10 Saddest Songs Of 2020 That We Couldn’t Stop Listening To

2020 was, for many, a very sad year. At difficult times, many people turn to music for comfort and though it may seem counterintuitive, sad music is often the answer.

Sadness can make people feel isolated, and listening to a song that captures what they are feeling can be deeply cathartic. It can remind them that what they’re going through is universal, that there are so many people all over the world feeling the same way that they are. As such, they are not alone but are instead going through something very human and natural, something that others can relate to. Here are ten songs from 2020 to turn to the next time you’re feeling sad.

10 Phoebe Bridgers – Halloween

Just about any of the songs from Phoebe Bridgers’ second album, Punisher, could have made this list. This is an album full of heartbreaking lyrics, and there were plenty of strong contenders on the tracklisting. However, it’s hard to beat a song that opens with the lines “I hate living by the hospital/The sirens go all night.” “Halloween” is a song about wanting to escape reality (a sad world, a troubled relationship, a heavy past…) and become something new. The whole track is pervaded by the knowledge that, like the one afforded by putting on a Halloween costume, this transformation will be very temporary.

9 Mac Miller – Good News

“Good News” is an example of how a song can be transformed by its context. When Miller wrote it, he probably meant it to be a song about exhaustion and trying to be optimistic. However, Miller died in 2018, and “Good News” came out after his passing. Now, with his death looming in the background, Good News seems eerily prescient.

Lyrics like “I’m running out of gas, hardly anything left/Hope I make it home from work” sound like the words of a man who knows he doesn’t have much time. The final verse, beginning with the line “there’s a whole lot more waiting for me on the other side,” brings the track over the top. Miller’s death was almost certainly an accident, and yet lyrics like these make that knowledge hard to accept.

8 Bob Dylan – Black Rider

Speaking of death, there are several songs on Bob Dylan’s recent Rough and Rowdy Ways that deal with the subject. At this point, Dylan is 79. He’s been making music for nearly 60 years. It’s natural for him to be contemplating death. And yet, songs like “Black Rider” are a reminder that all of us have a limited time on this Earth, whether you’re a legendary singer/songwriter or not.

It’s hard to imagine a world without Bob Dylan. Because of the enormity of his influence, it seems like he’s always been there. “Black Rider” reminds the listener that he’s only human, and in turn, it reminds the listener of their own humanity.

7 Drive-By Truckers – Watching The Orange Clouds

The two albums released by Drive-By Truckers in 2020 were full of songs that spoke directly to the most powerful moments of the year. “Watching the Orange Clouds” takes the listener back to the Black Lives Matter protests that exploded after the death of George Floyd. Indeed, the song was written after singer/songwriter Patterson Hood returned from attending one such protest. The final refrain (“I’m just trying really hard to find a way/To make it all better”) speaks to what so many people were feeling at the time. Systemic racism has always been woven into the fabric of the United States and tackling it was a monumental challenge for these protesters to take on. Yet they continued to fight and endure, while so many sat at home watching and wishing for such courage.

6 Tim Heidecker – Fear Of Death

Comedian Tim Heidecker (of Tim and Eric) has been establishing a side career as a strong singer/songwriter. His latest album, Fear of Death, is what it sounds like: a concept album about confronting your mortality. The title track’s chorus (“Fear of death is keeping me alive”) is a sentiment many people can relate to in the age of COVID, and its opening line (“I live in fear of everyone”) recalls how it felt when we all began quarantining and wearing masks. Though he didn’t write the song or the album about the pandemic, Heidecker managed to tap into so many universal feelings here. His timing was perfect.

5 The Flaming Lips – Brother Eye

The Flaming Lips’ American Head is an album about growing into adolescence with a deep knowledge of death. It’s haunted by people from singer/songwriter Wayne Coyne’s past who passed away when he was young. “Brother Eye” is one of the album’s most touching moments because of the way it combines Wayne’s bittersweet nostalgia and love for his family with the passing of bandmate Steven Drozd’s brother. Coyne wrote the lyrics and Drozd sings them, and the emotions of both men combine into a track that is beautiful and harrowing all at once.

4 Soccer Mommy – Gray Light

Soccer Mommy’s Color Theory is yet another album that has plenty of songs that could be included here. However, its saddest moment may be its closing track, “Gray Light.” The track is about singer/songwriter Sophie Allison’s mother and her struggle with cancer. However, once again, the song means even more in the context of COVID. So many people watched loved ones get sick last year and had to stand by and hope that they would get better, that they would see them again. This song captures the feeling of watching someone endure pain and hoping that they will make it through.

3 Billie Eilish – No Time To Die

Though the new James Bond film of the same name was unfortunately but understandably delayed, Billie Eilish’s title track did see the light of day. It stands, alongside Adele’s theme to Skyfall, as one of the more acclaimed Bond themes in recent years. More importantly, the lyrics are pretty depressing. Billie really taps into Bond’s tragic dating history, how he is still reeling from the death of ex-girlfriend Vesper, and unanswered questions about his current love, Madeline.

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This song perfectly captures the feeling of doomed romance that haunts these recent entries in the series. Overflowing with feelings of mistrust, betrayal, and bitterness, the song is a grand expression of sadness that should tie into the movie’s themes beautifully (if it’s ever released).

2 Taylor Swift – Marjorie

Taylor Swift’s two surprise albums, recorded with indie rock luminaries like Aaron Dessner (The National) and Justin Vernon (Bon Iver), were both full of forlorn songs. “Marjorie” is actually reasonably uplifting compared to some of them.

It celebrates the life of Swift’s grandmother, opera singer Marjorie Finlay, and how much she meant to the loved ones she left behind. The song is sad because it’s about the passing of a beloved person, but touching in the way that their love for her helps to keep her memory alive. It’s a reminder that sadness can come with other emotions as well. Sad songs can make the listener depressed, but they can also make them nostalgic or contemplative, or even happy; as they can spark memories of wonderful things that have been lost.

1 The Microphones – Microphones In 2020

Like Marjorie, “Microphones in 2020” is a song that is both sad and hopeful. It’s a celebration of a life and a career, but it’s also about the weight of time. It’s not a song about dying, but about having to continue to live. Songwriter Phil Elvrum lost his wife to cancer, found new love, and went through a divorce, all while raising a young daughter. Now that he’s healing from the pain of those events he has to wonder: where do I go from here? It’s a question so many people will have to ask themselves as the events of 2020 that changed their lives become memories. Hopefully, readers can find some solace, and some help, in these songs and others like them, as they too begin taking steps towards their next chapter.

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