An adaptation of William Shakespeare's Twelfth Night, the film was directed by Andy Fickman, produced by Lauren Shuler Donner, Tom Rosenberg, and Gary Lucchesi, and was written by Karen McCullah Lutz and Kirsten Smith.
Amanda Bynes and Channing Tatum were cast respectively in the lead roles of Viola Hastings and Duke Orsino. Tatum had been chosen at Bynes' insistence, as she felt that he would be received well by audiences.[4] She told Paper in 2018 that "I totally fought for Channing [to get cast in] that movie because he wasn't famous yet," she said. "He'd just done a Mountain Dew commercial and I was like, 'This guy's a star—every girl will love him!' But [the producers] were like, 'He's so much older than all of you!' And I was like, 'It doesn't matter! Trust me!'"[5][4]
In order to prepare for the role, as it was her first time playing a role of the opposite sex, Bynes and Fickman observed males at a shopping mall.[6] In an interview with MSN in 2006, she said that the part had been difficult for her to play, stating that she felt "awkward" in the role; she later spoke highly of the experience, saying that "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."[6] However, in a 2018 interview with Paper, Bynes admitted that her role in the film eventually had a negative effect on her mental health. "When the movie came out and I saw it, I went into a deep depression for four to six months because I didn't like how I looked when I was a boy," Bynes said. Seeing herself onscreen with short hair, thick eyebrows, and sideburns was "a strange and out of body experience."[5]
Neither Bynes nor Tatum were skilled at soccer before filming, so they played the sport for hours each day to prepare for the role.[7] In a bathroom scene in the film, where a fight occurs between the characters of Bynes and actresses Laura Ramsey and Alexandra Breckenridge, some of the stunts performed had been done by the actors themselves. Fickman stated in a behind-the-scenes feature that "As much as we had our three wonderful stunt actresses there, too, when you see the cut of the movie, it's a lot of our girls pounding each other,".[6][8]
