Shorter Days & Sadder Songs: What to Listen to this Fall
Every year, musicians compete for one of the greatest honors in entertainment: the “Song of the Summer.” It’s a somewhat abstract title, measuring popularity by the likes of radio plays and club remixes. For example, nothing quite matched the complete domination of Sabrina Carpenter’s “Espresso” in the summer of 2024. It’s a just-cheesy-enough bop that’s easy to envision on repeat at a beachside cabana or an ice cream shop. But not all of us are built for the heat, and every popsicle must eventually melt. Some of us are simply meant to embrace the foliage of fall and the cold gray rain of an approaching winter. Rather than confidence and nonchalance, autumn is a time for seasonal depression and melancholy.
Some songs are already on every fall playlist—see “Sweater Weather” by The Neighbourhood, “Fade Into You” by Mazzy Star, or “Linger” by The Cranberries. If you’re already in the deep end of seasonal depression, skip right ahead to those classics. But if you’re still holding on to summer, I’m here to hold your hand while you walk into the shallow end. So here are the best (sad) songs for the fall – ideal for wallowing in your unrequited crushes and oversized sweaters – based on your Song(s) of the Summer.
IF YOU LOVED: “Fortnight (feat. Post Malone)” → “All Too Well (Sad Girl Autumn Version) – Recorded at Long Pond Studios”, Taylor Swift
We must, of course, start this list with an homage to Taylor. “Fortnight (feat. Post Malone)” was MTV’s pick for Song of the Summer at the VMAs, but any real fan knows that Swift’s autumnal ties are much tighter. She practically invented the entire season of fall when she released RED on October 22, 2012—before then it went straight from “august” right “Back to December”. She then revolutionized the season again by re-releasing the album as Red (Taylor’s Version) in November of 2021. Those nostalgic classics are the prime hunting ground for the perfect song of sad girl fall, and there are lots of excellent candidates but the winner has to be “All Too Well”. It was heartbreaking enough when it was only 5 minutes long, and then she had to double it and give us an acoustic, upstate twist. Just be careful – if you listen to “All Too Well (Sad Girl Autumn Version) – Recorded at Long Pond Studios” on a loop for the next three months, you might go from Sad Girl Autumn to Psychiatric Hospital Winter.
IF YOU LOVED: Short n’ Sweet → “how many things”, Sabrina Carpenter
At this point, it’s undeniable that Sabrina Carpenter kept the summer of 2024 “wrapped ‘round [her] finger” and under her comically massive heel. Her fame skyrocketed with “Espresso” and “Please, Please, Please”, and her new album Short n’ Sweet has plenty more bangers bursting with confidence and sex appeal. So to cut to Carpenter’s core, we have to go back in time a bit to her previous album: emails i can’t send. Maybe she had a dramatic change of character, or maybe it’s just impossible to feel depressed after opening on the Eras Tour. Either way, emails is where true sad girls will find their fall anthems. Specifically, “how many things” will make for the most effective seasonal transition. Its opening—“You used a fork once / it turns out forks are fuckin’ everywhere”—has just enough of the kind-of-dumb-but-kind-of-genius ring to it that “ me espresso” does; from then on, it’s a gut-punching rumination on loss and limerence.
IF YOU LOVED: F-1 Trillion → “Missin’ You Like This (feat. Luke Combs)”, Post Malone
I’m not sure anyone expected Post Malone to go country, much less to do it so well. His collaborations with Morgan Wallen (“I Had Some Help”) and Blake Shelton (“Pour Me A Drink”) topped charts and Song of the Summer lists through to September. Most of his new country collaborations are meant for having fun—pause here to listen to “Have The Heart (feat. Dolly Parton)”—but he does have a few for the sad girls to enjoy this fall. The best of these has to be “Missin’ You Like This (feat. Luke Combs)”. Both Malone and Combs have some heartbreakers in this one: “I thought the world would keep on turnin’ / no one told me it would stop” and “You’re the whiskey in my coffee / the unanswered in my prayers”, respectively. But its twang makes for an easy transition from this album’s standout singles, or even a certain “Bar Song” that set fire to the South this summer.
IF YOU LOVED: “Austin (Boots Stop Workin’)” → “Love Me Till August”, Dasha
One of the most divisive songs of the summer, some people thought that “Austin (Boots Stop Workin’)” by Dasha didn’t deserve the love it got. Those people are wrong – and could benefit from doing some research into ‘humor’, ‘country music’, or ‘serotonin’. “Austin” is a fun hit that leans into the campiness of country and makes the grumpiest New Yorker want to line dance. Though this is Dasha’s breakthrough, she is by no means new to the game. She’s got an excellent back catalog, and this longtime fan has the perfect recommendation for any new listeners: “Love Me Till August” walks through a pre-college breakup and might hurt in August, but it’s sure to hit even harder in the late-autumn slump.
IF YOU LOVED: Charm → “Alewife”, Clairo
There have been so many blockbuster albums released this past year that it might seem easy for Clairo’s Charm to slip through the cracks. However, those of us whose lives were practically endangered by the beauty of the two-single run that was “Sexy to Someone” and “Nomad” could never forget Clairo’s youngest project. This fall, revisit her debut album Immunity and sink into the sweet masterpiece that is “Alewife”. For true fans, take Amtrak from Penn Station to Boston’s South Station and the Red Line T from there to Alewife – it’ll take about 5 hours and cost a pretty penny but it’s worth it. If you aren’t willing to make that pilgrimage, lying on the ground and listening to “Alewife” on repeat might be the closest thing to enlightenment you can experience in the safety of your own home.
IF YOU LOVED: Men in touch with their feelings → “Halloween”, Noah Kahan
You may have experienced fall, but you can’t really *understand* autumn unless you’re from New England. And Noah Kahan is the absolute master of incorporating foliage into an audio file. “Halloween” is a hauntingly beautiful ode to mourning, memory, and the month of October. It’s hard to pick out a single line that won’t make you miss home, which really is what this time of the year is all about. This song—as well as most of Kahan’s discography—will fulfill any craving you might have for the soulful loverboy vibes of “Beautiful Things” by Benson Boone or “Belong Together” by Mark Ambor from this summer, all the way through what Kahan calls “Stick Season”.
IF YOU LOVED: Girly-pop pop → “From the Bottom of My Broken Heart”, Britney Spears
The summer of 2024 has seen the return of the pop star. If you fell in love with the public persona of Chappell Roan, the cheeky sex appeal of Sabrina Carpenter in Short n’ Sweet, or the world-conquering aesthetic of Brat, it may be time to revisit one of the most iconic pop divas of all time. After all, before there was “your favorite artist’s favorite artist”, there was simply: “Britney, bitch”. Many of Britney’s biggest hits came well after her debut album was released, and …Baby One More Time’s crown jewel is undeniably its title track, but “From the Bottom of My Broken Heart” is an underrated gem that offers a nostalgic shoulder for you to cry on when your spirits start to follow the downward trend of the temperatures.
IF YOU LOVED: Women (that’s it.) → “Robbed”, Rachel Chinouriri
No matter what you loved listening to this past summer, Rachel Chinouriri has it all. She’s got Sabrina Carpenter’s stunning vocals and sharp lyrics (as well as the opening slot on her upcoming European tour), Charli xcx’s gritty realism and English accent, and Tinashe’s refusal to conform to strict stereotypes the music industry tries to impose on young Black women. Her debut album What a Devastating Turn of Events was released earlier this year, and touches on all of the sonic seasons: “All I Ever Asked” clearly sounds best in spring, and “Never Need Me” has all of the catchy confidence necessary for summer. If you manage to get those two out of your head, take “Robbed” for a spin. It’s an elegantly simple story (“You were robbed of summer / I was robbed of you”) that cuts deeper than you might expect. For bonus points, check out the Spotify Singles version.
IF YOU LOVED: Chappell Roan → “California”, Chappell Roan
Chappell Roan has been unavoidable for most of 2024 (whether she likes it or not). Her album The Rise and Fall of a Midwest Princess started gaining remarkable traction in the spring, despite having been released months earlier in September—making it an autumnal album, mind you. Her newest single, “Good Luck, Babe!”, caused earthquakes while tracks like “Red Wine Supernova” and “HOT TO GO!” launched the album to the top of the charts. So while I’m tempted to give this spot on the list to another midwestern princess (like Ber, for “Superspreader”) or another queer songwriter who glitzed and glamoured her way out of conservative America (Allison Ponthier of “Hollywood Forever Cemetery”), it feels necessary to put some respect on the good name of Chappell Roan’s “California”. It’s a sort of love song to Missouri (though that may sound like an oxymoron) that will resonate with anyone who hails from a “dying town” and can’t live without four distinct seasons.
IF YOU LOVED: The Secret of Us → “Every Beginning Ends (feat. Benjamin Gibbard)”, Noah Cyrus
Sometimes a nepo baby is needed to save the day. Over the summer, Gracie Abrams came to the rescue with The Secret of Us, giving us warm-weather hits like “Risk” and “Close to You”. While Gracie leaves us to finish her run on the Eras Tour, Noah Cyrus is here to help us adjust to autumn. Even though her most popular song is called “July” (and that her sister Miley has been nominated for the VMA Song of the Summer award three times), this youngest Cyrus sibling is definitely familiar with fall. On “Every Beginning Ends”, she teams up with another autumnal expert: Benjamin Gibbard of Death Cab for Cutie (pause here to add “A Lack of Color” to your queue). Together they infuse the disparaging death of fall into the story of a relationship that grows old with time – although true sad girls will be able to apply this to any aspect of life: breakups, graduations, or finding out that your class crush is both gay and taken. And don’t worry, she won’t leave you hanging. After you wipe your tears, the rest of The Hardest Part can still provide a good fall soundtrack (particularly “Unfinished” and “I Burned LA Down”).
IF YOU LOVED: “BIRDS OF A FEATHER” → “Bloodbuzz Ohio”, The National
Honestly, you’d be hard-pressed to find a song by The National that doesn’t make you want to move to Maine and live on maple-sugar-pumpkin-something coffees forever. They’ve been pumping out music for their target audience of ‘sad dads’ since 2001, and have since cornered the market on making grown men with good taste cry. Their autumnal songs range from “Slow Show” (Boxer, 2007) to “Hornets” (Laugh Track, 2023), but the fall-est of the bunch has to be “Bloodbuzz Ohio”, from their 2010 album High Violet. Even if you’ve never gotten drunk and grappled with your thoughts on the state of Ohio like the song’s narrator does, you might find it complements your favorite songs from the summer. In addition to the hint of escapism that blends well with “Saturn” by SZA, the narrator’s “swarm of bees” mirrors Billie Eilish’s “BIRDS OF A FEATHER” in its laid-back alternative-pop vibe, providing lots of opportunity for ‘birds & the bees’ jokes.