Portland’s Hottest Cocktail Bar Isn’t a Bar At All

How Jimmy Drink World founders Hayley and Zach Wilson launched pop-punk pop-ups that connect Portland’s hospitality industry to its music scene.

Before the doors even open, there is a crowd forming outside. A sea of pop-punk fans donning Blink 182, Paramore, and fittingly, Jimmy Eats World T-shirts wait patiently. Inside, Hayley and Zack Wilson, the founders of Jimmy Drinks World, complete last-minute tasks and touches. When four o’clock rolls around, it’s time to let everyone in. Immediately the bar runs 15 people deep, each ordering two or three drinks at a time. Bartenders from Portland and Boston are posted up, shaking cocktails as quickly as humanly possible. From the first song on the playlist, everyone is singing along inside the hottest new bar in the city.

Since Jimmy Drinks World’s arrival in July 2021, it has been one of Portland’s most sought-after pop-ups. Founding couple Hayley and Zack Wilson conceived of it during late nights after Hayley finished her shifts behind the bar at Portland Hunt and Alpine Club and during last call while they were out seeing shows. Originally conceived as a brick-and-mortar space, in the depths of the pandemic, when restaurants and bars were closed, the idea turned into a pop-up with the vision of connecting the hospitality industry and the music scene.

Both Hayley and Zack have deep roots in music and hospitality. Before arriving in Maine, they spent their early 20s in Boston seeing shows as often as possible. Zack ran sound and played in bands, and Hayley started her career behind the bar. Since moving to Maine, Hayley’s bartending career has taken off; in 2021, she was named a “Bartender in Residence” at Punch magazine, which highlights up-and-coming industry professionals over the course of the year.

Hayley says the majority of her friends who play in bands have worked front- or back-of-house at some point in their lives. “What we personally run into frequently is that we miss out on shows where we could be supporting local spaces due to the schedule conflict of having to work busy weekend shifts,” she says. Doing late-night pop-up events on Sundays and Mondays allows Jimmy Drinks World to grow a community of like-minded folks who love music and love cocktails.

But Jimmy Drinks World goes beyond just connecting pop-punk lovers. Giving back was always part of Hayley and Zack’s plan and a priority from the start. Supporting small, independent music venues when they had no source of income during COVID not only helped the venues but also reminded everyone attending how important places like these are in a community. Hayley told me, “When COVID hit, the music industry took a massive blow. We watched as some of the most important venues to us closed across the country and feared for the small venues, like Sun Tiki in Portland, and what their futures would look like.”

Each pop-up is held at a different bar around Portland (and sometimes Boston) to keep the scenery changing as well as to bring folks into new places where they might not expect to encounter a loud pop-punk playlist. They also work with multiple food trucks and small food vendors so the menu is ever-rotating. “We do our best to cater to each hosting space and to create a vibe that fits in its walls while still being Jimmy,” says Zack. In just one year, Jimmy Drinks World has done exactly that: from “Acoustic Jimmy’s” to pop-punk karaoke, each experience is unique.

Cherry Lemonade performs at a Jimmy Drinks World event at Portland Hunt + Alpine Club.

At the one-year anniversary of Jimmy Drinks World in July, tables were pushed aside so the traveling dragshow, Curbside Queens, could take turns performing. Baskets provided by local venues and restaurants were raffled off to raise money for the event’s chosen charity, Indigenous Women Rising. It had all the energy of a great show in a great venue where everyone knows the songs by heart. The evening ended with Jimmy Drinks World founders, Hayley and Zack, standing on top of the bar, thanking the crowd, and then shot-gunning beers before saying goodnight.

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