Country music star Chris Stapleton is known for writing some real tear-jerkers. These three songs aren’t the only heartbreaking tunes that Stapleton has penned and produced, but they’re three songs that are more than worthy of a spot on this list. If you need a good cry, these saddest Chris Stapleton songs should do the job.
1. Fire Away, 2015
“Fire Away” is definitely one of Stapleton’s more haunting ballads, beautifully describing what it feels like to watch someone you love grapple with their inner demons and, in turn, become abusive towards the people the care about. “Honey, load up your questions / And pick up your sticks and your stones / And pretend I’m a shelter / For heartaches that don’t have a home” is a real punch to the gut.
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2. Cold, 2020
Stapleton manages to poignantly describe the despair of a breakup in “Cold” while still maintaining a good mainstream country sound. It’s an accessible tearjerker, one could say. “How am I supposed to live / When I built my life around you? / Try to put yourself in my shoes” are a few lines all of us could relate to when it comes to love lost.
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3. Either Way, 2017
We can’t have a list of the saddest Chris Stapleton songs without mentioning “Either Way”. The track describes the reality of a failing marriage, and Stapleton’s choice to strip down the song’s instrumentation to focus more on his voice is beautifully poetic. “It’s been so long since I’ve felt / Anything inside these walls / You can’t hate and you can’t hurt / When you don’t feel at all” is painfully relatable for those who have dealt with a broken marriage or divorce.
Photo by Terry Wyatt
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