Tanner Dane v. Chicago Parks & Rec
- Julie Simmons
- 4 hours ago
- 5 min read
By Julie Simmons | Music Journalist
“I don’t want to implicate myself because that’s an ongoing legal battle. We have so many lawyers right now volunteering their services to come out and interpret the law of public assembly. They’re basically cheerleading us on and telling us to keep doing it.”
At The Wormhole Coffee in Chicago's Wicker Park neighborhood, singer, songwriter, and guitarist Tanner Dane is describing the ongoing standoff between his R&B band Hollyy and the Chicago Park District.
What started as a last‑resort busking initiative has turned into a bi-weekly ritual where hundreds - now a couple thousand - of picnic‑blanket‑toting residents flock to the AIDS Garden on Belmont. A mini‑Ravinia by accident, the city is now calling the police and pressuring Dane to shut it all down.
Our story begins with an all‑too‑common plot point: when perceived failure meets desperation entwined with destiny.
Dane summarizes, “Last year, I had a summer tour lined up [Tanner Dane solo project] that fell off last minute. I came home from L.A. and was like, ‘What do I do?’ I was so behind on scheduling shows. I spoke with one of my managers and he was like, ‘I would start busking, to be honest with you.’ So later, I was chatting with the Hollyy boys and said, ‘Hey, I think I’m just going to head to the lake tomorrow. Whoever wants to come, let’s do it. Let’s just have fun.’”
Their first location, at Montrose Beach, was challenging. People showed up, but rather cinematically, Dane’s microphone failed, forcing him to vocally compete with the horns and amplified guitars and keys.
The instruments won. But he left convinced that with working gear and a better location, they could pull it off.
He was right.
Belmont Ave provided concrete steps, a perfect view, and even a dog park. Hollyy’s sunset pop‑ups ran from August 2025 until winter shut them down, returning in May 2026 bigger than ever.
May 26, 2026
A member of Reddit’s sub‑forum “AskChicago” posts:
“Why are there literally hundreds of people at Belmont Harbor/the AIDS Garden right now?
I went on a walk at the lakefront this evening and was surprised to encounter a gigantic swarm of people leaving the park—literally hundreds of people, no exaggeration. The police had the Belmont Harbor parking lot blocked and there was another cop car sitting in the middle of the AIDS Garden. Was there an event there today? I tried googling it but couldn't find anything. It was way too many people to just be people enjoying the weather.”
Comments:
“hollyy concert”
Back at Wormhole, Dane flips a tendril of blonde hair from his eye. “We’ve found that young people love a good community‑based TikTok trend. At the same time, there’s all walks of life at these shows. Older people love R&B. And then there’s the dogs. It just keeps growing.”
Once a crowd reaches Hollyy’s scale, the city expects porta‑potties, parking, zoning, tents, and possibly lifeguards. Dane’s been told the cost is around $20,000.
As Chicagoans in the music scene know, there are several pop‑ups around the city from the Wiener Circle’s parking lot to Redline Chicago’s EDM raves in abandoned warehouses to the “Secret River,” a floating concert series which (since 2022) took place on a concrete island under the Belmont Avenue Bridge along the North Branch of the Chicago River. But rather than shut that down, the city’s Department of Cultural Affairs and Special Events granted its founder, Ben Kinsinger, $5,000 to host a musical parade last summer. This year, the Secret River has relocated to The Wild Mile boardwalk.
As the system’s intended to do, anything can be made legal with enough money but that’s not the point. While Hollyy currently relies on ticket sales and merch to earn money, they’re passionate about keeping the lakeside shows free. While maintaining their DIY ethics, there’s an unspoken hope that by giving thousands of people free performances, karma will eventually allow them to become professional, well-paid touring musicians. Until that time, Parks and Rec continues to call the police and issue cease‑and‑desist warnings.
Dane shares proudly, “[The park district] was so surprised each member of our band has their own busking permit. But a busking permit doesn’t get you out of ‘you shouldn’t be amplifying your noise’ or ‘you shouldn’t be blocking public gathering way,’ which, arguably, we’re not.”
Dane confesses reluctantly, “We’ve been told we’re lucky our music is mellow.”
It is.
Since 2020, Hollyy has been delivering nostalgic R&B originals with luscious horns, keys, guitars, and unmistakably passionate vocals. After years of releasing singles, their first LP, The Weight of This Heart, was released in 2025.
As it turns out, what’s good for Hollyy is good for his solo project.
Dane updates, “The label I’m on reached out to me and basically said, ‘This is exactly what we asked you to do. Let’s get back in talks.’”
Dane’s first solo LP, Pull Tabs, was also released in 2025. Monthly listener numbers are expected to jump this summer when he opens for the Irish folk trio Kingfishr at their Lollapalooza Aftershow at Lincoln Hall on July 30. Tickets allegedly sold out within two minutes.
Ninety minutes passed. The clot of remote‑working customers at The Wormhole is thinning out as lunchtime approaches. As I study the playful ’80s memorabilia on the walls in the distance, I’m reminded that the present is always cloaked in the past.
Cupping my hand around the lid of my to‑go cup, I ask, “Why do you think Chicagoans are showing up?”
Searching the ceiling, he answers, “People are coming because they appreciate DIY and the music, the water in the background, and the sunset. All those elements make a core memory. Last year, people DM’d us and commented that our shows [last year] were the best part of their summer.”
Nodding a little, he summarizes, “In this apocalyptic, political world we live in, things are villainized every day. The Hollyy / Tanner Dane sunset shows are a reminder that our city is a beautiful place and there’s a beautiful lake and there are really cool things that happen, and we don’t need to travel to see them. We just need to walk 10 minutes in our own neighborhood.”
For the next Hollyy / Tanner Dane Tuesday sunset show at Belmont Rocks, please check out Hollyy.band and Tannerdanemusic on social media.
***
Do you like to talk about music in a way that's intellectual, civil and collaborative? Ask to join the Facebook Group, Music Makes You Think.