Steve James' affiliation with Kartemquin began in 1987 with the start of production of Hoop Dreams, for which he served as director, producer, and co-editor. He has since then become one of the most acclaimed documentary makers of his generation, with noted works being Stevie, The New Americans, The War Tapes, At the Death House Door, The Interrupters, Life Itself, and most recently the 2018 Academy Award®-nominated Abacus: Small Enough to Jail.

Steve's first film Hoop Dreams won every major critics award in 1994 as well as a Peabody and Robert F. Kennedy Journalism Award in 1995. The film earned James the Directors Guild of America Award and the MTV Movie Award’s "Best New Filmmaker." Recently, Hoop Dreams was selected for the Library of Congress’ National Film Registry, signifying the film’s enduring importance to American film history, and hailed by critic Roger Ebert as, "the great American documentary."

James' next documentary, Stevie, won major festival awards at Sundance, Amsterdam, Yamagata and Philadelphia, and was nominated for an Independent Spirit Award. The acclaimed feature landed on a dozen "Top Ten Films of the Year" lists for 2003. James was also an executive producer, story director, and co-editor of the PBS series, The New Americans, which won two Chicago International Television Festival Golden Hugos, and the prestigious 2004 International Documentary Association Award for Best Limited Series for Television. In 2005, James completed the documentary Reel Paradise, his fourth film to premiere at the Sundance Film Festival. James then served as producer and editor of The War Tapes, a documentary comprised of video footage shot by American soldiers in Iraq. The film won the top prize at both the 2006 Tribeca Film Festival, and the inaugural 2006 BritDoc Film Festival.

In 2008, he co-produced and co-directed with Peter Gilbert the acclaimed At the Death House Door, which won the top prize at the Atlanta Film Festival, the Inspiration Award at the Full Frame Documentary Film Festival, and aired on IFC-TV. At the Death House Door is James’ fourth film to be officially short-listed for the Academy Award. 

James' 2010 documentary No Crossover: The Trial of Allen Iverson had its world premiere at the SXSW Film Festival and aired as part of ESPN Films' 2010 International Documentary Association award-winning series 30 for 30. The film was selected for the IDOCS International Documentary Forum in Beijing, and also played at the Cleveland, Full Frame, Dallas, Nashville and Atlanta film festivals, among others, as well as earning James the Best Director award at the Midwest Film Awards. In 2011, No Crossover was selected by the U.S. Department of State for the American Documentary Showcase.

In 2011 James released his sixth film in partnership with Kartemquin, The Interrupters. Marking a return to some of the same Chicago neighborhoods featured in Hoop Dreams, James co-produced the film with acclaimed writer Alex Kotlowitz (There Are No Children Here). The film was his fifth feature to be selected for the Sundance Film Festival, and was a hit on the festival circuit winning a dozen awards including the grand jury prizes at the Sheffield Film Festival, Miami Film Festival, and Minneapolis Film Festival.  It won both the IndieWire and Village Voice’s national critics polls as the best documentary of the year, and was listed on over 60 “Best Films of the Year” lists including Time, The New Yorker, The Chicago Tribune, Boston Globe, and The LA Times among others.  James won the two top prizes at the 2012 Cinema Eye Honors – “Nonfiction Feature Filmmaking" & "Best Direction" – and was nominated for the DGA Award (his third DGA nomination). The Interrupters also won the 2012 Independent Spirit Award, and Emmy, and the duPont-Columbia Journalism Award.

James' 2014 film Life Itself, about film critic Roger Ebert, premiered to critical acclaim at Sundance and was named the best documentary of the year by over a dozen critics associations, and received the Golden Tomato Award from RottenTomatoes.com as the best reviewed documentary of 2014. It also was awarded best documentary by The Critic’s Choice Awards, The National Board of Review, and The Producers Guild of America.

In 2017 James released Abacus: Small Enough to Jail, which received an Academy Award® nomination for Best Documentary Feature. It won Best Editing: Documentary Feature at the Ashland Film Festival, Best Political Documentary at the Critics' Choice Documentary Awards and earned James a nomination for the Directors Guild of America Award for Outstanding Directing. Critics hailed Abacus as a "classic underdog tale" (New York Times) and "an exemplary piece of filmmaking" (Sight & Sound).

James’ dramatic films include the theatrical feature Prefontaine (1997), which premiered at Sundance, and cable movies Passing Glory (1999) and Joe and Max (2002), which was nominated for an ESPN Espy Award.

The latest work by James, a 10 part docu-series entitled America to Me, world premiered its first five episodes at the 2018 Sundance Film Festival as the opening night film for the fest's inaugural Indie Episodic program. Daniel Fienberg wrote of the 'sneak peek' of the series, "I suspect that America to Me will end up being one of the year's best shows of any kind." The series is a year-long immersion into one of Chicago's most progressive and diverse public schools, located in suburban Oak Park. Following its Sundance premiere, America to Me was acquired by STARZ and will premiere in full in the fall of 2018.

His current projects at Kartemquin include serving as consulting director and executive producer on Generation Food, co-directed by Raj Patel and Zak Piper.