On one of our August 2020 podcast episodes, we asked rising singer songwriter GAYLE what the perfect place was to listen to her single, “Orange Peel.” She told us “Summer time. Sunset. Driving down a long winding road.”
On November 29, Brighton Music Hall in Boston was a close second.

The audience joined the Nashville-based artist on her first ever tour as an opener for Winnetka Bowling League, and for her debut Boston show.
With just her and her guitar, she kicked her set off with “z” and “Horny,” teasing “One day I’ll find out how to be appropriate. Today is not the day.”


Things came full circle for GAYLE when she performed her song “Dumbass,” explaining that she wrote the single as an insecure 13 year old about being 17. Now 17, the song has taken on new meaning. “I looked in the mirror and was like who the f*ck am I trying to please because it’s not myself,” she shared.
Along with her own discography, she included an ode to the woman of rock that have come before her. “They had a shit ton more criticism than we do now, but it still needs a lot of change,” she told the crowd. “I appreciate that things have changed for the better and continue to do so.”
As part of her homage, she performed a haunting rendition of Alanis Morrissette’s “You Oughta Know,” complete with vocal runs, acapella verses, and a slowed-down melody.

During each song, there notably wasn’t any side conversation. All eyes were on GAYLE, clearly mesmerized by her tongue-in-cheek lyrics and powerhouse vocals.
Throughout her set, GAYLE took moments to joke with the crowd and share her food escapades around Boston, specifically a visit to Mike’s Pastry, “I had my first cannoli yesterday. It was magical. Better than sex.”
The crowd went wild when they recognized the final song in GAYLE’s set, her viral single “abcedefu.” She sang the angier version because, “I’m going to f*cking say f*ck as much as I can,” she said.




“F*ck you and your mom and your sister and your job and your broke ass car and that shit you call art,” the crowd sang back, especially loud during an acapella call and response to close out the song.
To cheers, she ran off the stage, but not without returning to pack up all her own equipment.

Check out GAYLE on tour with Winnetka Bowling League. Grab tickets here!
Listen to our podcast interview with GAYLE below!
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Amelia Cordischi, Founder and Editor-in-Chief of Juice Box Press, is an accomplished digital marketing professional with over a decade of experience in media and communications. Her work has been featured in notable publications, including The Boston Globe. A communications graduate of Simmons University in Boston, Amelia served as manager of Simmons College Radio (“The Shark”), where she also launched and co-hosted her radio show, The Find.
In addition to her editorial work, Amelia is an established freelance photographer, with bylines in Blended Magazine and CelebMix, capturing artists and cultural moments across the music and media landscape. Her career began at WCVB-TV’s Chronicle, the ABC affiliate in Boston, where she gained firsthand experience in broadcast journalism and storytelling.
When she’s not taking photos from the photo pit, interviewing emerging artists, or crafting the next Juice Box Press feature, Amelia can be found thrifting and exploring the world of sustainable fashion.