Interview: Jack Riedy Preps For a Busy Summer

It’s a busy summer for Jack Riedy. Between DJ sets and a show at Reggie’s on July 1, the Chicago rocker is celebrating the release of his catchy latest single, “My Friends Were Right,” a song that dates back to his high school days. We talked with Riedy about discovering Prince, the rewards of remixes, and why Chicago venues are so awesome.

How did you discover your love of music?

It's hard to even think of a first moment or anything like that. I grew up listening to music around the house all the time with my parents. I (grew up during) the age of having an extensive CD collection, so they're playing the same stuff around the house that they're bringing with them in the car when we're going places, and then they're buying CDs based on what they hear on the radio and stuff like that. So I grew up being exposed to my parents' pretty eclectic taste, and then coming of age with the internet, being able to explore even beyond that all this kind of music from all over the world, I feel like I grew up in a very good time to appreciate music in all sorts of forms.

I do remember very specifically one time being in the backseat of the car when I was probably nine or 10 years old and hearing the organ and the sound of church music and this sermon coming on that turns into this rock and roll freakout thing. I remember asking my parents, “What is this?” They're like, “Oh, you haven't heard this? This is Prince. This is ‘Let's Go Crazy.’” 

It happened to be very soon before he played the Super Bowl halftime show, and so then I was very wowed to see that on live international TV. So that was a real lightning bolt moment, at least for a very certain kind of music that I really enjoy. It's like finding out, oh, there's this guy who's been around for 20 years that even as a young music nerd I was pretty ignorant of, and here's some of his masterworks, and to see him still doing it was pretty incredible.

Speaking of Prince, you’ve even written a book about him, Electric Word Life.

Yeah, that was great. It was actually a collaboration between me and my now-wife, who's a visual fine artist, and so she did a bunch of the not only illustrations in between the stories and chapters of the book, but she also designed this really cool pattern for the outside of the book, and the physical book is shaped and designed like a seven-inch single with this very cool folding paper design, thanks to our collaborators at the Cereal Box Studio. It was a really great experience to not only put a bunch of different thoughts and stories and interviews and essays together about Prince and collect a bunch of different ideas in one place, but then have it packaged in this really cool-looking and incredible, unique style was a really special experience, so it was great to work on that together and bring it out into a limited run, publish it, and share it throughout Chicago. I know we were stocked at Quimby's and a bunch of other indie bookstores, and then we sold out our run of that, so it was a really great process to do independently, and frankly it was a good run for starting to put out my own music, too.

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Did you grow up in Chicago?

I grew up in the Northwest burbs, and then have lived in Chicago for the past 10 years, ever since I got out of college, so growing up I always was into music in general, thanks to things like WXRT and reading the Tribune record reviews, so I always had an idyllic vision of, ‘Great, I'm going to get out of school and live in Chicago, and then I'll be able to just go see cool bands all the time,’ and lo and behold, that is somewhat true for me, so I'm very lucky.

What was the first concert you ever saw?

I think the first show I would have seen that I have very fuzzy memories of was seeing They Might Be Giants when they played in some sort of summer fest or what have you at Lincoln Park Zoo. I was probably seven or eight years old, and I knew their music again from my parents' record collection, and really enjoyed being able to go see them. The first one that I remember hearing about and being like, ‘Hey, I should go to this show, we should make this happen,’ was a little bit later when I think I was in middle school. I went to see Weezer at the Allstate Arena, and that was a real, ‘Ok, cool, this is a band that's on a little bit bigger of a scale, they're bringing along openers that I hadn't heard of,’ and got me hip to some other styles of stuff, and that was real instructive too.

Speaking of They Might Be Giants, I listened to your debut album and my favorite song was “Your Timeline,” which sounds a lot like TMBG.

Thank you, I appreciate that. 

What went into the production and song selection on that debut album?

It was a really gratifying process, and I'm glad “Your Timeline” is one that really resonates with you, because that was the first song that I finished for the album, so that one in particular was really helpful to sort of kick the door open a little bit to, ‘I'm gonna finish one song, hey, I can finish a few more.’ And so the process for me was really gratifying to take a lot of different song ideas that I had kicking around, literally sitting in my iPhone notes folder and stuff, and spend the time actually turning them into something through recording on my own, and doing the production myself at home and recording most of the parts.

It really was a process, taking some songs and figuring out, okay, which of these have real legs to them, what can be a chorus or what can't, and then doing take after take to get things the way I wanted, or layering in additional instruments, or bringing in some friends to do some guest parts or solos and things like that. I almost looked at it as sort of a summary of all the music that I'd been into up until that point. 

I don't know who first said it, but they joke about, you know, when you do a debut album, you've got your whole life to work on it, and then after you put that out, you've got, I don't know, two years to do a sophomore album, and this album definitely feels that way for me. When I listen back to it, I can remember a lot of specific details that I remember working on and sort of carving into shape. I have specific memories tied with some of them, whether it's relationships, or things at work, or other parts of life that inspire different lyrics. So, for me, it feels like a real time capsule, even though it's only been out for about a year or so, and I'm very proud of it.

It definitely was a process, putting the songs together on my own, and then narrowing them down into the final eight that are there, but I'm really happy with them as a package, and it did really help to think of them as a unit, especially as I was fine-tuning some lyrics, and some vocal things, to think of how they kind of bounce off each other thematically.

Jack Riedy (Photo: Haley Gallinadelapena)

The album has a few remixes as bonus tracks. What makes you want to explore different variations of your work?

I think of it almost like a dessert, especially when I'm working on a song, and really starting things off, or kicking off a new idea. I think it's almost self-fulfilling for me, where if it's sticky, and I remember the idea, or it's got a little tune to it in my head, then I know it's got legs. I find it really gratifying to finish a project, and then it's almost like knocking over a LEGO project, and building something else out of it, where you're taking the chorus, or you're taking the drums, or the rhythm section, or who knows what you're holding on to, but kind of rebuilding something in a new shape, but with the same parts. 

I find that really gratifying, and especially with some of the music that I like to play most when I'm out DJing, or even when I'm just listening around the house, are some of the songs from the late 80s, early 90s, where there's this interesting intersection of rock bands and house music and hip-hop, where bands were starting to be remixed by DJs specifically for the dance floor, or bands were building songs from scratch off of drum samples in a way that they hadn't previously. I like trying to follow that process a few years, a few decades later on my own, on my laptop, and I think it helps me just approach ideas from a different way. It feels like practice, if nothing else. It's a rep, it's a way to get better at what I'm doing.

How did you find your way into the DJ realm?

That's something that I picked up a few years ago. I have to think about exactly when, but it actually started with a Prince event, where I was DJing at G-Man in Wrigleyville for the anniversary of 1999. I think it was turning 40 at the time, which is a really great album. It's one of my favorites. It's really one that's influential even amongst Prince albums for sonics and the drum machines in there. It's definitely one that's been influential on me, and I had written about it in the past, specifically its influence on Chicago house music, and a story for the Chicago Reader, where I interviewed a bunch of people who were teenagers at the time that became house music pioneers, and how he was influential in all these different ways, and how he then looped back around in the 90s to hiring some of these people to do remixes for him, and things like that. So I had this event planned where I was going to DJ a Prince set, and I had to learn how to DJ before the event rolled around.

I reached out to some friends of friends who were able to help me find a benevolent DJ to teach me some of the very basics on working two turntables and a mixer. Microphone usually not included, but hey, I'll do a little toasting if I can get one. So it was really just getting the practice in on a specific set of a specific artist, an era that helped to have those guidelines. It wasn't just, ‘Well, you can play all the music in the world in your DJ set, what do you want to do?’ So that was a really helpful way to practice. It's been something that I've been trying to get more reps on ever since.

I've been able to DJ at quite a few different bars and clubs throughout the city, which has been really fun. And in a similar way to working on my own music, I appreciate putting together a set and playing songs that seem to flow together and finding the commonality. A lot of the music that I like seems to all come back to one beat or another or one bass tone or another. So it's fun finding those little prominent gradients.

You talked about how Prince influenced some people in the Chicago scene. I’d love to know how Chicago has influenced you as an artist.

It's been super-inspiring. Part of what drew me to live here in the first place was the abundance of venues and bands and things like that. And then as I actually got involved in the scene and just saw how many opportunities there are and how much local talent there is, it was really gratifying to see a band like Beach Bunny that I was seeing when they were a DIY group and playing house shows and things like that. And now (Beach Bunny lead singer) Lili (Trifilio) is somewhat of an institution around here and booking her own festivals and all this super cool stuff. It's so great to see. 

Not that I am doing this to achieve the sort of material success that Beach Bunny or some of these other groups have, but it's just cool to know that there is an audience here locally for music that's made by people in their neighborhood. The beauty of Chicago with as many neighborhoods as there are is that people make music in every neighborhood and they cross neighborhoods to work on music together and to show it off. There's just so many different styles out here. It's hard for me to even begin with how Chicago's influenced me, but in particular, it's really made me feel like anyone can make music and communicate something through it in a worthwhile way. I'm very happy to be able to share the stage with a bunch of really talented bands and play at these venues that, in some cases, I've been going to for decades on my own.

What’s your favorite venue to play?

I've been really lucky so far in the history of my gigging with my band, the Dealbreakers, that we've played a lot of really great venues in Chicago and even some newer ones like Color Club. I think we had a really great time playing Cole’s in Logan Square just a few weeks ago. That's one that I really think of particularly fondly in my memories because when I first moved to Chicago, I was living in Logan Square and I'd spent a lot of time there seeing a lot of shows. Some of my lyrics are probably based on some nights out and memories from going to Cole’s and things like that. We had a really great show there.

We've got Reggie's coming up in early July. We're playing Reggie's Rock Club on July 1st with Rigid and Sattva Dog. So really excited to do a very heavier bill with this kind of legendary rock punk club that is one of our favorite venues. Every place we've played, my band and I have looked at each other like, ‘Wow, this place is great. This is awesome.’ And so shout out every place we've played. There's been variations on the nights that we're playing and the bills and the ability of hospitality they're able to offer and stuff like that, but everyone's been, baseline, really respectful and helpful and everyone's paid us the way they're supposed to. You can't take stuff like that for granted.

Jack Riedy (Photo: Haley Gallinadelapena)

Is your new song “My Friends Were Right” a standalone single or a preview of your second album?

I am working on a second album. We've got a few other songs that are close to being finished, and then I'm writing some new songs, you know, building towards a second album, but I’ve still got to figure out what the title is going to be and kind of cohere the concept for it, whatever that might be. But I'm really excited about the first couple songs that we've put together. And yeah, “My Friends Were Right,” I definitely wanted to get out this year before the summer, because I think it's a very fun song you should listen to outdoors.

I definitely think of it as kind of the start of whatever album two will be, but it's still a little ways away. So I'm really excited to kind of have this one out and about, and we're going to have a video ready for it within the next few weeks as well, that I'm really excited to get out there. So yeah, really excited about it.

You wrote the chorus of the song back in high school. What was it like revisiting your old songwriting?

I mean, it was a trip. To be frank, it's definitely a relief that the riff to it is sticky enough that I could kind of stick with it this distance later. The hardest part as far as finishing the song was sort of just tweaking the perspective. I think the narrator (has) a very teenage perspective, but there was still a little too much woe is me in the lyrics that I had first written as an actual teenager. That was definitely kind of a balancing act. How do I convey this with a little bit more adult perspective to the lyrics?

They talk about the sense of smell. It's really good for your memory. But so is music, especially something that I had first worked on and recorded. I mean, there's recordings of this song that I did in like 2012 or 2013. My voice is higher and I'm playing the guitar differently. The instrumentation on it is a little different. It's a real trip to go back that far. I'm really happy to have it in a finished state and out there for everyone else to hear it. 

Any chance of those archive versions being bonus tracks?

Yeah, we'll see. I mean, they're not bad, right? I was definitely a little nervous to go back to something that old creatively. But yeah, we'll see. I don't know if it's something I'm ready to share with everybody else just yet. We'll see about that. I’ve got to figure out who exactly played on it back in the day. I know some of my friends from high school, but I'd have to double-check some of the parts. Not sure who put them down. So we'll see. No promises.

Jack Riedy and the Dealbreakers appear at Reggies(2105 S State St.) on Wednesday, July 1 at 7pm. Tickets (starting at $12) are on sale now. 21+

Anthony Cusumano

Anthony Cusumano is a comedy writer, performer, and producer based in Chicago. In 2023, he launched The DnA Sketch Show, a recurring variety show, and in 2024 he wrote and directed the critically acclaimed musical Miracle at Century High School.