“We’re really gonna try to muss up City Winery,” laughs Adrian Blake Enscoe, one-third of Brooklyn indie-folk-pop-Americana outfit Bandits on the Run, before Sydney Shepherd (his partner in life and music) proclaims, “We’ve performed everywhere from Broadway to the subway.” That is actually true… Adrian, Sydney, and Regina Strayhorn came together just over a decade ago while busking NYC subways, had a breakout hit when 2019’s “Love in the Underground” (a song that I find out during our recent chat was about Adrian and Sydney’s meeting) was featured on NPR Tiny Desk Contest’s Top Shelf, and Adrian actually performs on Broadway as Little Brother in Swept Away, The Avett Brothers’ musical… And the band have done quite a bit in the gaps, as well, becoming known for their combining of cello, guitar, and accordion (along with found-percussion) with three-part harmonies and rotating lead vocals.
I’m chatting with Adrian, Sydney, and Regina via Zoom, ahead of their July 20th headlining show at The Loft at City Winery, a far cry from their last area appearance, which took place last January at Kung Fu Necktie (a photo from that show actually serves as the cover image for February single “Let’s Go Below”), which I regularly find myself describing as resembling, “a brothel in a Rob Zombie movie.” Although, all joking aside, the band does say that there are certainly some fun aspects to playing listening rooms like City Winery. “That’s where I feel like people will contribute the most, more so than when they’re at a festival or in a bar. You have a more engaged audience when they’re seated,” Adrian says, while Regina adds, “When we play somewhere like that, it can be fun to see how much of our busker aesthetic we can bring.”
Bandits on the Run’s summer tour comes behind the May release of The Shakespeare Tapes, the group’s first EP since 2021’s Now Is The Time, which dropped shortly after I first met the trio that summer. The Shakespeare Tapes began as a collaboration with director Peter Anderson, who hired the band to create a soundtrack for his production of As You Like It at Carnegie Mellon University. The show eschewed a traditional binaried lens and had Sydney and Adrian instead writing for the roles whose voices they best fit, with Shepherd voicing the role Orlando and Enscoe voicing that of Roaslind. The sonic aesthetic of Anderson and Bandits on the Run’s As You Like It would go on to be lovingly referred to by the band as “Shakespeare Americana.”
However, this wasn’t the first time Bandits on the Run put their music to use theatrically. The trio has composed music for Netflix animated series Storybots, in addition to Peter Hedges-penned feature film The Same Storm (2021), which actually led to one of Bandits’ current projects, a musical adaptation of What’s Eating Gilbert Grape, for which Hedges wrote both the original novel and screenplay. I admit that I was unaware that the Academy Award nominated film – featuring Johnny Depp, Leonardo DiCaprio, and Juliette Lewis – was originally a book prior to reading the group’s latest press release. “The novel is great and worth the read, although very firmly placed in the ‘80s and ‘90s,” jokes Adrian. And while the band tells me that that particular musical is pretty far along in the development stages, they tell me that there’s another musical that they’re just getting started on…
They also all admit that writing for a musical or film or series isn’t necessarily as different from making music for an album as one might expect. “I kinda feel like with all of the songwriting there’s an element of play and being inspired by what’s in front of you at the moment… What is different is the source of inspiration,” Regina tells me, before Sydney goes on to explain that it’s really more the production that most differs from that of a band or singer/songwriter. She also tells me that, in recent years, the group has gotten more confident in blending their love of theater and more traditional live music: “We’ve gotten a bit bolder infusing more of our theatrical work into our music.”
The band[its] have spent a decent chunk of 2025 playing live, opening nine dates for The Wood Brothers this February (“They were just so lovely, nice guys, and consummate artists. And we got to pop up and sing with them a couple of times. That’s the kind of support we’d like to be able to do for someone else in the future,” says Sydney.), playing a residency at NYC’s Bowery Electric, and performing June sets at Westport, Connecticut’s Levitt Pavilion and Milwaukee’s Summerfest 2025, where Adrian joined The Avett Brothers for an encore performance of “Swept Away.” And Bandits on the Run tell me that they’re thrilled to be able to spend much of this summer on the road. “In a time like this, people are looking for joy and connection,” Sydney explains, before Regina adds, “With everything going on right now, people are looking for moments of things that have been consistently enjoyable, good vibes and community vibes and being more vocal about gratitude toward each other.”
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