Steve James' 2002 classic premiered at IDFA, winning the Joris Ivens Award, and also won awards from the Sundance and Yamagata Film Festivals and was a Spirit Awards nominee. The film was distributed in theaters by Lionsgate and gained critical acclaim, and has since been hailed as one of the best documentaries of the 2000s by multiple critics.

In the film, Steve James returns to Pomona, a beautiful rural hamlet in Southern Illinois to reconnect with Stevie Fielding, for whom James once served as an advocate Big Brother. He finds that the once difficult, awkward child has become -- ten years later -- an angry and troubled young man. Part way through filming, Stevie is arrested and charged with a serious crime. He confesses to the crime and then later recants. The filmmaker himself is drawn into the film as he tries to sort out his own feelings, past and present, about Stevie and how to deal with him in the wake of his arrest. What was to be a modest profile of Stevie, turns into an intimate four and a half year chronicle of a dysfunctional family's struggle to heal. In an interview with Jennifer Merin, Steve James stated: "Stevie, which was the film I did after Hoop Dreams, was the hardest film I've ever made. Without question, the hardest. It probably will be the hardest film will I ever make. And, it's the most brutally honest film I've made…about me, about Stevie, about his family. So, in some ways, I'm more proud of that film because of all of that. Just that we got it made and the impact it had. People hate me for it. They think it's an exploitation. I can't help that. But, anyway, it's a harder film and a deeper film than Hoop Dreams." "Stevie is one of the most narratively and ethically complex docs ever. It’s incredibly rich and challenging and emotionally difficult. In short, it’s absolutely brilliant." — Christopher Campbell, IndieWIRE "Stevie emerges painfully but profoundly as one of the most unusual, if not absolutely unique, efforts in the field of nonfiction filmmaking." — Andrew Sarris, The New York Observer