Benning experienced a political awakening and racial consciousness during the late 1960s, participating in civil rights protests led by Father James Groppi in segregated Milwaukee.

In 1980, Benning moved to lower Manhattan, where, with the aid of grants and funding from German Television, he continued to make films, most notably, American Dreams (1984) and Landscape Suicide (1986).

In the early 1990s Benning made a series of text/image films: North on Evers (1991), Deseret (1995), Four Corners (1997), and UTOPIA (1998), often invoking histories of how antagonistic cultural and economic agendas over land use shape landscapes and configure social environments.

Benning has employed diverse methods, themes, structures, and aesthetics, investigating narrative and anti-narrative modes, personal history, race, collective memory, place, industry, and landscape.

Nightfall (2012) consists of a single 98-minute shot made at a high elevation in the woods in the west Sierras that begins in late afternoon as the sun is going down and ends in near blackness.

Benning's use of duration reflects his accord with Henry David Thoreau's passage from Walden, "No method nor discipline can supersede the necessity of being forever on the alert.

Inside the cabins Benning has installed a number of copies he made of paintings by artists that have deeply inspired him, including Bill Traylor, Henry Darger, and Mose Tolliver.

In 2007, the Austrian Film Museum also published the first substantial monograph on the filmmaker, James Benning, edited by Barbara Pichler and Claudia Slanar.

Digital filmmaking allowed him to branch out in different directions including re-makes of Faces (2011) and Easy Rider (2012), as well as the two-hour one shot film Nightfall (2011).