Alan Jackson makes us cry even when he’s trying to be a nice guy.

“I’ll be the S.O.B. / If that’s what you need from me / So you don’t have to love me anymore,” he sang in 2011, and good golly, that’s heartbreaking.

“So You Don’t Have to Love Me Anymore” is just one of 12 sad Alan Jackson songs that make this list of his all-time most heartbreaking. Hits like “Drive (for Daddy Gene)” and “Remember When” have sold a lot of Kleenex. So too has “Where Were You When the World Stopped Turning,” Jackson’s September 11 tribute.

Dig a bit deeper to find devastating loss in “Blue Ridge Mountain Song,” a picker that seems to find its emotional depths during a heartbreaking third verse, only to see Jackson come back one more time to really turn his blade.

“The Older I Get” and “Bluebird” are two more lesser-known sad songs from Jackson’s catalog, while “Sissy’s Song” and “Monday Morning Church” are 21st century reminders of how he can drive a lyric home. “You left my heart as empty as a Monday morning church,” Jackson sings during this tragic song from What I Do.

Fans know the songs are key to Jackson’s Hall of Fame career, but he’s also had a secret weapon. This “intangible” is the focus of an episode of the Secret History of Country Music Podcast on Taste of Country and wherever you podcast.

Watch the video to enjoy all 12 sad-as-puppies-crying songs from country music’s King of Tears. Let us know your favorites, or any we missed in the comments section.

See Alan Jackson Through the Years: Country as All Get Out!