Tanner Dane hops in the car while parked in Wicker Park to talk about turning a canceled summer tour into one of the most exciting grassroots live music movements in Chicago.

After his initial plans fell through, Tanner took matters into his own hands, launching spontaneous, pop-up Tuesday night acoustic performances along the Chicago lakefront, eventually settling in near the AIDS Garden. What began as an effort to get back to the basics exploded across TikTok, drawing massive crowds, the attention of Chicago Park District officials, and even an encounter with the police that ended with a citation, a complimentary officer, and pro-bono lawyers stepping in to help.

In this episode, we cover:

• Building community through lakefront pop-ups and leveraging TikTok to connect directly with fans.
• Transitioning from his band Hollyy into a deeply personal solo project.
• Collaborating with Chicago rock veterans Scott Lucas (Local H), Blake Smith (Fig Dish, Caviar), and drummer Jason Batchko.
• The inspiration behind the post-breakup single “Hardest Lessons Learned”.
• Growing up on Stax, Motown, and classic soul records.
• Securing a major label record deal and gearing up for his first ticketed, headline hometown show at Schubas on November 5.

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