Here Are the 21 Saddest Country Songs by Men, Ranked

Here Are the 21 Saddest Country Songs by Men, Ranked

Who says men don’t talk about their feelings?

These 21 all-time-great country songs by men are some of the most devastatingly sad songs that the genre has to offer.

Romantic heartbreak is a common theme in these sad songs, including classic breakup story songs from George Jones, George Strait, Alan Jackson and Trace Adkins.

These ballads are perfect tear-in-your-beer jukebox choices for when your love life turns south, and they’re also a master class in how to write an incredible, vividly relatable sad song.

But love gone bad is only one theme in this far-reaching list. The death of a loved one is another frequent topic.

Kenny Chesney and Cole Swindell both share heartbreaking stories of personal loss. But an album cut from Walker Hayes — written about his father’s decline — is perhaps the most haunting.

Read More: Here Are the 21 Saddest Country Songs by Women, Ranked

Brett Eldredge‘s “Raymond” shares the poignant story of a woman with Alzheimer’s, inspired in part by the artist’s grandmother, who suffered from the disease.

Another song on this list, Glen Campbell‘s “I’m Not Gonna Miss You,” also deals with the topic of Alzheimer’s — this time, written from the perspective of an artist who was diagnosed with it himself.

Several of the selections on this list aren’t just iconic sad songs. They’re also central to the country music canon.

One of the most important of those is Vince Gill’s “Go Rest High on That Mountain,” a song that Gill started writing after Keith Whitley‘s death in 1989. He wouldn’t finish the song until 1993, spurred by the death of his brother.

It’s become one of country music’s most frequently reached-for choices for funerals and memorial events, and Gill himself sang it at George Jones‘ funeral in 2013.

But “Go Rest High on That Mountain” clocks in at No. 2 on Taste of Country’s list of the saddest songs by men. Keep reading to see the devastating, late-in-life ballad by a songwriting giant that made our No. 1 slot.

Here Are the 21 Saddest Songs By Country Men, Ranked

Heartbreak, grief and sadness have been themes of some of the finest country songs of all time. Here is Taste of Country’s roundup of the saddest songs ever, sung in a male voice.

Gallery Credit: Carena Liptak

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