New Eyes on Familiar Streets: Todd Gross in New York City

Photographing on the streets of New York City is hardly a novel venture. Artists like Bruce Gilden and Elliott Erwitt made careers out of wandering the avenues, chronicling people navigating the metropolis. The beauty of the Big Apple — and its appeal for street photographers — is that it’s always changing, and the change is utterly electric.

These streets are Todd Gross’ playground, and his pictures illustrate the humor and darkness that coexist on every block. One moment he’s capturing the comedic intersection of two young girls, a 30-something-year-old man and a sign reading “Get Old” (slide # 7) and the next, he finds an old man resting in the shadows as a black bird seemingly waits for his end (slide # 8). In a city that most of us feel we know pretty well, Gross’ work stands out as unique, funny and sometimes profoundly sad, all at once.

But he has never worked as a professional photographer.

A native of Queens, Gross followed a different path with his photography. Now 43 years old, he loved MAD magazine as a kid and drew his own versions of its comics in grade school. “Then I met friends who could draw better than I could, and I was like, ‘Oh, my drawing kinda sucks,'” he says. After attempting other creative outlets, he found photography in the mid-1990s. He started out shooting black and white film, and as early as 1998 was working with a kind of proto-digital camera that stored photos on a floppy disk.

A high school dropout, Gross has worked a wide variety of jobs, from coding emails for a credit card company to coordinating camera crews for ABC. While working at a web company in the early 2000s he discovered blogs. In March 2001, he started to blog under the alias Quarlo, named after a cop from the surreal, sci-fi TV series The Outer Limits, and posted only photos, which was somewhat rare at the time. The relative success of this venture inspired him to learn about the street photographers who came before him, and to start shooting color film.

He learned about Gilden, Martin Parr and Cartier-Bresson. He also noticed the work of Boogie and Cary Conover on the letters page of Time Out New York. This was the first time, after years of shooting, that Gross encountered any photographers who could be called legitimate influences on his own work.

Noting that many viewers characterize his work as crazy or zany, Gross acknowledges that “a lot of it is funny,” but he never set out to consciously shoot that way. “I want [my pictures] to be darker, more mysterious, more brooding, because that’s part of my personality, too.”

Gross kept shooting and blogging until 2005, when a storm of bad luck took his focus away from his work. He went through a bad breakup and started working on more non-photography-related projects and day jobs than he had in the past, which necessarily limited the time he spent photographing the streets. In fact, he more or less stopped shooting entirely during this time.

Things didn’t turn around until 2010, when he bought an iPhone. Once again he was carrying a camera all the time. “It totally brought back my enthusiasm — but not really enthusiasm for the phone itself. The device was just the spark,” he says. After a month or so of working with the iPhone he broke out the old film camera, then eventually moved over to a DSLR.

After all he went through before coming back around to street photography, Gross says he’s noticed an improvement in the quality of his work. “This is what I do, and I probably had to go through [the bad times I’ve had] in order to realize that.”

As for never working as a professional photographer, Gross is looking to change that — although he admits to some ignorance about the ins and outs of the industry.

“I’m like a space alien, sometimes,” he says. “I don’t know how that world works.”

Todd Gross is a New York-based street photographer. To see more of his work visit quarlo.tumblr.com.

Tanner Curtis is an associate photo editor at TIME.com.