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.
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.