Superstar (1999)

Orphaned after the death of her parents and raised by her strict grandmother (Glynis Johns), awkward Roman Catholic high-school student Mary Katherine Gallagher (Molly Shannon) dreams about dating popular student Sky Corrigan (Will Ferrell) and becoming a star. To achieve both goals, Mary enters a talent contest, where her competitor is Sky's girlfriend, Evian Graham (Elaine Hendrix). Despite her grandmother's opposition, Mary prepares to win both the contest and Sky's affection.