In preparation for my golden birthday on Nov. 27, I’m being That Girl and expounding my questionable knowledge upon you. Twenty seven years is a long time to live and learn – at least it feels like a long time – and so, without further blabbing, here are 27 of my favorite songs to play on repeat for hours when I feel really, really lonely, sad and melancholy. That’s healthy, right?
1. “If I Could Only Fly” by Blaze Foley – I happened upon this beautiful, simple song because I was being a creep and watching Tammy Wynette’s memorial service on YouTube. Merle Haggard sang this with just his guitar and I was stunned. Blaze Foley’s backstory is incredibly sad, which only makes this song more haunting.
2. “Pictures of Success” by Rilo Kiley – Top moping song for College Kara, hands down. I still relate to it.
3. “River” by Joni Mitchell – Sad Christmas 2014. And every year thereafter.
4. “Re: stacks” by Bon Iver – All of Bon Iver’s songs were the soundtrack to our formative college years. Each one sounds like the coldest part of winter.
5. “The House That Built Me” by Miranda Lambert – I still can’t make it through the part about “my favorite dog is buried in the yard” without crying.
6. “Has Anyone Ever Written Anything For You” by Stevie Nicks – Oh, Stevie.
7. “The Grand Tour” by George Jones – If Tammy Wynette is the First Lady of Sad Country (and she will forever be), the Possum is the President. “The Grand Tour” is the best country song about divorce.
8. “Casimir Pulaski Day” by Sufjan Stevens – Token weepie of our dorm days.
9. “Hurt” by Johnny Cash – This is my favorite music video of all time and after I read a Johnny biography last winter, I got really weird and played these Rick Rubin-produced albums for days while I took long, hot baths. I had a lot of time on my hands, OK? Elderly Johnny’s voice kills me.
10. “He Stopped Loving Her Today” by George Jones- One day I plan to sing this classic at karaoke and make all the old men at my hometown bar cry.
11. “I’m So Lonesome I Could Cry” by Hank Williams – The OG sad country crooner.
12. “Birds” by Neil Young – There were MANY Neil Young songs I could include, but “Birds” was my favorite sad song for a long time. “Feathers fall around you/and show you the way back home.”
13. “Blues Run the Game” by Jackson C. Frank – Besides being really beautiful and mournful, this song has a tragic backstory. Read about its writer here.
14. “Middle Cyclone” by Neko Case – Everyone needs love, even magical forces of nature like Neko Case.
15. “Famous Blue Raincoat” by Leonard Cohen – My last tragic relationship was like a Leonard Cohen song. After the breakup, me and Leonard had to take a little break; I couldn’t handle it. However, the two of us are back together and we are VERY miserable.
16. “I Can’t Make You Love Me” by Bonnie Raitt – The classic torch song. Bonnie’s version is the most gorgeous.
17. “Blue Eyes Crying in the Rain” by Willie Nelson – Everyone thinks of Willie as the classic stoner man, but I think his voice is one of the most heartbreaking I’ve ever heard.
18. “Til I Get it Right” by Tammy Wynette – MOST of Tammy’s songs are sad. She has tears in that famous voice. But this one, about falling in love and failing again and again, is the most eerily sad given Tammy’s tragic life.
19. “Easy From Now On” by Emmylou Harris – “There he goes/gone again/same old story’s gotta come to an end.” I prefer Miranda Lambert’s cover, but this song has long been my go-to breakup song.
20. “These Days” by Nico – It’s the most mournful, melancholy happy song ever.
21. “Stay” by Rihanna – It’s pop and it’s sad and it played on the radio a lot and sometimes I’d cry in my car, OK?
22. “Without You” by Lana Del Rey – I’ll let the queen of “sadcore” have a moment. I don’t find a lot of Lana’s songs to be Sad, but this one really is, especially the solo piano version.
23. “Alison” by Elvis Costello – “Alison/I know this world is killing you.” The prettiest girl at the party is usually the saddest.
24. “Hello in There” by John Prine – Master songwriter John Prine writes the saddest song in the entire world about a lonely elderly couple. This cry is on me.
25. “Crying” by Roy Orbison – Like Wynette, Roy Orbison has a cry in his voice. It’s contagious.
26. “So Far Away” by Carole King – Perfect for when you feel really lonely on a rainy day.
27. “Til I Can Make it On my Own” by Tammy Wynette – I have to end with the Queen of Sad, Tammy. Just go through a harrowing breakup? Play this. I promise it’s just what you need.
And because I love you sad weirdos, I put all of these on a Spotify playlist for you! Listen to it here.
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