James' career began with the release in 1994 of the award-winning documentary, Hoop Dreams. In 1997, James directed the feature film Prefontaine followed by the TV movies Passing Glory and Joe and Max. His next documentary film Stevie was released in 2002. The Interrupters, a portrayal of a year inside the lives of former gang members in Chicago who now intervene in violent conflicts, was released in 2011 after premiering at the Sundance Film Festival. The film was his sixth feature length collaboration with his long-time filmmaking home, the non-profit Chicago production studio Kartemquin Films. To date, James has had nine films or docuseries premiere at the Sundance Film Festival.
In 2016, James directed Abacus: Small Enough to Jail, which premiered at the Toronto Film Festival and went on to be nominated for an Academy Award, James' second nomination.
There've been many documentaries over the years that have powerfully impacted me. I think this one came along at the time when I was more interested in being a feature filmmaker than a documentary filmmaker. So it came along at the beginning of a process of moving from an interest in feature film to documentaries, and that's where my career has taken me. It came along at the right time for me. It helped me see, "Ah, this is more what I want to do."[4]
James pulls influence from the original definition of the term cinéma vérité as it applies to the Rouch/Morin method of filmmaking. As with Rouch and Morin, the "people on camera and we in the audience are continually reminded that a film is being made, that we are watching a film." We are reminded through James' presence on screen as well as his cinematic editing techniques, in order to obtain what he believes is a more accurate depiction of truth.[5]
^Elder, Robert K. (2011). The Film That Changed My Life: 30 Directors on Their Epiphanies in the Dark. Chicago Review Press. p. 113. ISBN9781556528255.