The film was well-received, with film critic Roger Ebert applauding Masterson's work. In 1991, she starred in Fried Green Tomatoes, a film based on the novel Fried Green Tomatoes at the Whistle Stop Cafe. Masterson continued acting in films and television during the 1990s.
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For her work in that film she received a "Best Supporting Actress" award from the National Board of Review of Motion Pictures. In 1989, she played in Chances Are alongside Cybill Shepherd, Ryan O'Neal and Robert Downey Jr., and she starred as Lucy Moore, a teenage girl giving up her first baby to a wealthy couple, played by Glenn Close and James Woods in Immediate Family. The same year Francis Ford Coppola cast her in Gardens of Stone in which she acted with her parents who were hired by Coppola to play her on-screen parents. As a result, she is loosely connected with the Brat Pack. She later starred as the tomboyish drummer Watts in the teenage drama Some Kind of Wonderful (1987). She appeared with Sean Penn and Christopher Walken in the film At Close Range (1986) as Brad Jr's girlfriend Terry, a film based on an actual rural Pennsylvania crime family led by Bruce Johnston, Sr. In 1985, she returned to cinema in Heaven Help Us as Danni, a courageous teen running the soda shop of her gravely depressed Dad. Rather than continue her career as a child actor, she chose to continue her studies, although she did appear in several productions at the Dalton School.
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Masterson's first film appearance was in The Stepford Wives (1975) at the age of eight, playing a daughter to her real-life father. Later, she attended schools in New York, including eight months studying anthropology at New York University. As a teenager, she attended Stagedoor Manor Performing Arts Training Center in upstate New York with actors Robert Downey Jr. She has two siblings: Peter Jr., and Alexandra.
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Masterson was born June 28, 1966, in Manhattan (some sources cite Los Angeles, CA) the daughter of writer-director-actor-producer Peter Masterson and singer-actress Carlin Glynn.