Chicago songwriter Jack Riedy is not standing still. Between releasing his debut album Raw Deal, organizing benefit covers for the Illinois Coalition for Immigrant & Refugee Rights (ICIRR), and playing at local venues with the Dealbreakers, alongside Adam Wisbrock on guitar, Mike Nick on bass and backing vocals, and Nate Hockenberry on drums, he is making his way through a DIY scene that thrives on human connection. His music lives in the details, pulling from everyday moments and turning them into something bigger, something shared. With a new single on the way and a growing circle of collaborators around him, I am excited I was able to catch Riedy at such an impactful time in his musical career.
You have had a busy stretch with radio sessions, benefit covers and new recording work. Does staying this active help keep you creatively sharp?
Yes, I try to keep a balanced musical diet. Playing live and recording both inform my songwriting. Seeing other bands is important to that too, I need to have fresh inputs.
Looking back at Raw Deal now that it has been out for a while, what still feels true to who you are as an artist, and what already feels like a snapshot of an earlier version of yourself?
I’m proud of all the songs on my first album. It took some agonizing to narrow it down to eight tracks, and they have interesting conversations when you sit them all in one place. My fears about markets mixed up with relationships are even more intense now that everyone has a casino in their pocket.
Raw Deal was entirely self-produced so the songs have only grown more potent after playing them live. I’m just getting started.
Your songs often zoom in on small moments and everyday conversations. What draws you to that kind of storytelling?
I’m fascinated by the way little phrases can be loaded with emotion. It’s the small moments that hold all our big feelings, like mealtimes and goodbyes. In any long-term relationship, you develop this shared lexicon of references and memories and gibberish. Today we’re so saturated by mass media that it feels like no one speaks exactly the same language, so when I come across a phrase that is filled with emotion I have to extract it.
Chicago’s DIY scene is very collaborative, I feel like I see a lot of the same bands and artists coming out and supporting other shows quite often. Who are some artists or bands right now that feel essential to what is happening locally?
Pinksqueeze is a killer indie rock band and they’ve put in lots of reps in college towns and street fests. I can’t wait for their next album, it’s going to be huge.
Wyatt Waddell is super talented. His new album The Understudy is one of the best of the year, pure AM radio soul gold.
The Chicago youth rock bands as chronicled by Eli Schmitt are exciting. I’m partial to Horsegirl, Current Union TM, and Joe Glass. I saw Joe’s album release show at the Bottle in January, and he played a great Replacements cover (and I say that as someone who also covers the Replacements).
Inés hasn’t released any music of her own but I would be the first to order a copy on vinyl if she does. She’s a fantastic house DJ, record collector, and party planner.Her sets are an instant mood booster.
You have worked as a writer and DJ in the scene as well as a performer. How has stepping into the spotlight changed the way you understand your own work?
For me, being a critic or a DJ is analytical. I enjoy researching and beatmatching and historical context and thinking and overthinking. In my own music, I try to get loose and follow my instincts.
How has the chemistry with the Dealbreakers evolved as you have played more shows and released more music together?
We’ve played together enough that we can try new things, like fills or solos or new tunes, and know that there’s a rock solid foundation. It’s like a great basketball team, we’re so locked in that I can no-look pass to where they’re going to be.
The new single sounds quite different than your past work. What pushed you to expand the sonic palette this time around?
I first wrote the main riff for “My Friends Were Right” in high school. It came to me during a test, and I had to draw sheet music on scratch paper to write it down so I wouldn’t forget it. I was into ska-punk as a kid and learned a lot about arranging from the intricate horn parts on Streetlight Manifesto songs.
The band and I have played the song live for a few years, so I wanted to capture that in a professional studio rather than track it in parts. Once I had Friends of Friends booked, I had to bring some friends along to play the riff on brass as intended.
What did working at Friends of Friends Recording unlock creatively that maybe was not there before?
It was a comfortable place to get down to business and conjure up a song. The furniture is nice, all the equipment is organized and easy to use, Brok’s dog Esther even hung around for moral support. Brok and his staff made it easy to just focus on creative decisions. I was surprised how quickly we were able to record, even with eight musicians.
When you are building a lineup or planning a show, how intentional are you about creating bills that reflect a shared community rather than just a similar sound?
I look at shows as ways to expand my community. I think a diversity of people leads to a variety of sounds, and vice versa. A good show has an arc. Chicago is a very segregated city, but people will visit new neighborhoods for the sake of live music. It’s an ancient ritual.
What venues, collectives or recurring nights have been important spaces for you to grow as a performer?
Burlington Bar is the bomb, and it’s built like a bomb shelter. Great place to grind out a set. I used to live right around the corner pre-pandemic, and I’m glad it endures.
You have seen the scene from multiple angles over time. What is something you think Chicago musicians do especially well when it comes to supporting each other?
Chicago musicians are open-minded, and they know that no one’s into just one thing. I think the purist genre snob has gone the way of the dodo. You can be in a punk band and have your folk acoustic side project. You can make crazy synth sounds on your laptop and find woodwind players to solo over it. It’s a musically omnivorous town. There’s a little audience for everything.
Collaboration can take a lot of forms, from shared members to recording spaces to informal networks. Where do you feel the strongest sense of creative exchange right now?
I never regret going out for a night of live music in Chicago. There’s so much music released everyday and so many other horrible things to be found online in isolation. It feels great to get out and engage with other people who care enough to hang around a dark room.
With new material rolling out this spring, are you thinking in terms of standalone singles or building toward a larger project?
I’m excited to put “My Friends Were Right” out into the world, including the remixes I cooked up.
The band and I have a few songs recorded with Evan of No Tagbacks. Come see us and you’ll hear them. (See you at Cole’s May 8th.) I’m working on some new tunes too. All part of the next album. Haven’t settled on a title yet…
As your sound continues to evolve, what new territory are you most excited to explore?
We’ve had a few sessions and performances with horns and keys from our friends in the Precious Metals, including on “My Friends Were Right,” but I’d love to do a full show with an expanded band. I first started writing music with horns so I like arranging those charts.
Beyond that, there’s always new rhythms. I want to write the world’s first footwork rock song. Nate is talented enough to pull it off.
How do you think Chicago has shaped your music, both on stage and within the scene?
I’ve absorbed so much from life in Chicago. If I can refract a little bit of that light in an interesting way, I’ll be happy.
Talking with Riedy, it becomes clear that his music is not built in isolation. It is shaped by packed rooms, late nights, and a constant exchange between artists who show up for each other. Whether he is expanding his sound with horns and keys or shouting out the next wave of Chicago bands, there is a clear throughline in his work: community first.
That momentum continues this week with the release of his new single “My Friends Were Right,” out May 1 on Bandcamp, with a compact disc preorder available now and shipping May 4. He will celebrate the release live on May 8 at Cole’s in Logan Square alongside Off Belay and Jack Moony and the Sun Drops, bringing the full energy of the Dealbreakers back into a room that thrives on it.
Stream ‘My Friends Were Right’ by Jack Riedy and the Dealbreakers now:
My Friends Were Right on Apple Music
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