10 Classic Sad Country Songs That Might Make You Cry 11Country music are songs that tell stories. Not all stories in country music are all about honky tonks, some are sad and talks about someone passing away. The following songs rank among the saddest country songs and demonstrate the range of emotions and themes songwriters have explored while grappling with mortality.

“The Funeral,” Hank Williams A.K.A. Luke the Drifter (1950)

One of the things that Hank Williams Sr. pioneered was the use of modern terminology to address death and other eternal matters. This song is Will Carleton poem about funeral of an African American child.

“Waiting ‘Round To Die,” Townes Van Zandt (1968)

Regardless of the genre, Zandt is considered as one of the greatest songwriters of his generation. He focused a lot on mortality and his saddest composition are from parental abuse to love gone bad, on an overburdened drifter.

“Letter to Heaven,” Dolly Parton (1970)

This song is about a naïve young girl wishing to send a letter to her deceased mother. After preparing a letter to God asking if she could see her mother again, the child gets struck and killed while taking it to the mailbox.

 “He Stopped Loving Her Today,” George Jones (1980)

In this song, the main character holds on to the memories of a lost love who doesn’t return until his funeral.

“Pancho and Lefty,” Willie Nelson and Merle Haggard (1983)

One of Townes Van Zandt’s most widely-covered compositions became modern-day murder ballad under the watch of two fellow outlaws.

“She Thinks His Name Was John,” Reba McEntire (1994)

Reba McEntire used her stardom to draw attention to the many lives lost to AIDS with this powerful single. The song tells of a woman who regrets all she’ll miss by dying young, all for a one-night stand with a stranger. Co-writer Sandy Knox wrote the song in part to pay tribute to her late brother.

“Goodbye Earl,” The Dixie Chicks (2000)

This macabre tale of black-eyed pea-flavored revenge remains one of the Dixie Chicks’ best-loved songs, and it’s at least their second best-known socio-political statement.

 “Concrete Angel,” Martina McBride (2001)

The lead character is a 7-year-old girl, beaten to death by an abusive mother after neighbors and a teacher ignore tell-tale signs of a serious abuse.

“Three Wooden Crosses,” Randy Travis (2002)

Travis’ country gospel classic ends with a surprising yet rewarding surprise. A farmer, a teacher, a preacher and a hooker are riding a bus struck by an 18-wheeler. Three of them pass away, with the song explaining the farmer and teacher’s lasting legacies. The narrative is then revealed to be part of a sermon, with the preacher holding up a blood-stained Bible from the accident. It’s not the same preacher from the wreck, as he ends up being the third victim. Instead, the hooker survived, keeping the deceased preacher’s Bible before giving it years later to her adult son, now a preacher himself.

“Sissy’s Song” Alan Jackson (2008)

Alan Jackson used his personal faith and Hall of Fame talent to pay tribute to former housekeeper Leslie “Sissy” Fitzgerald. She died in a May 20, 2007 from a motorcycle accident.

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