Jack Toolin is an interdisciplinary artist, working in traditional media, new media, performance art, and photography. His current photography projects are realized in either documentary photography or digitally manipulated forms, and he has been working on several AI projects that explore the problematics and limitations of AI.

His photographic practice centers on what he calls the "fringe economy" — an ongoing investigation into aspects of economic precarity, from empty retail spaces to the quest for compensation via tip jars. In his ongoing series Profit and Loss, Toolin steps outside of straight documentary, employing digital compositing, graphic embellishments, and text to indicate the stress of market-driven life, what he terms "psychoeconomics." Images from the project included in the exhibition Biennial Means Necessary, at PRZ Gallery, an independent gallery in New York City. Documentary photographs from the 3rd Ave. Corridor project were included in the independently published book, The B-Sides of Architecture.

Before concentrating on these projects, he was a founding member of C5, a groundbreaking new media collaborative whose work has been exhibited nationally and internationally, with a landmark appearance in the 2002 Whitney Biennial. His locative media project Perfect View (part of the C5 project The Landscape Initiative), is centered on the perception of the "sublime" in landscape, given our technologically augmented methods of apprehending place. It was exhibited at the San José Museum of Art, San Francisco Camerawork, Foxy Production in NYC, and as a solo exhibition at the Chelsea Museum, NYC. It is featured in Christiane Paul's seminal survey Digital Art.