Superstar (1999)

Name: Superstar
Released: 1999

Orphan Mary Katherine Gallagher, an ugly duckling at St. Monica High School, has a dream: to be kissed soulfully. She decides she can realize this dream if she becomes a superstar, so her prayers, her fantasies and her conversations with her only friend focus on achieving super-stardom.

Genres: Comedy, Romance

What to watch after Superstar

Semi-Pro (2008) — Will Ferrell appears in both
Never Been Kissed (1999) — Molly Shannon appears in both
A Night at the Roxbury (1998) — Steve Koren wrote for both
54 (1998)
She's All That (1999)
Dream a Little Dream (1989)