[3] Simon left his undergraduate studies in 1981 to work in Cambridge, MA, for Stuart Cody, an audio engineer associated with the ethnographic film and American Direct Cinema community there.
[5] This period resulted in his film and video projects Production Notes: Fast Food for Thought (1987), and Artful History: A Restoration Comedy (1987).
Programs such as "Downsizing the Image Factory" were screened at venues including Kunstverein München (1994), L'Unité d'Habitation, Firminy, France (1993), and Philadelphia Museum of Art (1995).
[4][11] As part of his representation with the Pat Hearn Gallery, Simon presented three solo exhibitions, one in 1994 titled "Album," an arrangement of large-scale polaroid photographs.
[3] His 1996 exhibition at the gallery, entitled "Spirits," included a selection of hand-toned silver gelatin prints that depicted various sinewy, curvilinear representations of cigarette smoke.
Writing in the pages of Artforum, art historian George Baker likened the exhibition to "a scene of catastrophe," that "opened up a surprising number of reflections on contemporary sculptural production.
"[12] In the spring of 2005, Simon, along with several other collaborators, began operating Orchard, a cooperatively run gallery in New York City's Lower East Side.
The 25-minute video work is an interview with a woman named Vera that discusses her addiction to purchasing designer clothes and accessories, and the psychology of consumerism, debt and desire.
[14] From 2003 to 2012, with the artist Moyra Davey, Simon organized the "One-Minute Film Festival," an annual summer gathering in a barn in upstate New York.