sad songs

Definitely Gay: Sad Songs That Feel Good

Sad Sappy Sucker: Sad Songs That Will Make You Feel Better

I am a glutton for cathartic experiences, and music and movies are my preferred mediums. I think it’s fair to say the past year or so has been a bit…rough. When it gets to be too much, I have an ever-growing list of sad songs I like to listen to when I feel like throwing myself a pity party. These are some of my favorites. At the end of the article, you can find the full Spotify playlist.

1. Thinkin Bout You – Frank Ocean 

Figured I would get the most obvious sad song out of the way considering my column is called “Definitely Gay”, but who doesn’t remember their first gay sexual experience? I remember mine like it was yesterday, and when I first heard this song I felt like it was written for me.

2. You Look So Fine – Garbage

One common theme you will pick up on through these songs is unrequited love. This sad song has been relatable for me from high school crushes through today. What can I say, I’m predictable. 

3. You Don’t Know Me – Ray Charles

We were already on the subject of unrequited love, so might as well build on that. I would prefer to not dwell too much on how many times I’ve drowned my sorrows and blared this sad song. For those of you who have been “friend-zoned”, this is for you.

4. Modern Romance – Yeah Yeah Yeahs

Karen O is one of my favorite rock stars. Her energy is unparalleled, but I also love her when she’s in these stripped-down songs. “I was wrong, it never lasts, there is no modern romance.”

5. I Am Trying To Break Your Heart – Wilco

Jeff Tweedy knows how to write a god damn gut-punch of a sad song. It is difficult to find a better song befitting a disastrous breakup. It certainly makes me think of a specific one in my life.

6. Whenever You See Fit – Modest Mouse

I know 15-minute songs are not everyone’s jam (they are definitely mine). I usually like to listen to this one when I feel like my life is falling apart at a faster rate than normal.

7. I Can Never Be Myself When You’re Around – Chromatics 

I adore this band. I was OBSESSED with this sad song when it first released, and still am. Ruth Radlet’s dreamy vocals plus the musical genius of Johnny Jewel = perfection.

8. Wish You Called – Swan Lingo

In 2021, what could be more relatable than staring at your phone desperately waiting for it to go off? Throw in some moody 80s sounding synths and I am fucking in.

9. The Wolves (Act I and II) – Bon Iver

Justin Vernon is another incredible songwriter. This is one of his older tracks, and it deals with a breakup. It’s also used at the end of one of my very favorite films, The Place Beyond the Pines.

10. Wake – The Antlers

This is off 2009’s album Hospice, which tells the story of a hospice worker and the terminal patient he falls in love with. The album is a metaphor for an abusive relationship and the entire thing is depressing as fuck (and one of my top ten albums ever). All of the lyrics on this song are immaculate. It clocks in at 8 minutes but it is one of the most powerful on this list by far.

11. Putting The Dog To Sleep – The Antlers

This song is so deeply personal to me I can’t even bring myself to write about it, but trust me.

12. Forget – Twin Shadow

This was such a fantastic debut album, unfortunately, all the ones after just got progressively worse. The title track though has more of those moody synths that I am such a sucker for.

13. Me In 20 Years – Moses Sumney

This song is fucking immense. The way the music swells, the vocals, and the absolutely heart-wrenching lyrics. I implore you to find a better song to ugly cry to when it’s 3 am and your loneliness is crashing over you like a wave and you think you might drown.

14. Take Me Back – Deep Cuts

This song actually sounds almost upbeat and has some badass saxophone. But if you’re trying to get back with someone this a perfect sad song to blast in the car at night.

15. Coming Down – Dum Dum Girls

I’m still pissed Dum Dum Girls broke up. This is one of my favorite songs to listen to when I’m hungover and filled with regret from the night before. I think I might be melodramatic. 

16. Sometimes – My Bloody Valentine

Shoegaze is not everyone’s cup of tea, but it sure as hell is mine. I think it’s a fascinating genre. The music makes you really feel what the nearly unintelligible lyrics say. 1991’s Loveless is one of my top three albums of all time. This song is a definite highlight.

17. Fake Empire – The National

Honestly, I could use any song by The National, but this one is a favorite and I love some good horns (and Matt Berninger’s baritone vocals).  This sad song always makes me think of new love, but knowing in the back of your mind it has a shelf life. 

18. Nude – Radiohead

Once again, many contenders by Radiohead to make this list. I did go with this one because it’s been pretty heavy in my rotation lately. Plus, those lyrics.

19. Afterlife – Arcade Fire

Wow ok so I ALSO could have chosen a lot of songs by Arcade Fire for this list, but this one is really special to me. Lyrically, I think it is one of the best songs they’ve ever written. For bonus sad, watch the entire music video. I rarely can make it through without tearing up.

20. My Body Is A Cage – Arcade Fire

This sad song is haunting as hell, and even though I have been listening to it for 14 years I still get chills every single time at the 2-minute mark when the organs come in at full force. And don’t even get me started on those god damn lyrics.

That’s a wrap folks! I could have easily tripled the length of this list, but fear not! I have all of these songs plus plenty more on my Spotify playlist. I don’t always listen to sad songs and have been spending an inordinate amount of time working on playlists in general. Feel free to give me an add, and happy (or sad) listening!


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