Skyler is the author of the play "The Moonlight Room", about at-risk youth in New York City, which she co-produced at the TriBeCa Playhouse in 2003 before transferring to a commercial run Off-Broadway on Theater Row. It was named one of the 'Ten Best Plays of the Year' by The New York Times and The New York Post, and has since been performed all over the country. Previously she co-wrote the feature film "Getting to Know You," directed by her sister, Lisanne Skyler, and adapted from short stories by Joyce Carol Oates. The film starred Zach Braff, Chris Noth, Heather Matarazzo and Bebe Neuwirth and premiered in the Dramatic Competition at the Sundance Film Festival, the 'Critics Week' section of the Venice Film Festivals, and received "Two Thumbs Up" from Ebert and Roeper.