Soundtracking Chicago: The Music That Shaped Me From The City I Love

This isn’t meant to be a deep article. Or even a particularly informative one, but it is heavy on nostalgia and cringey anecdotes—you’re welcome in advance. I was going through my Spotify playlists a few weeks ago, since I set the New Year’s resolution of making a new playlist each month (nothing makes you more insecure about your music taste than regularly updating it). All because I had a small existential crisis that I only listened to music made by people who are now dead and I am entirely out of touch with what the kids are listening to. But I know nobody else cares about this explanation so I’m gonna try to keep it brief, promise. 

To this day, the best playlist I think I’ve ever made is my first playlist, called “Red Arrow Hwy, Half Smilin” (clearly I was a curator of the ambiguously-titled playlist heavy on “vibes” from an early-ish age), from February 17, 2017. My obsession with Nico, Lou Reed, Van Morrison (so maybe I wasn’t so far off about the out-of-touch-with-the-music-of-today thing) and Father John Misty was reaching an obnoxious level. The playlist description reads, “if you don’t like harmonicas, you’re in for a long five hours,” which is sadly an accurate disclaimer. With the sheer amount of Bob Dylan, Simon & Garfunkel, The Mamas & The Papas, The Velvet Underground, The Doors, and Joni Mitchell featuring, the only logical explanation was that I must be making a movie about Woodstock.  Although it’s cringey in hindsight, every time I play that playlist now, it’s instantly comforting, like meeting up with an old friend. And I stand by most of those musical choices today.

But what this early attempt at music curation leaves out is how unequivocally shaped I was by the music coming up in Chicago when I was growing up there. It was a huge, nearly all-consuming part of my young-adulthood, and corresponded with the first time I ever snuck out of the house, my short-lived fake ID, the first time I ever smoked a cigarette, and the first time I ever got properly drunk. All meaningful milestones. Between Chance the Rapper, Noname, Mick Jenkins, Smino, Saba, Ravyn Lenae, and Towkio all releasing their first projects, 2013-2018 was a fucking exciting time to become interested in music.

So, I guess because I’ve never properly honored this period of my life via playlist or article, or maybe just because today I’m missing Chicago a little bit more than normal, I’m doing it now. Today I want to walk you through the Chicago musicians that soundtracked my adolescence, one album at a time. I wanted to limit this list to eight albums, but I’ve never been good at sticking to directions, so here are the eleven musical projects by the local legends who truly make me proud to be from Chicago. It goes without saying that there are so many more that could’ve been included here, but I carry these specific ones with me. Thanks for letting me share them with you. 

Album 1: Illinois (Come on Feel The Illinoise!) - Sufjan Stevens (2005). Listen here.

The best concept album I’ve ever heard. Sufjan Stevens is a genius who somehow makes state-themed albums featuring songs about prairie fires and John Wayne Gacy seem like the most interesting, thought-provoking musical content you’ve ever heard. Never have I felt prouder to be from the Midwest. I’m not joking. There’s something really, specifically gratifying about having someone else acknowledge what Pulaski Day is (to this day I’ve never heard of anyone outside of Chicago know what this is or celebrate it, even though public schools and libraries in Chicago close. It makes no sense). Honorable mention to his 2003 album Michigan as well if you really want to turn the Midwest appreciation up to ten, but I understand if that’s not for everyone. This was one of the first albums I bought on vinyl and I used to play it in my dorm room and cry when I missed home. There is something so expansive about Stevens’ musical arrangements that make you feel instantly transported elsewhere. No one makes music like him. 

Album 2: Acid Rap - Chance the Rapper (2013). Listen here. 

Acid Rap is a lot of things. It’s the first album I ever downloaded illegally off of the Internet, and thankfully still have, since “Juice” isn’t on the Spotify version of the album. It’s the first rap album I learned all the words too. It’s the album a boy played for me on the first date I ever went on. It’s the first album I can really say I loved when I was first developing my own musical taste. It’s a love letter to Chicago. I used to wait until my parents had gone to bed because we lived in an apartment that was not at all soundproofed, then I’d turn the lights in my room off, get into bed, and turn the album on, listening to the whole thing while I stared at the ceiling. That story is both cringey and incredibly embarrassing, but it’s unfortunately true. Fourteen was a really fun age for me, obviously. Although Coloring Book turned Chance into who he is today, Acid Rap will always be my favorite. I hope it’s the album people point to when they make a Chance documentary in thirty years as the moment Chance proved he was going to be huge. It certainly did that for me. It also taught me all the slang words for weed I’d ever need to know, and for that, I will always be grateful. 

Album 3: Wild Onion - Twin Peaks (2014). Listen here.

My first mosh pit experience happened at a Twin Peaks show at Lincoln Hall in Chicago in 2014. The guy in front of me spilled his entire beer down my shirt and it smelled so bad that when I came home my mom asked me if I was drunk. Twin Peaks was the height of softboi guitar culture, at least within my friend group, in Chicago in 2014-2016, and it’s wild to see them selling out shows and playing Austin City Limits and Lollapalooza now. One of my best friends and I used to go to their gigs together, and before each show we’d get drinks at Castle Liquors by the Thorndale red line stop next to my house because they didn’t card minors (and I think they still don’t—but you didn’t hear that from me). Musically, it’s like the perfect mix of garage rock that’s so loud you can’t really tell if it’s happy or angry, but it works both ways. They were the band I’d stay up all night to buy tickets for, and I still have the first band t-shirt I ever bought after one of their gigs. I’ve seen Twin Peaks live probably at least six times by now, and if I had to pick a specific album that encapsulated my first two years of high school, it would be Wild Onion. Making Breakfast is still such a banger.

Album 4: INNANETAPE - Vic Mensa (2013). Listen to most of it on Soundcloud here.

INNANETAPE was just before my time, but it’s such an intricately layered mixtape that it deserves a spot on this list. Vic Mensa came up with Chance and they used to collaborate on each other’s projects regularly. “Holy Holy,” featuring BJ the Chicago Kid and Ab-Soul, is probably the mixtape’s standout (in my opinion), although the whole thing is a masterclass in DIY hip-hop songwriting and production, and it’s well worth a listen.

Album 5: Telefone - Noname (2016). Listen here.

I think Telefone, along with Chance’s Coloring Book, are the two best hip-hop mixtapes (not albums, although I know that distinction can be murky) to come out in the last ten years. Honestly I do—and I stand by that—but the fact that Telefone has received so much less critical and commercial attention really speaks to how male-dominated hip-hop remains today. The first time I heard Telefone, I remember thinking that it was a body of work I’d keep returning to for the rest of my life. And I hope that remains true. It’s as good as anything Kanye’s ever released, or Kendrick, Frank Ocean, Brockhampton, or Sza. Noname writes the most socially conscious rap music being made today, and in a genre where ‘conscious rap’ often gets lost in the flashiness of the industry, this is no small thing. Noname’s meditations on gun violence, race, adolescence, and black womxnhood are arguably the most introspective hip-hop lyrics I’ve ever heard, and I hope she keeps making music for the next 70 years. She’s a legend in the making. 

Album 6: The College Dropout - Kanye West (2004). Listen here.

The beginning of an era. Although I’m sure its inclusion doesn’t surprise anyone, and love for Kanye (as well as criticism) extends far beyond Chicago, The College Dropout walked so Coloring Book could run, and every kid from Chicago loves Kanye, regardless of whether they want to admit it or not. Him and Chance are like two poles at opposite ends of the hip-hop spectrum musically and ideologically, which is why their collaborations and friendship are so interesting. The College Dropout is still far and away my favorite Kanye album, and “We Don’t Care” is far and away my favorite Kanye song. If he tweeted less and concentrated more on his music, we might eventually get another one of these gems. Till then, I hope living in Wyoming calms Kanye down.

Album 7: Light Upon the Lake - Whitney (2016) Listen here.

Pivoting to the softboi indie rock side of this spectrum, the musicians in Whitney are essentially the poster children for the Pitchfork Music Festival. After Smith Westerns (another incredible local Chicago band I’d include on this list if there was more time) dissolved, guitarist Max Kakacek, who looks like he could be the leading guy in yet another High Fidelity reboot, and Julien Ehrlich, the former drummer for Unknown Mortal Orchestra, who looks like he models for Carhartt, joined forces to start Whitney. There used to be a Twitter account called Chicago Band Boy that dragged absolutely every band in Chicago created in the Twin Peaks/Whitney mold (there’s a shit ton of them to be fair), and I remember them once tweeting “Mac Demarco’s new album is coming out this year and I’m so excited I cuffed my jeans to my knees,” and to me that encapsulates both Whitney and their fanbase. It’s hard to describe them without listening to them, so you should probably just do that. Lights Upon the Lake is a modern classic, and their cover of Allen Toussaint’s “Southern Nights” is surprisingly good. 

Album 8: Songs for Dads - The Walters (2014). Listen here.

Each one of the members of The Walters looks like a boy my mom would describe as ‘a very nice young man’ if I brought any of them home to meet her, and I’m not sure if that’s kinda cute or a massive turn-off. Although they also released the album Young Men in 2015, Songs for Dads, their 2014 EP, is the band’s standout release. It’s shoegazey indie-rock with some 50s doo-wop thrown in, and it’s a surprisingly successful combination. “I Love You So,” the lead single from the album, has somehow amassed 91 million streams on Spotify, which is wild, but my favorite song from the EP. “Fancy Shoes” seems like it should play in the getting-ready-before-the-first-date montage of a coming of age film. Or a life insurance commercial that features an old couple dancing. Or a really soft fan edit on TikTok. And I’m fine with any of those options. 

Album 9: Chicago Style - The O’Mys (2012). Listen here.

I’d include this album only for its nostalgic album cover which features two boys jumping into Lake Michigan in the summertime, but there are thankfully other reasons too. “The Wonder Years,” the album’s opening song that also features Chance the Rapper and Nico Segal, sounds to me like the perfect soundtrack to summer in the city. The O’Mys are mainstays in local Chicago music, and the duo combine the perfect blend of old school R&B and Soul instrumentation, and vocal arrangements with more modern production techniques, and plenty of hip-hop influence. They allegedly birthed the idea for The O’Mys at Kanye’s 2008 Lollapalooza set, so there’s that. Their follow-up album, Tomorrow from 2018, is also excellent, if you finish Chicago Style and still want more. 

Album 10: Next to The Sun - KAINA (2019). Listen here.

KAINA is a babe. The first song I heard of hers was “Honey,” from the 2016 EP Sweet Asl that she collaborated with Bedows and Burns Twins on, and the song features the sweetest melodies as well as a super unexpected horn section that make it one of the most relaxing songs I’ve ever heard. Next to The Sun is her debut album, released in 2019, and it sounds equal parts ethereal, but also kind of spooky at the same time. She’s also signed to Sooper, a local Chicago label which is putting out really exciting music right now. I listened to this album constantly when it came out in 2019 at the end of the summer, when I was moving into a new apartment and visited London for a few days on my own, and I really associate this music with that time in my life. She reminds me a bit of Jamila Woods (another amazing Chicago artist I’d include if this list was longer), and has the most beautiful, haunting voice. These songs definitely feel witchy. Spell-casting vibes for sure. 

Album 11: Flower of Devotion - Dehd (2020). Listen here.

Best for last! Dehd is my favorite band making music today. Hands down. Flower of Devotion was my most listened to album of 2020 and I recommend them to absolutely everyone I meet. If you’re reading this, that includes you too! Their frontwoman, Emily Kempf, is also a tattoo artist, (@magictatty on Instagram), who gave me my first tattoo this past July. I spent most of the time trying to play it cool about how much I liked her band while she was literally sitting in front of me tattooing my ribcage. Best day of my life. Anyone who claims to be a music fan should check out Dehd (even if you hate tattoos and fun tattoo-related anecdotes—although if you hate fun I don’t think we can be friends). In all seriousness though, you can’t go wrong with a single Dehd song, and their 2019 album Water and 2016 album Dehd are honestly just as good. They can’t put out a bad song.

Ok, I think that’s it for now. Thanks for letting me rant! I hope you got some new music recommendations, or maybe not. Either way, I had fun.