Masterson often worked with his cousin, writer Horton Foote. Acting from the mid-1960s to the mid-1980s,including 1975's The Stepford Wives as Walter Eberhart, since then he has concentrated mostly on directing and producing. His daughter is actress Mary Stuart Masterson, who appeared with her father in The Stepford Wives as one of the Eberhart's daughters.
Masterson's most well known and critically recognized work is The Trip to Bountiful. He wrote the books for the hit musical The Best Little Whorehouse in Texas and its short-lived sequel The Best Little Whorehouse Goes Public. His most recent work in film includes Night Game (1989) Lost Junction (2003) and Whiskey School (2005). Masterson has also been responsible for some theatrical disasters including Convicts. Convicts, starring James Earl Jones and Robert Duvall, went straight to video.
Masterson is also an accomplished sailor.
In 1989, he won the Silver Medal in World Championships 5.5 metre class in Houston.
He won the Silver Medal again for the 5.5 Metre Class in 1990 in Torquay.
He won the Silver Medal a third time in the 5.5 Metre Class in 1992 in Nassau.