His first paid film work was writing for the low-budget horror film Piranha (1978). Being on the set gave him his first taste of film production, working for and learning from legendary producer Roger Corman, and picking up tips from the director, Joe Dante. The following year Sayles directed his first film, Return of the Secaucus Seven (1979) on a $30,000 budget over 25 days. Sayles continued a long career as a screenwriter and director, only directing films that he has written, among them; Lianna (1983), The Brother From Another Planet (1984), Matewan (1987), City of Hope (1991), Passion Fish (1992) The Secret of Roan Inish (1994), Lone Star (1996), Men with Guns (1997), Sunshine State (2002) Silver City (2004), Honeydripper (2007) and Amigo (2010).
Aside from directing films, Sayles is also accomplished in the world of music videos, directing Bruce Springsteen in "Born in the U.S.A.," "I'm on Fire," and "Glory Days." Sayles was also a director, writer and producer on the television series Shannon’s Deal (1990-91), directing and writing the two-hour pilot. Known for shooting on location, acting in many of his films, and working on a tight budget, Sayles continues to direct, produce and write independent films to critical acclaim. He has been nominated for two Best Screenplay Oscars for Lone Star (1996) and Passion Fish (1992).