Directing
By 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 & Joon's 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 awards for "Best Picture". 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."
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