Outsider Picks: Sad Songs for Valentine’s Day

by Clayton Edwards
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Let’s face it, not everyone is having a happy Valentine’s Day. Love is a fickle thing and, if you’re not careful, it can slip right through your fingers. Being lonesome and heartbroken is hard any day of the year. However, Valentine’s Day might be the worst day for it. Everywhere you look, you see happy couples doing happy couple things. Social media is just awash with people sharing their warm fuzzy feelings, usually with love songs. Well, we know what it’s like. That’s why we put together a list of sad songs just for Valentine’s Day.

If you’re in need of a soundtrack for a sad Valentine’s Day head over to Spotify and check out Tear-Jerkers, Waltzes, and Other Lonesome Songs. It might not cure all your ills, but it’s just what the doctor ordered.

Select Songs from Our Sad Valentine’s Day Playlist

Now, I don’t expect you to just head over to Outsider‘s Spotify and jam this playlist without knowing what you’re going to get. Here are a few of my favorite sad songs from this Valentine’s Day playlist.

“Coming Down” – Lost Dog Street Band

This Valentine’s Day, start your sad song journey off with Lost Dog Street Band. This husband and wife duo has been making some of the most lonesome and heartbreaking music out there for over a decade. Benjamin Tod, the vocalist and principal songwriter for the group, spills all of his pain into Lost Dog’s songs. “Coming Down” is a perfect example of that.

The chorus will let you know what kind of mournful hard-luck tune this is. “And in my dreams, there’s a needle and a spoon. / Oh, there’s a pair of dice, a loaded gun, oh baby me and you. / And you’re sawin’ on a fiddle and I’m wonderin’ which to shoot. / Everything’s so complicated now I am comin’ down.”

“Jamestown Ferry” – Charley Crockett

If you’re freshly lonesome this Valentine’s Day, “Jamestown Ferry” is the perfect sad song for you. Several artists have recorded this Bobby Borchers and Mack Vickery co-write. However, Charley Crockett’s version is the go-to for Outsider staff. Crockett just has a way of making heartache sound good.

“The Grand Tour” – George Jones

George Jones was the master of sad songs, so we had to add him to this Valentine’s Day playlist. However, you won’t find “He Stopped Loving Her Today” on the list. That’s just too much sad when combined with the rest of the tracks. So, we went with what might be his second saddest song “The Grand Tour.”

“Diggin’ Up Bones” – Randy Travis

If you’re digging up memories of a long-gone love this Valentine’s Day let this sad song be your soundtrack. Randy Travis’ voice carries all the hurt that comes with walking down memory lane. Then again, it’s hard to be too sad when you’ve got Randy’s silky-smooth baritone in your ears.

“I’m So Lonesome I Could Cry” – Hank Williams

It doesn’t matter if it’s Valentine’s Day or not, this is the sad country song. No one moaned the blues like Hank Sr. and this is a stellar example of just how much hurt he could pack into his voice. Without Hank, the country music world wouldn’t be what it is today. Without whoever hurt him, we wouldn’t have this song.

Just keep that in mind if you’re suffering from a case of the blues today. It’ll get better one of these days and you’ll be happy for all the hurting you’re doing right now.

Listen to Tear-Jerkers, Waltzes, and Other Lonesome Songs

This is just the tip of the sad country song iceberg. Feel free to dig into the playlist below. While you’re there, follow Outsider on Spotify to get all the best music from our favorite artists.

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