I don’t know about you, but I don’t love going through breakups.
But I do love breakup songs. Specifically, I love the really sad ones. As an example, one time when I was in a happy relationship, Spotify decided to curate a “10 Years of Heartache” playlist and recommended it for me. And I listened to that playlist, which featured brutal heartbreakers like “Someone Like You” by Adele and “Someone you Loved” by Lewis Capaldi, for weeks.
Lucky for me, I guess, the past couple of months have given us some bangers that, dare I say, might go down as some of the best heartbreak songs ever.
First, there was Taylor Swift’s rereleased version of “Fearless,” which took me, at 28, right back to being a kid who had never been in love but felt gutted by the idea of love being lost. It wasn’t just me. There was a whole TikTok trend about happily partnered people listening to “Fearless (Taylor’s Version)” and suddenly reverting to their teenage ways of coping with relationship drama.
Even if you’re having a great day, your day is going to get gray if you listen to “You’re Not Sorry (Taylor’s Version)” or “Forever and Always (Taylor’s Version).”
A couple of months later, the sad bop gods gave us another gift. Yes, I’m talking about Olivia Rodrigo, the pop sensation you’ve by now probably heard or seen somewhere because she’s been popping up everywhere. She’s the reason people way older than 16 are getting all weepy about driving around alone for the first time. As soon as her hit “Drivers License” came out this year, it was deemed the song of the year.
It was the subject of a wonderful “Saturday Night Live” skit and 18-year-old Rodrigo later belted her hit as a musical guest on the show.
Lucky for me (again), Rodrigo is a huge fan and protege of Swift. So the younger singer’s music is a dream for a Swiftie who appreciates sad songs. In her debut hit and album, Rodrigo does what her idol has been doing for years: communicating via song emotions we’ve never been able to quite put in words. Whether you’re driving around the suburbs missing an ex and yelling about the red lights and stop signs, you feel that when you listen to Rodrigo sing about.
It makes me think of talking to Marcus Leonardo, who created The Emo Night Tour, which brilliantly capitalizes on people’s never-ending love for songs heavy in emotions. Recently, he and I briefly talked about why we might gravitate toward sad songs when we’re sad instead of, maybe, trying to cheer ourselves up with a happy song.
“When you’re going through something sad like a heartbreak, it feels good to feel like someone else has felt that,” he said. “It’s cathartic. You don’t feel so alone.”
In that spirit, I wanted to break down some of the newer heartbreak songs and why they’re so good at breaking our hearts in a way that has you, somehow, happily singing along.
“Favorite Crime” by Olivia Rodrigo
First up are two of my favorites on Rodrigo’s debut album, “Sour,” and neither of them are the aforementioned “Drivers License.” I’m all for Rodrigo’s catchy, angsty tunes like “Good 4 U” and “Deja Vu,” but hearing her softer side was a welcome surprise. On this one, she weaves a metaphorical tale of crime that could be a younger sister to Swift’s song “No Body, No Crime.” I haven’t been able to get it out of my head the way Rodrigo sings certain lyrics on this one.
“Traitor” by Olivia Rodrigo
Every now and then, I listen to a new song and it just completely takes me to another place. And then I listen to it 15 times in a row. This just doesn’t happen very often. But “Traitor” was one of those songs. It’s sad in all the ways perfect sad songs are. “It took you two weeks to go off and date her,” she sings. “Guess you didn’t cheat, but you’re still a traitor.” Ouchie.
“We Were Happy” by Taylor Swift
As as special treat to Swift’s re-recorded version of “Fearless,” the singer included on the album never-before-released songs she wrote during that era of her life. One of those was “We Were Happy,” and my first thought upon hearing it was: How has she kept this absolutely devastating and amazing song from us all these years?
“Without You” by the Kid Laroi and Miley Cyrus
It’s catchy! You can’t deny it. While it’s not exactly as tragically sad, it gets the heartbreak point across. Just like Halsey did with “Without Me,” this song expresses the simple sadness of going from being “with” someone to “without” them.
“Sorry isn’t Good Enough” by Joy Oladokun
Consider this your cue to listen to Oladokun’s new album. It includes this pointed breakup song about how words just don’t fix things.