Top 15 Heartbreaking Indie/Alternative Albums to Listen to During the Winter

Here are the top 15 heartbreaking indie/alternative albums to listen to during the winter of recent years. These are in no particular order, but are perfect for capturing the odd feelings of loneliness that come in the winter time

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Max Kersteter, Featured Writer
November 30, 2021

  1. Be The Cowboy by Mitski          Japanese-American singer-songwriter Mitski is known for her songs about loneliness, longing, identity, and isolation, so it’s no surprise one of her albums, especially “Be The Cowboy” would end up on this list. Mitski wrote the album after not having enough money to fly home for the holidays, and with that came the longing for seeing her family. The song “Nobody”, off the album, is about a young woman grappling with isolation, and having a deep longing to have someone there with her, but she knows that nobody will come. “Old Friend” is a song about her trying to get back in contact with an ex, despite both of them having moved on with new people. There’s a yearning for when times were simpler for the both of them. Finally, there’s “Two Slow Dancers”, which is about two people at a school reunion, and how their lives have been lived since they’ve last seen each other, and a desire to just stay slow dancing in that school gymnasium forever, in each other’s presence, not having to be alone again.
  2. Melodrama by Lorde          “Melodrama” is a concept album about a house party, the events that lead up to it, and what happens after. “With a party, there’s that moment where a great song comes on and you’re ecstatic, and then there’s that moment later on where you’re alone in the bathroom, looking in the mirror, you don’t think you look good, and you start feeling horrible.” “It’s a record about being alone. The good parts and the bad parts,” Lorde told the New York Times. The song “Liability” talks about how she feels that due to her fame, she’ll eventually become a liability to everyone around her, that she’ll just be an emotionally taxing presence around them, or that people will get tired of her and just leave. Sober II (Melodrama) is about the aftermath of the party, how there’s this empty feeling when the lights are back on and you’re able to see the mess that was left, and how she’s left to clean it up herself. Then there’s “Writer in the Dark,” a song about how her ex cheated on her, and is basically a mockery of him in general. The lyrics “Bet you rue the day you kissed a writer in the dark” is referring to how she bets her ex regrets ever kissing her, or even going forward in a relationship with her.
  3. Psychopomp by Japanese Breakfast          “Psychopomp” is an album about love and the loss of lead singer Michelle Zauner’s mother. Zauner’s mother, as shown on the album cover, passed away due to cancer in 2014, and after her diagnosis, Zauner moved back to Oregon to be with her mom during her final months. After she passed, the band had started work on Psychopomp. The song “In Heaven” deals with the difficulties of moving on after the loss of a loved one, especially Michelle’s journey with it. “The dog’s confused, she just paces around all day. She’s sniffing at your empty room.” “Heft” is a song that discusses Zauner’s fear of “the same dark coming again,” that darkness being the grief of losing her mother and aunt to cancer. Despite this album having dark lyrics at times, the instrumentals are oddly poppy and bright, in contrast to the moody darkness of the lyrics, and are perfect if you just want to go for a walk in late November.
  4. Evermore by Taylor Swift          “Evermore” was released on December 11th, 2020, and just has pure, unfiltered, winter energy; most likely due to it’s acoustics and heavy use of the minor scale. “coney island” perfectly captures the feeling of visiting old hangout spots while the snow falls. It tells the story of two ex lovers talking about the nostalgia they feel for a relationship that fell out, “and it gets colder and colder, when the sun goes down.” “tis’ the damn season” is truly a holiday bummer. It talks about heading back to a small hometown for the holidays, just to meet up with someone from your past there, and chasing a relationship with them despite knowing it would be quick and fleeting. “Tis’ the damn season, we could call it even. You can call me “babe” for the weekend.”  Swift’s mastery of storytelling in her songs leads up to this storybook setting of love, memories, and a strong pull to your heartstrings. Probably a bunch of tissues, too.
  5. This Old Dog by Mac Demarco          “This Old Dog” is an album Demarco wrote to confront his conflicted feelings about his dad, who he never really got to know. Songs like “Watching Him Fade Away” and “Dreams From Yesterday” confront ideas of death, life, moving on, and whether Demarco could forgive his dad. “Moonlight on the River” is about grappling with knowing both of his parents had problems they just couldn’t figure out, but still feeling a weird sense of love for his mother. The light strumming of an acoustic guitar, along with the gentle synths help bring the story of a man looking at his past even more bittersweet and heartbreaking.
  6. Historian by Lucy Dacus          “Historian” isn’t just a story of loss, but it’s also about the way people carry each other and themselves through time. “Body to Flame” discusses the longing for things to go back to the way they were before a relationship (platonic or romantic) went bad. “Longing for your short hair to grow back to the way you like,” “I regret ever implying that you could be better.” The song “Timefighter” is a song about coming to peace about your own mortality, and how it’s a long and tiring road to get there. “Historian” has a wonderful blend of electric and acoustic guitars, harsh and mellower tones that are perfectly mixed. “Historian” has a narrative that is challenging the human condition, and the pondering of one’s own mortality.
  7. I’m Wide Awake, It’s Morning by Bright Eyes          “I’m Wide Awake, It’s Morning” is about frontman Conor Oberst’s time in the city that never sleeps, NYC. Although “First Day of My Life” has more of a first day of school vibe, the lyrics “Yeah, these things take forever, I especially am slow, but I realized that I need you and I wondered if I could come home,” perfectly captures the loneliness of living in a big city alone, with your apartment having one of the best views of all time, yet it’s empty. “We Are Nowhere, and it’s Now” tells the story of Oberst’s own struggle with the feeling of homesickness that comes with living far from home, and not knowing what to do with your life. “See stars that clear have been dead for years but the idea just lives on,” compares Oberst’s nostalgia to the light of dead stars, lingering in our sight for years, despite the moment they were alive having already passed. Oberst’s style of singing makes his music feel more like a conversation than a song, and it’s a conversation worth having.
  8. How to be a Human Being by Glass Animals          “How to be a Human Being” is an anthology of songs about different made-up characters, though some are inspired by stories they have been told during their 140+ concert tour. Although on the surface, “How to be a Human Being” comes off as an upbeat concept album, paying attention to the lyrics completely shifts the tone. “Youth” is the second track, and it’s told from the perspective of a mother who missed out on her son’s childhood due to not being the best mom. She talks about her unconditional love for her son, and how she wants him to feel as free, happy, and carefree as she wishes she could be. “The Other Side of Paradise” is the story of a man who sought out fame, leaving his lover behind to do so. The lover is the narrator, almost mocking him with lines of “Bye-bye, baby blue, I wish you could see the wicked truth,” and “I Settle for a ghost I never knew, super (Oh) paradise I held on to. but I settle for a ghost.” These characters are all featured on the cover of the album, and all have interesting and even haunting stories to tell.
  9. Folklore by Taylor Swift          It wouldn’t be fair if only one of the sister albums was on this list, so why not have both? “Folklore” has songs of love, acceptance, mourning, and heart shattering lyrics such as “and I can go anywhere I want, anywhere I want, just not home, and you can at my heart, go for blood, but you would still miss me in your bones,” from “my tears ricochet”, and “I’m still a believer, but I don’t know why, I’ve never been a natural, all I do is try, try, try.” These lyrics paired with the floaty, acoustic vibes of the instrumentals make for a perfect “I’m not leaving my room and I’m just gonna sit here and cry” type of day. Get ready, you’re gonna need tissues and an emotional support box of chocolates, because these songs are gonna make you wonder “Jeez, who hurt her so badly that she wrote THAT?”
  10. Boygenius by Boygenius          Boygenius is made up of three powerhouses; Phoebe Bridgers, Lucy Dacus, and Julien Baker. Although this is technically an EP, it deserves a spot on this list because of the mastery of the tone, lyrical geniusness, and haunting guitar riffs. “Me and My Dog” is a song about having a panic attack and wanting to escape the embarrassment that some people feel after having one, especially one that occurs around others. “I never said I’d be alright, just thought I could hold myself together; but I couldn’t breathe, I went outside, don’t know why I thought it’d be any better. But I’m fine now, it doesn’t matter.” “Souvenir” talks about an odd fascination of the morbid and dark, and about self loathing. “Always managed to move in right next to cemeteries and never far from a hospital, I don’t know what that tells you about me,” “When you cut a hole into my skull, do you hate what you see? Like I do?” The speaker is trying to open up about how they’ve felt so dark for so long to someone else, hoping that they wouldn’t be disgusted by what they see when they know the truth, and god, that hurts.
  11. You’re Gonna Miss it All by Modern Baseball          Modern Baseball’s “You’re Gonna Miss it All” is about Bren Lukens’ general feelings of teenage (technically early 20s) angst in college, with songs like “Fine, Great” which is about a toxic relationship where only one person gets to dump their emotions under the premise of calling to check in on the other person, “The Old Gospel” is about another relationship that is plunging to the rock bottom. Bren’s vocals hold a melancholic tone for the entire album, with hints of malice and regret. Their voice ties it all together, finally putting their emotions and regrets during that time to light in a beautifully dark portrait. Plus the album cover has an old family photo on it, so you know it’s gonna be good to spend the first few days of winter break listening to, staring out your window while doing it.
  12. A Moon Shaped Pool by Radiohead          “A Moon Shaped Pool” is one of Radiohead’s less talked about albums, and it is the most recently released, as of writing this. It’s the apocalypse, with it’s low humming chords, harsh noise, and Thom Yorke’s voice being soft yet firm, “A Moon Shaped Pool” is the act of going gentle into that goodnight. The universe ends with a whimper, and so does the last song on the album, “True Love Waits”. “Just don’t leave. Don’t leave.” are the last words on the album, and the words hit harder when you find out this album dropped a few months before the death of Yorke’s ex-wife, Rachel Owen, and the album was about the emotions Yorke felt during their split. It’s a truly haunting love letter to the person he was with for twenty three years.
  13. Carrie and Lowell by Sufjan Stevens          “Carrie and Lowell” is about Sufjan Stevens’ deceased mother, Carrie Stevens, but more specifically, her death. She died of stomach cancer, and struggled when Sufjan was a child. The songs explore childhood, family, grief, depression, loneliness, faith, rebirth, moving on, and grappling with how his mother left. “Fourth of July” is a song that discusses what he felt visiting his mother on her deathbed. “Tell me what did you learn from the Tillamook burn?” is referencing the Tillamook Forest, which was ravaged by wildfires between 1933 and 1951, and how beauty that you find in things like fireworks or forests is fleeting and brittle, and doesn’t last forever. Sufjan is telling himself, through the voice of his mother, that it’s time to let her go. Sufjan’s voice sounds as if he’s almost on the verge of tears this entire album, adding to the reality of his grief, making it one of the most emotionally packed albums in his discography.
  14. It’s All in Your Head by Dandelion Hands          Dandelion Hand’s lead vocalist, Kevin Morpurgo, doesn’t sing in all songs on this album, and that makes it more impactful. “How to Never Stop Being Sad.” is a song whose lyrics are just read out loud, like slam poetry. The song is literally a how-to guide in the most literal sense. The opening line “Repeat to yourself that they’re not really gone. Time has proven that fooling yourself into believing a lie is the most effective way to deal with things you have no control over,” depicts our speaker as someone who is dealing with the grief of losing someone. Whether they passed away, or the relationship fell out, the longing for those times back rings the same, no matter what. The closing lines of the song begs the listener to confront this monster that has taken over the things they used to love, ending the song on a hopeful note. “You don’t need other people to drive away your loneliness, you just needed to find a way to talk to it.” This album is talking directly to the listener, telling them that they aren’t alone in their loneliness or sadness, and that they just need to hold on and try to talk to it.
  15. Stranger in the Alps by Phoebe Bridgers          “Stranger in the Alps” is another album that has a childhood photo as the album cover, so get out your tissue boxes. The album discusses intimacy, documenting how our relationships affect the way we view ourselves and interact with others. It starts off with her reflecting on her relationships back when she was a teen, and ends the album with an odd fable from the POV of a murderer who is killed in prison titled “You Missed My Heart”, and an instrumental reprise of “Smoke Signals”, the first track on the album, which is a reflection about her relationship with Marshall Vore, but it’s presented in a way that feels like she’s talking about him at a funeral. Bridger’s excellence in songwriting shows it’s true colors. With her aching guitar strums and eerily comforting voice, “Stranger in the Alps” is a good song to listen to while driving in the winter, with it’s calming, yet heart shattering presence.