
* "[[ A Man Don't Have to Die]]" will cause ManlyTears to well up in its account of unemployment, divorce and alcoholism.
* "Letter to Me" can make one weep like a child.
* "He Didn't Have to Be", an utterly heartwarming tearjerker about the singer reflecting back on his relationship with his stepfather and looking forward to his own journey into parenthood, hoping that he's "at least half the man [his stepfather] didn't have to be".
* "Tin Can On a String," about a man who hears the church bells from the love of his life getting married to someone else and imaginging what life with her could have been like. A recording of an actual human heartbeat is used to accompany one of the prechoruses.