A playlist curation series. Each playlist includes written commentary on the theme as it relates to each song. If you have any questions/comments, you can email here.





One of my first playlists I made on my beloved iPod nano was titled “Songs to cry to.” When I remembered that I was like, “ok, that’s pretty cringe” but actually what I’ve found out is that I’m not alone! My favorite part of playlists is that they can act as time capsules or journal entries, they're entirely personal and contextual— you might listen to different things based on emotion, or time period, or where you live. For example, this playlist my friend Justus made for when your roommate is going through some shit circa 2015. As a side note Justus is super cool and smart and you should hire him; you can check out his brand new IMDb here.

This playlist is a sampling of my own personal favorite sad songs from a variety of genres and decades. By no means is it complete (obviously) since there’s only 10 songs, but it’s meant to be a well-rounded flight of melancholy tunes. Feel free to send any sad playlists you’ve made, I can share them here to provide a more complete picture of sad music, or I can listen to them alone in my bedroom and cry!




1. Moon Song by Phoebe Bridgers

This is an instant classic for alt kids in their 20's (me). I’m always disarmed by how vulnerable Bridgers’ lyrics and vocal performance feel. This feels like someone telling me a story they’ve never told anyone.

    "You are sick, and you're married
    And you might be dying
    But you're holding me like water in your hands"

Reminds me that at my most vulnerable, I cling to things that bring me comfort. Which makes me sad whether that comfort is healthy or not; it makes me angry at myself for holding onto things I should let go of but can’t, and it makes me feel so moved to know that lots of the comfort in my life is a result of supportive friendships and habits I’ve worked hard at developing. This is a strong start. I’m feeling confident.

2. Futura Free by Frank Ocean

Ryan Breaux’s interview at the end of this song made me break down today. He’s a snapshot of young joy and love, he reminds me of my own little brother. His recent death made me disproportionally sad compared to the many deaths I hear about every day. I've been wondering why; is it because the tragedy of his death stood in juxtaposition to the joy in this interview, the only thing I know about him? Or was it because I saw my own brother in him, that I think I can relate to what his family might be feeling? Maybe there’s not one reason. It’s just so sad. “sometimes I feel like a god but I’m not a god” is one of my favorite lines in any song.

3. I Don’t Smoke by Mitski

This one’s a sing-along:

    "if your hands need to break
    more than trickets in your room
    you can lean on my arm
    as you break my heart"

To me, this is a similar feeling to listening to Phoebe Bridgers in that the lyrics admit these feelings of complete devotion to someone or something, a recognition of how vulnerable we can become when consumed by love of any kind. This leo szn I’m thinking about self-love, and how I can admit and work on weaknesses of mine while still loving and nurturing myself. I’ve been thinking about the many people and ideas I love, and how I’m able to critique them and love them completely at the same time. When I listen to this song, I offer myself my own heart to break. (lol) This is getting a little emo and corny. But what else would make sense for this playlist.

4. Half-Light (feat. Kelly Zutrau) by Rostam

This song makes me want to laugh and cry at the same time, the heartbreaking intro is so sparse and intimate, and the instrumentals build and build to sweep me up off my feet—sometimes I literally laugh out loud because it makes me feel so happy. It feels close to musical theatre to me, like the most dramatic version of some kind of sadness I feel. I think that makes whatever pain I’m feeling seem part of some long human drama, the play of life or something. Maybe that’s part of the urge to relate to anything or anyone, that you feel part of something larger and, as a result, feel less alone.

5. A Case of You by Joni Mitchell

My mom showed me the Joni Mitchell album Blue when we were driving a lot together for college visits, and this is my favorite song from that album. It was one of the first times I remember thinking of her as a person in her own right rather than my mom. Very Lady Bird (2017) vibes. To paraphrase my friend’s review of Lady Bird, that movie wasn’t my favorite but I did still cry at the end. The album Blue functionally served as my complete crying playlist from the years of, like, 2012-2014.

6. I Can’t Make You Love Me by Bonnie Raitt

I used to play this all the time at the cafe I worked at in Boston but at, like, 7am lol. The chorus is like coming to terms with a dynamic in, for example, I Don’t Smoke; there’s an acceptance that however much you love or devote your energy to something, it still may not work out. There’s a great Bon Iver cover of this song, too. I designate this one a sing-along song also.

7. Killing Me Softly With His Song by Roberta Flack

I usually listen to this song with a glass of wine in one hand kinda swaying back and forth in the living room. I’d call it lush. Flack’s vocals cast a spell over me, her voice feels grounded and calm but filled with subtle emotional movements that make the whole song feel elegant and smooth and full of despair at the same time. In some ways I think of this as a happy song, it’s more upbeat than some of the others I’ve listed. But I think basically it’s a sad song, or a longing song at least. Either way, it’s a classic that I think is under-appreciated sometimes!

8. Something to Believe by Weyes Blood

Similar to Rostam songs, I expect most Weyes Blood songs to build to some majestic, orchestral swell. Bringing to mind Linda Perhacs and Kate Bush, this whole album feels intricately crafted, vibrant, and ethereal. Mering’s vocals in this specific song also bring to mind The Carpenters. In an NPR interview with Ari Shapiro, Mering talked a little about this song as it related to her Christian upbringing:

“I am somebody who feels a bit of a void there from having, you know, had that be such a big part of my life. I think, yeah, once you kind of have that structure within your mind, you would like to fill it with something else.”

I think my listening to this song is a little self-indulgent in some ways. Like Half-Light or I Can’t Make You Love Me, I’m listening to it to remind myself that my pain or sadness isn’t unique, that I’m feeling bad in pretty much the same way as everyone feels bad. Like those songs, too, Something to Believe feels so anthemic that it’s almost theatrical. Check out her new album with Tim Heidecker of Tim & Eric, the video for their song “Fear of Death” is out now and I love it.

9. J’attendrai by Rina Ketty

I like listening to this when I’m not sad so much as melancholy. It’s nice on rainy days or when I’m walking in the fall or something. I don’t know what makes me associate so many French songs with sadness, like I get that lots of people have a similar association, but why? Who told me that? Maybe it’s because my parents had Le ballon rouge (1956) on VHS and I’d watch it over and over. Or the Madeleine CD-rom I’d get to play when it was raining.

I think overall there’s this conflation of all things French with “sophistication” which I think is a dangerous capitalist idea. Like, I think the positioning of French art as really exceptional often has more to do with their general status as a colonizing nation than merit. Which isn’t to say I don’t like French art! I just think I should investigate why I’m drawn to things. I don’t know. I still listen to it when I’m sad and associate it with being sad so I’ll keep it on the list.

10. Married Life by Michael Giacchino (from the Up soundtrack)

If you haven’t seen Up then this probably isn’t great for the list. The melody is more playful or thoughtful than sad, I think. But every time I start this movie I have to pause 10 minutes in because I’m crying so hard. Now this song moves me to tears by association, I guess. It reminds me how close the sensations of love and grief are, and how expansive and life-changing both can be.