Two films that explore faith as well as representations of good and evil that endure through generations — it's The Exorcist vs Enchanted.
Cruel to Be Kind: 10 Things I Hate About You vs 27 Dresses
Two movies about women who have always seen themselves a certain way but who are changed for the better after suffering through trickery and misunderstanding with their love interests — it's 10 Things I Hate About You vs 27 Dresses.