Stand for ten minutes on any corner of Flatbush Avenue and you’ll see a stream of dollar vans with Haitian flags tied to their antennae, Bible scriptures in colorful decals across their windshields, advertisements for local reggae concerts pasted on their side windows, and forests of rainbow-colored air fresheners dangling from their rearview mirrors. The vans are a big part of life in Brooklyn, especially among people with Caribbean roots; they’ve even inspired reggae tributes and a series of in-van concerts by local hip-hop artists called Dollar Van Demos. A twenty-four-year-old unlicensed van driver who goes by the name Skates operates one of the most recognizable vehicles on Flatbush, outfitted with a massive sound system that can project inside and outside the van, plus fifteen synchronized television screens that broadcast a steady stream of rap and hip-hop music videos.

During the 2013 fiscal year, the Taxi and Limousine Commission impounded more than six hundred illegal vans, two hundred and forty of them in Brooklyn. Still, unlicensed dollar-van drivers like Skates remain ubiquitous in the borough and are in a constant legal tug-of-war with city authorities, dodging fines and repossession as they navigate the streets. “You hear about the vans by word of mouth,” Patrice Gibson, a thirty-year-old teaching fellow at Long Island University, said. “A friend told me, ‘Why are you taking the subway for two fifty when you can take the two-dollar van?’ But also, I’m Guyanese, and we have vans like this back in Guyana, so when I saw the van on the street I knew what it was.”

On several Brooklyn side streets you can still find locals using little sedans to run illegal “dollar cabs.” When the T.L.C. and New York City Police Department come around, illegal vans and cabs warn each other over C.B. radio. They park for the day, and sidewalks overflow with people waiting for the bus instead.

In the eighties and nineties, dollar-van drivers—mainly black, mainly immigrants—had a difficult relationship with the N.Y.P.D. Leroy Morrison, who has been driving vans in Brooklyn for more than twenty years, recalls, “Back in the day, officers used to harass us day and night: throw van keys on the roof, throw them in the garbage, bring us into the station just for driving a van.” An N.Y.P.D. spokeswoman didn’t respond to a request for comment on Morrison’s recollection.

These days, many dollar-van drivers in Brooklyn—legal and illegal alike—enjoy a relatively good rapport with the police, especially compared to past relations. Skates, for example, waves and calls out to several officers along his route. Still, many drivers complain that the N.Y.P.D. issues too many tickets to both licensed and unlicensed vans. Winston Williams, a licensed van driver and the founder of Blackstreet Van Lines, recalled an incident from 2009: “One cop was sitting out and issuing tickets to van drivers for failure to signal for violations that we weren’t committing. In two days, he issued tickets to more than six van drivers. I got the van drivers together, and we appealed to the Civilian Complaint Review Board.” Winston fought his ticket in traffic court and was eventually found not guilty. “But I can’t be going to court to fight these every week,” he said. In Brooklyn, police and the T.L.C. conduct frequent dollar-van sweeps, during which they issue tickets for moving violations and seize unlicensed or under-insured vans. Brian Laffey, a community-affairs officer with the Seventy-Eighth Precinct, explained, “It’s about safety, and I field a lot of community complaints about how these vans drive aggressively. We’re not trying to hurt the honest guys making a living, but if you do something illegal, if you’re picking up a hail or picking up on a bus stop, I don’t care if you’re accredited with signage on the side of your van—you’re gonna get a ticket.”