Northbrook native Jordy is bringing ‘cool boy summer’ to Northalsted Market Days

Jordy has a confession to make.

“Honestly, this will be my first Market Days,” he said ahead of the long-running Northalsted/Lake View street festival, which he headlines on Sunday.

Although the 31-year-old GLAAD and Queerties-nominated singer/songwriter, born Jordan Shulman, grew up in Northbrook, he “never really lived in Chicago as an adult.” He left for college, majoring in English at Boston University, followed by a move to Los Angeles in 2017 to pursue his dreams of becoming a bona fide pop artist.

JORDY sits at Senior Citizens Memorial Park in Bucktown, Thursday, August. 6, 2026.

“Early in my career, I kept hearing this word ‘pigeonhole,’ like, ‘don’t pigeonhole yourself as the gay artist,’ but that thought hasn’t crossed my mind once,” Jordy said. “At the end of the day, I’m an openly gay man who is very upfront about that in my music.”

Pat Nabong/Sun-Times

Jordy

When: 9 p.m., Aug 9
Where: Northalsted Market Days, Halsted Street from Belmont Avenue to Addison Street
Tickets: $20 suggested donation
Info: northalsted.com

That goal was met in 2019 with his breakout hit “Just Friends” and reached a fever pitch in 2023 with “Story of a Boy,” where Shulman reinterprets the lyrics of rock band Nine Days’ Y2K hit “Absolutely (Story of a Girl)” through a queer lens. The song quickly went viral after it was featured in social media posts where transgender people shared before-and-after photos of their transition. His popularity led to appearances on “The Today Show,” “The Kelly Clarkson Show” and “Good Morning America” and garnered 350 million streams of his catalog to date.

The success of “Story of a Boy” and what it has meant to the LGBTQ community has been the lead-up to the singer’s appearance at Market Days (and Chicago Pride Festival in 2023), and he couldn’t be happier about how his career has played out.

“Early in my career, I kept hearing this word ‘pigeonhole,’ like, ‘don’t pigeonhole yourself as the gay artist,’ but that thought hasn’t crossed my mind once,” he said. “At the end of the day, I’m an openly gay man who is very upfront about that in my music. And pride is something that adds an extra layer of importance in what I do. It’s special to be in a space like Market Days where we’ve all kind of shared such similar journeys. Every single one of us at some point in life felt like we didn’t belong in a space and now we’re making up an entire space together, and I love that.”

That journey is a recurring theme on Shulman’s fourth album, “In Retrospect,” released July 10, that he defines as a coming-of-age-at-30 project. Across 11 tracks, he looks in the rearview mirror at how far he has come personally and professionally, from the Glenbrook North theater kid who spent hours alone in his bedroom listening to pop-rock queens Avril Lavigne, Hilary Duff and Michelle Branch, to now creating queer anthems himself and finding peace with it all, even the hard moments. “Some of my earlier songs [on 2021’s ‘Mind Games’ and 2023’s ‘Boy’] were coming from someone who just really desperately wanted a boyfriend or a man to validate him. Now I’m turning inward and finding all of that within me,” he adds.

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Jordy performs at Outloud Music Festival at WeHo Pride on June 7 in Hollywood, California.

Amy Waters

One of the most honest and heartfelt songs on his new album is the soft-spoken ballad “Normal People,” where Shulman comes to terms with being single and childless at an age he was sure he’d have his own version of the white picket fence. The song harkens back to a time he struggled with the idea of ever feeling “normal.”

“There’s a memory I’ll always have of the first year I came out, when I was 15,” Shulman said. His mom was dropping him off at the Highland Park Community House for a summer camp reunion, and as he started crying about what being gay meant for his future, she pulled the car over to offer words of encouragement.

“She said, ‘I promise you that you will be able to have a family. You will be able to have kids, I promise you that you’ll have this,’” he recalled. “I look back on that and I’m like, how lucky am I to have had a mother so loving and accepting of me? But it’s also like so many of us can relate. When we were that age, we saw ourselves having those dreams by now.”

Surprisingly, Shulman was met with some negativity around the track. “It hit kind of a bad corner of the internet, and there was a lot of homophobia in the comments … some of which said it should be a woman singing it,” he said. “I think people are sometimes shocked to see a man expressing an emotional response … and I think for myself it’s been part of subconsciously redefining what being a man means.”

That’s surfaced the past couple of months as the singer’s latest social push has been centered on his new pop-rock anthem “Cool Boy” and promoting #CoolBoySummer, where he wants to shift the meaning of the label. “I never felt like a cool boy growing up. And I still don’t really feel like a cool boy, to be honest,” he said.

As for what he hopes people will do in response to the hashtag: “Show me you. Show me your hobbies! Like I’m obsessed with reading and I want more boys to read. I want that to be a cool boy thing,” he said. “I want more people to talk about the s— they like and get excited about it. Embrace who you are and don’t let anyone dim your light.”

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