Hopalong Andrew Is the Hardest-Working Cowboy Musician in Brooklyn

Traveling the children’s-entertainment circuit with the lasso-swinging performer.

Andrew Vladeck keeps four weather apps on his phone and checks them at intervals throughout the day. In temperatures higher than 36 degrees, he can still strum his guitar, but much colder and his fingers freeze. “Suddenly drizzling!” he once texted me as I was en route to a show. “The weather app said no rain and now it’s raining and there are two people here.” But a recent Tuesday was ideal: sunny, mid-60s, the trees in bloom. About 50 caregivers and children gathered in Underwood Park, in Clinton Hill, to enjoy Vladeck’s set. Preschoolers mobbed the stage — pogoing, shimmying, and singing along; one skidded into and nearly toppled Vladeck’s cymbal stand — while some of the tiniest kids, mere babies, sat on laps and cried. “Who can clap?” he asked after a couple of verses of a song called “Can’t You Dance the Polka?” “Who can hop?” Then he praised the children in his silky twang: “Good, good.”

The performance ended promptly at 12:45 p.m. It was nap time for many in the audience but already the second gig of the day for Vladeck, better known as Hopalong Andrew, the ersatz cowboy and one-man band. No region of the country, perhaps, is more saturated with indie kids’ performers — they call themselves family musicians — than brownstone Brooklyn, where there’s a troubadour for every musical taste. Elena Moon Park, who plays the violin, trumpet, mandolin, jarana, spoons, and musical saw, focuses on Asian folk and traditional music. Michael Hearst composes albums with themes such as ice-cream trucks and unusual animals — the blue-footed booby, the sea pig, and the like. Suzi Shelton is locally famous for her song “Go, Firetruck, Go.” As working artists, these performers draw audiences however they can, by playing in schools and libraries, hosting classes in storefronts, or working birthday parties.

By reputation, Hopalong Andrew outhustles his competition. He lives in Clinton Hill and posts nearly a dozen gigs a week on Instagram — mostly in Brooklyn parks, but also at the Whole Foods in Gowanus and Tribeca and at the City Point mall. He plays 400 to 500 shows a year and bikes to and from each one, towing his kit in a secondhand trailer: guitar, harmonica and neck holder, seafoam-green Samsonite suitcase (doubling as both stool and drum), drum pedal, boot bells, cymbals, lasso, a stack of child-size hats, and three collapsible baskets for holding, respectively, tambourines and shakers, chiffon scarves, and a laminated QR code for Venmo payments. Some weekends, he will do four birthday parties in addition to his public schedule. He remembers performing chez Jason Sudeikis and Olivia Wilde back in the day and believes the optimistic mind-sets of Hopalong Andrew and Ted Lasso are aligned. For two years, before the pandemic, Adam Neumann of WeWork and his wife, Rebekah, hired him to play at their house for their children two times a week.

Vladeck, who is 52, grew up mostly in the suburbs of New York City and as a teenager had a singular ambition: to become a singer-songwriter with American folk roots like his idol, Bob Dylan. At Columbia University, he formed his own eponymous band. Aaron Dessner auditioned once and Vladeck turned him down: “He was literally bursting with musical ideas. It was going to be too limiting for him.” (Dessner went on to co-found the National.) Through his 20s, Vladeck persevered with modest success playing small venues like the Mercury Lounge and Sin-é, always while working a day job. Then, after 9/11 and while living in Chinatown, he and his friends formed a folk ukulele trio called the Honey Brothers, mostly to cheer themselves up. One evening, Adrian Grenier came to hear them at the Living Room. At the time, Grenier was considering a career as a music producer. “He was like, ‘Oh, I want to be in this band! Please!’ So we were like, ‘All right. If you really want to,’” Vladeck recalls. (Grenier doesn’t remember asking to join, but he did offer to help modernize the band’s sound.) Eventually, he came on as the drummer.

When Entourage aired on HBO in 2004, the Honey Brothers had a megamoment. The whole world wanted a piece of Grenier. “Everyone suddenly became Americana-folk fans,” Grenier says, laughing. He remembers playing Mansion, a nightclub in Miami, with “Biggie bumping on the speakers and the curtains open and the voice says, ‘Ladies and gentlemen, the Honey Brothers!’” The band tried to play as fast as it could before mutiny erupted over the switch from club music to ukulele. Vladeck remembers once sharing a bill with Gloria Estefan and Queen Latifah and doing photo ops with Kim Kardashian. But by 2012, the Honey Brothers had dissolved and Vladeck’s solo career plateaued. He was in his 40s, still working odd jobs, still waiting for his big break. Vladeck asked a friend at a record label for advice: “How come I can’t get to that next level?”

“Vlad,” the friend said, “did you ever think you’ve gone as far as a quirky banjo player can?” Vladeck had to concede that maybe his friend had a point. He does not have the exhibitionistic instincts of a front man, and he is not “a masterful musician or sideman,” he told me. “I don’t know what to say. My playing is decent.” (During the Honey Brothers’ heyday, the band paid for lessons so Vladeck could sharpen his skills on lead guitar.) He continued working on his solo career, but “I was Sisyphus rolling the boulder up the hill,” he says.

Hopalong Andrew came to him by chance in the summer of 2012, whena friend asked him to fill in for his family-music gigs. Vladeck saw the persona in a flash. He was already a collector of vintage cowboy shirts. In addition, “I know every folk song, and I play all these instruments, and I love cowboy music.”

Vladeck’s Instagram is filled with photos and videos from grateful parents. He’s had children dress as him for Halloween in a fringed jacket and boots. But he knows his continued success doesn’t depend on these parents or even on their kids, whose devotion, though intense, is fleeting. By the time they’re 5, the children enter school, and their nannies frequently move on to families with younger children. Vladeck, who has no children of his own, is indebted to these nannies for bringing a new generation into his circle every season. At Underwood Park, Sandy Tommy was there with her 13-month-old charge. She has been following Vladeck for more than seven years, over three subsequent families.

Over time, the nannies have grown protective of Vladeck and, in particular, watchful for interlopers who would enjoy his shows without paying the $20 drop-in fee. (Already, Hopalong Andrew charges less than most of the competition.) In the parks, a number of the nannies have sometimes taken it upon themselves to solicit fees from the evaders — “A good initiative,” says Shakiera Roseman, who works as a DJ and takes side gigs as a nanny. The scofflaws are mostly parents, she tells me. (“Maybe they say they’re going to Cash App him and then they forget. I don’t know,” she says.) Last spring, some of the Caribbean-born nannies asked Vladeck why he never played soca music. He rose to the challenge, learning “Famalay,” by Skinny Fabulous, Machel Montano, and Bunji Garlin, and “Mind My Business,” by Patrice Roberts. Roseman took a video of Vladeck playing and sent it to Roberts, a superstar in Trinidad and Tobago. Roberts reposted it, creating a viral hit. Vladeck even made an appearance on a Trinidadian news channel. Now he’s making an album called Everybody’s Invited to the Party: The Multicultural Cowpoke (a working title), a celebration of the history of the West. Hopalong Andrew has liberated him, he says. “I can perform every day, and I don’t have to be out late if I don’t want to be,” he told me. “It’s like my Andrew Vladeck musical self is jealous of my Hopalong Andrew self.”

This article appeared in the May 22, 2023, issue of New York Magazine

Photo Credits:

photos courtesy of Peter Fisher