His art is typically created through a series of self-imposed constraints also sometimes referred to as visual algorithms—rules Siena decides on before sitting down to work.
[8] Asked to name the teacher who most influenced him, Siena quickly cites Mary Croston, an after-school art instructor who taught him as a teenager.
[9] Croston treated her young students as “real” artists, says Siena, introducing them to such tools as charcoal and graphite and coaching them in figure drawing.
According to Siena, “He was a marvelous Renaissance man” who taught his students such skills as determining whether paper is archival quality and making ink out of toast crumbs and saliva.
[12] Prior to becoming an established and recognized visual artist, James Siena was known for his performance art, which included singing and rapping with his now ex-wife Iris Rose[13] and Chazz Dean.
[14][failed verification] Siena started making abstract paintings with an aesthetic that sought inspiration from Artificial Intelligence (AI).
… [He] balances the traditions of 20th–21st century abstraction with a maverick sensibility to craft salient, if speculative, insights on the contemporary world, and the intricate workings of human perception.
"[16]Siena has also played muse for other artists including being a subject for paintings and sculpture by Joe Fig[17] and multiple works of art by Chuck Close.
He completed a residence in October 2012 as the Arthur L. and Sheila Prensky Island Press Visiting Artist at Washington University in St. Louis.
In addition to his paintings and sculpture, Siena has made over 120 prints using a variety of techniques in collaboration with some of the most recognized art presses in the United States and abroad; including Universal Limited Art Editions (ULAE),[23] Tamarind Institute,[24] Harlan & Weaver, Flying Horse Editions, Pace Prints and Polígrafa Obra Gráfica.
The first, a collection of poems by Geoffrey Young, first published in 1996, "Pockets of Wheat" contains camera reduction images of James Siena's intricate 60" X 40" black-and-white ink drawings, including the cover illustration.
In 2003, Siena also contributed artwork to another book of poems by Geoffrey Young, entitled "Lights Out", published by the small press, The Figures.
- James SienaAlso in 2009 Siena created "Sequence", published and printed by Flying Horse Editions, a hand-printed, double-sided accordion book that stretches seventeen-feet long.
The double-sided book follows a linear, geometric pattern as it coalesces and unwinds through thirty-six pages, black intertwining with red, and in reverse.
The abstraction climaxes on two final frames (back and front), where the sequence reaches its full realization and the rule is maximized, having gone through seventeen 'moves.'
He worked with Ruth Lingen at Pace Prints (Pace Gallery represents James), and they came up with a label, now our reserve label, that incorporates letterpress fonts from the 19th century and a ‘necker’ with the vintage... Best of all, James redesigned our logo based on the word Illahe from the Duployan script that Merry Young found for the winery.
"[35]The art gallery BravinLee has also issued two series of hand-knotted wool rugs based on James Siena designs.
"[38] Artists whose work has been shown at the gallery include, David Brody, Tim Maul, Aura Rosenberg, Dan Schmidt, Peter Scott, and Fred Valentine.
In 2012, UrbanArias, a local Washington DC–based company that specializes in small-scale, contemporary, and experimental operas staged a production of Photo Op.
UrbanArias’ producer/conductor Robert Wood notes that, although Siena and Cummings wrote Photo Op in 1989, “the immediacy of this opera 20 years later is uncanny.” That's because it's so clichéd.
[42] Siena splits his time between homes in western Massachusetts (the Berkshires) and New York City and maintains a studio on Canal Street.