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"What's that for?" a female officer is heard asking.

"I was going to write my name," Gallagher responded.

"So, you were going to write your name on the pavement?"

"Yes."

"Like graffiti?" she urged.

"No, no—I sign my pieces."

The officers arrested him for making graffiti. When Gallagher protested, saying that he didn't understand why he was being taken in, one of the cops told him: "We'll make you understand when we get to the precinct."

The charges were eventually dropped, but not before he spent 17 hours in jail with men who had been caught smoking cigarettes in the subway and jumping the turnstile. When he told them he was there for sidewalk chalk art, "people thought it was a complete joke," he says. But Gallagher sees no humor in it.

Last week, Gallagher filed a notice of claim, notifying the city of his intent to sue for false arrest, unlawful imprisonment, and pain and suffering. He is seeking $5 million in damages.

Over the years, Gallagher has had his share of run-ins with cops—he used to be a true graffiti artist and was arrested multiple times for tagging. However, after a fellow graffiti artist and friend was struck by a train and killed, Gallagher put away the spray paint forever. Now he shows paintings at Bushwick's Ad Hoc Art Gallery and is working on two books inspired by graffiti and his chalk shadow outlines. But the majority of his work is still on the street—now in a water-soluble medium that, his lawyer asserts, is perfectly legal.

Gallagher says his $5 million complaint is not about the money—he knows it's unlikely that he'll be able to squeeze much out of the city—but about the principle. "I want peace of mind—no fear of arrest or harassment, freedom of expression, knowing that I can go to sleep at night doing what I do without fear of being incarcerated," he says. "I think [the NYPD] should reassess their priorities and not waste taxpayer dollars on policing people for chalking sidewalks." Which is apparently something they've been doing quite a bit of over the years.

Hani Shihada, another of the city's sidewalk artists, says he's suffered police harassment for years. Shihada, best known for his sidewalk replicas of Sistine Chapel scenes, says he has been taken to court more than 20 times, and each time the charges were dismissed. "I bring pictures of my work and show the judges, and the judges smile," he says.

Even children aren't immune from the chalk police. Last year, the Sanitation Department demanded that six-year-old Natalie Shae remove her "graffiti"—sidewalk chalk doodles on her own stoop—and made international headlines.

Meanwhile, the harassment against Gallagher went on. Soon after his night in jail, he was in Boreum Hill outlining the shadow of a light post in front of a bar. As several customers watched him work, the cops arrived to put the kibosh on his chalk-handling once more. The confrontation eventually drew four police cars and ended only when Gallagher agreed to wash away his drawing.

Paul Hale, Gallagher's attorney, says the city's interpretation of what constitutes graffiti is skewed. Under state law, graffiti is defined as the "etching, painting, covering, drawing upon or otherwise placing of a mark upon public or private property with intent to damage such property." Chalk, Hale points out, doesn't damage anything.

At least one New York judge has made the distinction between true graffiti and sidewalk chalk. Just one day before Gallagher was arrested, a federal judge found a Syracuse man not guilty of vandalism after he was arrested for writing messages in chalk to Hillary Clinton in front of a federal building there. Chalk, the judge opined, doesn't damage property and therefore can't be considered graffiti under state law.

New York City, however, has its own defacement ordinance that could still get some chalkers in trouble for simply leaving a mark on sidewalks or buildings. Echoing the words of graffiti artist Ramo from New York's classic hip-hop flick Beat Street, Gallagher says: "If art is a crime, may God forgive me."