Maggie Lawson in Cheats (2002)

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A close-knit group of teenage friends bands together to fake their way through high school in the clever teen comedy Cheats (2002). Trevor Fehrman stars as Handsome Davis, the ringleader of a disingenuous clique dedicated to passing exams without agreeing to a second of studying. Together with buddies Sammy (Elden Henson) and Victor (Matthew Lawrence), Handsome successfully pulls the wool over the eyes of his meddling principal, played by Mary Tyler Moore. Naturally this leaves the cheater with a bunch of extra time to chase skirts, which is exactly what he does. Maggie Lawson plays the object of Handsome’s affections--a pretty young thing with glasses and a hot bod to boot.