Following his role at the Wexner Center for the Arts, Simon began to organize video programming across institutions in Europe and New York. 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). In New York, Simon organized video programs including "Man Trouble," at Exit Art (1994), and "The Talking Cure," at Artists Space (1992), both New York. Much of these events consisted of video works by artists practicing at the time and capturing contemporary concerns of media, spectatorship, and activism. By the mid-90s, Simon was beginning to exhibit his own multimedia work in one-person exhibitions. In 1994, he presented "The Mayfair Show," at the Mayfair Club and at American Fine Arts, Co., both in New York. The exhibition focused on connections between artmaking and gambling through the lens of psychoanalysis, and would travel years later to Yale Union, Portland, OR, in 2016. 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. 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. In 1998, he presented his exhibition "Public Address: Collapsed" at Pat Hearn Gallery, a tableau with stadium-scale speaker horns resting on the gallery floor. 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." In the spring of 2005, Simon, along with a number of other collaborators, began to operate Orchard, a cooperatively run gallery in New York City's Lower East Side. Orchard's format was primarily to organize exhibitions of various artists by thematically connected groups, while also drawing links between different artistic generations and reintroducing lesser known historical artists or art projects. The project-space was intended to last for three years, and concluded in May of 2008. In April 2006, Jason Simon exhibited his film "Vera" at Orchard, which he shot in 2003. 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.