Masterson's first film appearance was in The Stepford Wives at the age of eight, playing a daughter to her real-life father. 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. In 1985, she returned to cinema in Heaven Help Us as Danni, a courageous teen running the soda shop of her gravely depressed Dad. She appeared with Sean Penn and Christopher Walken in the film At Close Range as Brad Jr's girlfriend Terry, a film based on an actual rural Pennsylvania crime family led by Bruce Johnston, Sr. during the 1960s and 1970s. She later starred as the tomboyish drummer Watts in the teenage drama Some Kind of Wonderful. As a result, she is loosely connected with the Brat Pack. 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. 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. For her work in that film she received a "Best Supporting Actress" award from the National Board of Review of Motion Pictures.
1990s
Masterson continued acting in films and television during the 1990s. In 1991, she starred in Fried Green Tomatoes, a film based on the novelFried Green Tomatoes at the Whistle Stop Cafe. The film was well-received, with film critic Roger Ebert applauding Masterson's work. The following year she was invited to host Saturday Night Live. In 1993, she played opposite Johnny Depp in Benny & Joon as Joon, his mentally ill love interest. In 1994, she acted in Bad Girls, playing Anita Crown, a former prostitute, who joins with three other former prostitutes in traveling the Old West. In 1996, Masterson acted alongside Christian Slater in the romantic drama Bed of Roses.
2000s
Although Masterson carried on her work in the film industry, by 2000 she had made a move towards television. In 2001, she produced her own television series, Kate Brasher, which was canceled by CBS after six episodes. In 2004, Masterson played Dr. Helen Taussig in the Emmy and Peabody Award-winning HBO biographical drama Something the Lord Made. Between 2004 and 2007, she made five guest starring appearances on as Dr. Rebecca Hendrix. A decade later, she appeared in a recurring role as FBI director Eleanor Hirst in the second and third seasons of Blindspot. Masterson has appeared in Broadway theater productions, and was nominated for a 2003 Tony Award as "Best Featured Actress in a Musical" in the Maury Yeston musical Nine: The Musical, directed by David Leveaux. Masterson has narrated several audiobooks, including I See You Everywhere by Julia Glass, Book of the Dead by Patricia Cornwell, The Quickie by James Patterson and Look Again by Lisa Scottoline.
Directing
In May 1993, Masterson revealed she had written a screenplay for a film tentatively entitled Around the Block, a romantic comedy about a "woman who conquers her fears by becoming a singer"; in a cover story about Benny & Joons box office success, she told Entertainment Weekly she was going to direct it herself, with principal photography expected that autumn. In 2001, she began her directing career with a segment titled "The Other Side" in the television movie On the Edge. Masterson made her feature film directorial debut in 2007, with The Cake Eaters, which premiered at the Ft. Lauderdale International Film Festival as well as the Ashland Independent Film Festival where it received the 'Audience Award – Dramatic Feature' prize in 2008. Of her move to directing, Masterson said in an interview, "When I signed to do this, I wasn't scared but, yes, it was scary. I'm already 40, although we don't want to talk about that. In '92, I wrote my first screenplay, which I then was to direct, but I ended up taking an acting job because it takes forever to get a movie made."
Personal life
Masterson was married to George Carl Francisco from 1990 to 1992. Masterson was married to filmmaker Damon Santostefano from 2000 to 2004. In 2006, Masterson married actor Jeremy Davidson after they starred together in the 2004 stage production of Cat on a Hot Tin Roof. Masterson gave birth to their first child, a son named Phineas Bee Greenberg, on October 11, 2009. She gave birth to twins in August 2011, son Wilder Greenberg and daughter Clio Greenberg.
