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Throughout the film, Amanda Bynes' character Viola pretends to be her brother Sebastian, so when she was first cast, she was tasked with learning how to act like a guy. To prepare for the role, Bynes said she and director Andy Fickman went to a shopping mall to observe how men and women interacted. In a interview with MSN, Bynes said she knew she could do character work based on her time on "The Amanda Show," but pretending to be Sebastian was difficult for her because she felt awkward in the role. On stepping into a male role, she said, "It was hard, but I did it and I did something that was not easy for me — so it was a cathartic experience and I felt really good getting it out of me. In , Bynes told Paper magazine that watching herself acting as a boy sent her "into a deep depression" because she didn't like the way she looked.

Inspired by William Shakespeare 's play Twelfth Night , [3] the film centers on teenager Viola Hastings, who enters her brother's new boarding school, Illyria Prep, in his place and pretends to be a boy in order to play on the boys' soccer team. The film received mixed reviews from critics, but Bynes' performance was praised. Viola Hastings is a teen girl who plays for Cornwall's soccer team until the team gets cut. Her dream is to play for the North Carolina Tar Heels. Meanwhile, her twin brother, Sebastian James Kirk , is supposed to enroll in Illyria, an elite boarding school, but he secretly goes to London with his fledgling band instead.