She's the Man (2006)

Synopsis
A simple case of assumed identity snowballs into a romantic mix-up of epic proportions in director Andy Fickman's contemporary teen take on William Shakespeare's Twelfth Night. Viola Hastings (Amanda Bynes) has good reason for wanting to conceal her identity upon arriving at Illyria Prep school, and with her twin brother Sebastian (James Kirk) skirting school in an attempt to break into the London music scene, Viola sees her sibling's well-timed absence as the perfect opportunity to assume his identity. When Viola is assigned a shared dorm room with campus cool guy Duke (Channing Tatum), her façade slowly begins to crumble as she begins harboring a deep-rooted crush on her unsuspecting new roommate. The situation begins to take a turn for the worse, however, when Duke reveals his affection towards campus knockout Olivia (Laura Ramsey), who in turn seems increasingly drawn toward the sensitive imposter known as Sebastian. The problem is, the real Sebastian has decided to cut his London trip short, and upon arriving on campus two days earlier than expected, Viola's elaborately executed ruse hits an unexpected hitch that sends the entire situation spiraling into chaos. ~ Jason Buchanan, All Movie Guide