The Music or The Misery

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When High Fidelity was released in the spring of 2000, it quickly resonated with music lovers young and old, and though it would be hard to mitigate its initial success, I would argue the biggest impact the film has is with its cult following. Based on the 1995 novel by Nick Hornby, the film became something of a beacon for the aging music fan and a poignant examination of the dissolution of any relationship.


The Gen X classic is turning 21 this year. Fitting, since that is exactly the age its protagonist, Rob Gordon behaves when handling his break-ups. Still though, through all his misogyny, sporadic dickheaded-ness, and salty pretentious attitude, there is always something about Rob that is oddly likable. I’d like to think it’s his love of music. Loving music the way Rob loves music is really something to behold. It’s a pure kind of love that seeks to understand not only the music itself but yourself through the music.

Music is many things to Rob, a personality trait, a channel to be a condescending snob, and most certainly a device to express himself, but perhaps most effectively, music is how Rob Gordon connects with his audience, the one he consistently breaks the fourth wall to appeal to. The most compelling part of the film to me is when Rob is organizing his records and his colleague asks how he is organizing the collection. Without a trace of irony, Rob replies smugly with a sense of triumph: “autobiographical.”  This is how we hear music, through our own lives. There’s a reason the trope of a drunk girl dancing and belligerently yelling out, “This is my song!!” exists. It is her song - it’s also everyone’s song.

When we think about our own “Desert island, all-time, top-five most memorable breakups” we naturally think of the music that accompanied each of them. It’s like when you’re in the grocery store and hear “Nothing Compares 2 U” over the tinny speakers. Do you get the chills and start to choke up a bit - anyone? What about “Tangled Up in Blue?” “Case of You?” “It’s All Coming Back to Me Now?” There’s no way it’s just me.

The impact that a perfect break-up album has is often taken for granted in today’s musical landscape, where many people receive song recommendations from content platforms (more on that later), but the perfect breakup album? Man, it’s an art form in itself. It makes you remember all the good times while still painting your former flame in the harshest shades. It makes you wish you had never met them but can also make you feel grateful for having learned the tough lessons that couldn’t have been learned in any other way than heartbreak. 

Last year we saw the film's female-driven reboot of High Fidelity, a modern “revamped” approach starring ultimate cool-girl Zoë Kravitz. The cast and storylines are more diverse and well thought out in this iteration with BIPOC characters taking up space in previously white-dominated areas. We even see a gay love story that is independent of the other characters’ storylines altogether. Although the social climate may have changed, the personal connection to music as a life preserve during turmoil has remained. Zoe Kravitz's character Robyn Brooks faces the same challenges with love as Rob Gordon does. We still see the main character whine and moan about their break-up in a mostly honest way, and we still connect with them and their unwavering love of music all the more. 

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To celebrate the anniversary of the film we decided to curate our own “desert island top five most memorable break-up albums.” Our contributors range in age, sexuality, and life experience. Playlists have been created out of the ideal break-up songs from each album; they have given us their own personal experiences with their respective album choices.

Most people regardless of how obsessed they are with music have a break-up album or at the very least a break-up song. This is why the message of the movie stands the test of time, it’s because the impact of music is so universally felt.  Our protagonists show this as well; by the end of both the movie and the series, Rob and Robyn get over their respective music snobbery and go on to provide a platform for younger and upcoming artists. So what came first, the music or the misery? It’s the music my dude, it’s the music.


  1. Cher-  Heart of Stone
  2. Macy Gray - The Way
  3. AC/DC's - Highway To Hell
  4. Norah Jones - Come Away With Me
  5. Annie Lennox - Bare

I come from a long line of broken hearts. One of my first memories of my mother is her standing in the kitchen blasting Heart of Stone by Cher. It’s impossible for me to listen to it now without thinking of her. Of all the ways love has been cruel to her and of all the ways that particular genetic predisposition for heartbreak has been passed on to me.

I remember holding the cassette in my hands and being fascinated by the cover art. The painting of this wild haired beauty clutching a giant stone heart captivated me. It wouldn’t be until years later I would see the skull hiding in plain sight within that image. Which to me is exactly what love is all about; it will either be strong, powerful, and enduring, or it will fucking kill you. 


Each breakup I’ve ever gone through has felt like murder and as a serial monogamist, I’ve had my fair share. The older I get, the more I think about my first boyfriend and how maybe he was actually the perfect match for me. “If I Could Turn Back Time” inevitably takes me back to the night I ripped his heart apart and told him it was over. I will always remember the way the irises of his eyes flared with rage and pain. That moment has repeated itself in every breakup I’ve initiated since, and Cher has always been there to sing to me about regret. 

But don’t worry, Cher is also prepared for when you are on the other side of that equation. “You Wouldn’t Know Love” is about getting dumped and not being able to handle it. So you convince him to try again and worm your way back into his life only to break up with him a month later. Which at the time was absolutely reasonable until you look back and see that it was only ever about your deep, deep need to be in control. Or is that just a situation that is unique to me? 

Regardless of whether you are the broken hearted or the breaker of hearts, there will come a moment a week or two after it’s over where you can’t handle the emotional ride anymore. Where the pain of loss takes over your body and you catch yourself staring at the wall and welling up with tears. That moment is when the title track is ready to cradle you and tell you that everything hurts...and that’s okay. 

And maybe that was the feeling my mother was chasing when she was belting out every single tune on the album in the kitchen when I was younger. Not solace, not hope, just an acknowledgement that she wasn’t alone. The feelings of heartbreak are universal, and while they can be lonely we are never the only ones to feel it. From one brokenhearted soul to another I say this: Call your mother, or Cher, whichever number comes up first. 


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  1. Stevie Wonder - Talking Book 
  2. Nick Cave - The Boatman’s Call
  3. Al Green - Call Me
  4. Lou Reed - Transformer
  5. St. Vincent - MASSEDUCTION


The emotional cleansing of heartbreak is agonizing but restorative; it’s monotonous but pure. I once heard a Youtuber say (and I’m paraphrasing) that if you haven’t had your heart broken, I don’t know if I can trust you. His account has been deleted and I cannot recall his name, but I live by his words to this day. Stevie Wonder has a penchant for the transcendental and his 1972 masterpiece Talking Book is a spiritual journey of the wounded heart.

Some would consider this a reductive summarization— and they wouldn’t be wrong. Let’s be real, Stevie went off on this record and I don’t want to take that away from him, but Talking Book is inarguably the lamenting of Stevie’s collapsed marriage with Motown alumni Syretta Wright. The tears of its dissolution flow through the album’s runtime.

I think why this is such a great breakup record to me, someone who is reckoning with the year anniversary of his own cataclysmic breakup, is how deconstructive it is of the different components of heartbreak. “You Are the Sunshine of My Life” captures the nostalgia of lost love, reminiscing on the salad days where nothing could go wrong. Following it is the one-two punch up of what did go wrong: “Maybe Your Baby” exposes the jealousy and paranoia that can lead, and has led, to its demise. But as someone who has never been a “Jealous Guy” (hint hint), the almost 7-minute cut resonates in capturing the anxiety of knowing your past lover has moved on and that you’re still drudging in the debris of the fallout.


Speaking of drudging yourself through that debris, it’s hard not to talk about “Blame It on The Sun.” Blending the emotion of classic soul with the experimental nature of 70’s prog is what Stevie does best— he drags himself through the emotional gutter on this song in a way that only he could accomplish. The first time I heard it, I was brought to tears.


There is a light at the end of the tunnel though. That light is the gorgeous “I Believe...” No, its inclusion here is not merely due to its use in both screen variations of High Fidelity (though you have to admit, there’s something satisfying about the symmetry). I’m talking about it because it’s the sonic equivalent of a friend telling you, “You’re going to get through this,” sans the annoyance of feeling like they have no idea what the fuck they are talking about. It is beautiful and pure catharsis. If you’re dealing with a broken heart right now, listen. And please don’t hate me for saying it… but you’re going to get through this.

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  1. Kanye West - 808s & Heartbreaks 
  2. Noah and the Whale - First Days of Spring 
  3. Spanish Love Songs - Schmaltz 
  4. The National - Trouble Will Find Me  
  5. Sharon Van Etten - Are We There


When Kanye released 808s & Heartbreak in 2008, it didn’t land for me. I had come to expect a certain style of music from him and 808s wasn’t what I was hoping for. In part, because I had and still have a love/hate relationship with autotune, its heavy presence on the record coupled with the complete departure of what I had come to expect based on his body of work allowed me to quickly dismiss it entirely and put it back on the proverbial shelf for the foreseeable future. 

Roughly three years later in the summer of 2011, I finally got it. I had just experienced my first heartbreak and was spending the summer moping around in my basement bedroom depressed and in the dark. I was lost and having a hard time processing what I was going through, so as most do I turned to music. At the time, I was going through a Cudi kick and through the power of the Spotify algorithm, I was eventually brought to the aptly titled “Welcome to Heartbreak.” Through a combination of self-loathing, sadness, and laziness I decided to let the song play through instead of toggling my mouse to skip over it. By the end of the track I found myself intrigued and decided to give 808s & Heartbreak another chance.



What began as me casually listening to an album I never cared for quickly evolved to me hunched over my laptop intently listening to every word, simultaneously downloading and bookmarking every song. “Heartless” left me with a lump in my throat. “Paranoid” plays on the relatable tropes of a dysfunctional and painful relationship, while “Street Lights” explores the monotony of life when you're depressed and ends on a line I think every single person who's ever gone through a breakup utters at least once.

The auto-tune that originally pushed me away from the album in ‘08, I now found strangely relatable. My stance had always been that it was sort of like cheating, but now as I listened to Kanye belt out these painful lyrics about death and heartbreak, I couldn’t help but think he was using it to create some separation between himself and his words. Autotune provided him with the cloud cover to sing out those songs of loss and work through this pain without breaking down and eventually, his album provided me that same shelter to work through my first big breakup. 

Nine years later as I think back to that time in my life I can’t help but laugh a little about how sad I was, how much I thought I knew, and how I convinced myself I would never get over that person. With some hindsight I now realize it was never going to be the end of my world, but it’s like they say, you never forget your first and for that reason, Kanye West’s 808s & Heartbreak will forever be in my all-time top 5 breakup albums.

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  1. Fleetwood Mac - Rumours
  2. Amy Winehouse - Back to Black 
  3. Frank Ocean - Channel Orange 
  4. Bob Dylan - Blood on the Tracks 
  5. Alanis Morissette - Jagged Little Pill


I don’t think there’s a break-up album more iconic, more classic, more shove it in your ex’s face that you’re doing better without them than Rumours by Fleetwood Mac. I was 21 when this album came into my life in its entirety. Sure, it wasn’t the first time I had heard songs from Rumours; we’ve all grown up listening to our parent’s car music. I’d heard “Don’t Stop,” “Dreams,” and “Go Your Own Way” all half a dozen times in my life before I was 21, but what really brought the album home for me? A breakup.

I had been dating this guy for 6 months when the topic of meeting his parents came up. I didn’t think much of it, parents always loved me because of the “charming and lovable rascal” show I typically put on. Since we had never reached a definitive, we had a conversation shortly after; immediately things seemed distant and I can’t say I’m totally surprised things came to an end. What I can say I’m surprised at is how they came to an end. He broke up with me because his parents thought my life wasn’t going anywhere, and also the fact that I didn’t have or come from money didn’t help. How did I feel? Like someone just reached down into the pit of any self-worth I had left and gruesomely ripped it out for everyone to see. 

I went into work the next morning and after we all greeted each other one of my co-workers asked me what I got up to the night before. I told her and didn’t hold back on the details. I had to know that someone else thought the situation was as fucked up as I did. She stared back at me looking horrified, at a loss for words. She then gently put her hands on my shoulders and said, “Go home and listen to Rumours by Fleetwood Mac and you will know someone else has felt everything you’re feeling right now.”

I got on the subway and listened to the album front to back that day, the next week, and the following months. The iconic opener “Second Hand News” will always be memorable to me and not just because I sent it to my ex in an attempt to tell him how I felt (and to ruin his chances of ever being able to listen to the album without thinking of me). Who doesn’t love “The Chain” and its angsty defamation of former love?  My ultimate favourite though is “Silver Springs,” a song not included on original pressings, but whose reputation justified placement on the albums reissue. When Stevie sings “I know I could have loved you, but you would not let me,” it always gutted me. 



I don’t think it’s right to talk about the legacy of Rumours without mentioning its late resurgence via Ocean Spray and a Gen Z content platform. 'With ”Dreams” charting on the Hot 100 For the first time since 1977 last fall, it gave the internet hope that maybe 2020 hadn’t been a total loss. When I think of “Dreams” I think of Stevie’s candor on love and loneliness, and the internal anguish most of us can relate to. Rumours so perfectly encapsulates what it is to be loved and to feel loss; much of this can be attributed to the fact that it was famously written by people who were going through these very motions. So when I think of my top 5 all-time-desert-island-most-memorable-breakup-album? It’s unquestionably Rumours

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  1. The Cure’s - Disintegration
  2. Bruce Springsteen - Tunnel of Love
  3. The Gaslight Anthem - Get Hurt
  4. Ryan Adams - Prisoner
  5. Miranda Lambert - The Weight of These Wings


Why is Disintegration the ultimate break up album? Because it’s the musical equivalent of Mike Nichol’s 1966 film Who’s Afraid of Virginia Woolf.. Although the album is not a visual examination of singer-songwriter Robert Smith’s marriage disintegrating (which it didn’t), it does in fact capture a moment in time in which an artist and his band are struggling to determine their way forward, aware that there will be some casualties along the way. As an audience, we can appreciate The Cure’s ascent from their more minimalist, but profoundly dark releases like Faith and Pornography to their pop realizations like The Head on the Door and Kiss Me, Kiss Me, Kiss Me.  But Disintegration is something entirely different. There are no obvious singles, and while “Lovesong” is certainly a sensible choice and a thematic outlier, it is also a departure from what is otherwise an album devoted to the breakdown of a relationship. The fact that the relationship in question has more to do with the dynamics of the band are irrelevant: this is an album built around the idea of human connection disintegrating. It is grand in scale, weighing in at just shy of an hour and a half. It incorporates the standard Cure instruments – sharply defined guitars, heavy basslines, rhythmic percussion, layered vocals, and cinematic synths – but then elevates these usual elements beyond the Goth misnomer to something ethereal (check out the finish to Prayers for Rain, just before it transitions into The Same Deep Water as You) to suggest something that instead taps into the very human condition itself. 

It was the summer of 1989 and I was backpacking through Europe with friends when I had the opportunity to see The Cure touring their new album, Disintegration in an old Roman coliseum in Arles. I was listening to the album on my Walkman every day leading up to the show, but I was also falling in love with a beautiful young French girl I’d met in Marseilles through friends. We spent a lot of time together, her helping me practice my French while I helped her with her English. She agreed to come to the concert with me, and it was one of the best gigs I’ve ever seen. But I knew too when the band left the stage that we’d be going in different directions as well. Ultimately, that album soundtracked the most devastating romantic break up of my young life, but Robert Smith’s lyrics also taught me an emotional language I’d never before understood.


Who are we without the people that we think make our lives meaningful? If you’re in an intimate relationship, or interconnected with people in a band that defines your very existence (and let’s be honest, is there really a difference?), then how the hell do we move forward when our visions about the future start to diverge? Disintegration addresses those very dark-night-of-the-soul ponderings, and will provide you not just with worst case scenario examples (the title track), but also with, ironically early on, a sense of hope (“Pictures of Yous”).


So why is this the ultimate breakup record? Because in 1989, when the decade was coming to an end and everyone felt like an era of pop music, Polo shirts, VW Cabriolets, and geopolitical military stockpiling were coming to an end, The Cure’s Disintegration stood out as a beacon of everything suddenly stopping short, forcing us to distinguish what might come next in the new decade. Maybe what we listened to and loved wasn’t as dubious as we thought, and maybe the person dancing next to us wasn’t as questionable as they seemed an hour ago? Or maybe that it was a time and a place as Smith suggests at the album’s end, in which there’s no need to ever “dream of you again”. This is the ultimate break from both the past and who we thought we were then, as opposed to who we think we are now. And isn’t it nice to know that when your world comes crashing down, you aren’t actually all alone after all?



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By:

Kayla Vickers

Photo Credit:

3/26/2021 1:01 AM