10 Things I Hate About You
Heath Ledger, Julia Stiles, Joseph Gordon-Levitt
A high-school boy, Cameron, cannot date Bianca until her anti-social older sister, Kat, has a boyfriend. So, Cameron pays a mysterious boy, Patrick, to charm Kat.
Why you'll love it
The film features a strong, independent female lead similar to the personas often found in Taylor Swift's music.
Pretty Woman
Richard Gere, Julia Roberts, Ralph Bellamy
A corporate raider hires a hooker to act as a business escort in Beverly Hills, California.
Why you'll love it
A romantic narrative that echoes the fairy-tale-like love stories Taylor Swift sometimes explores in her lyrics.
Clueless
Alicia Silverstone, Stacey Dash, Brittany Murphy
Shallow, rich and socially successful Cher is at the top of her Beverly Hills high school's pecking scale. Seeing herself as a matchmaker, Cher first coaxes two teachers into dating each other.
Why you'll love it
The movie's focus on young love and social status aligns with common themes in Taylor Swift's songs.
Reality Bites
Winona Ryder, Ethan Hawke, Janeane Garofalo
A documentary filmmaker and her fellow Generation X graduates face life after college, looking for work and love in Houston.
Why you'll love it
The film captures the essence of young adult angst and love, reminiscent of Taylor Swift's earlier works.
My Best Friend's Wedding
Julia Roberts, Dermot Mulroney, Cameron Diaz
When a woman's long-time friend reveals he's engaged, she realizes she loves him herself and sets out to get him, with only days before the wedding.
Why you'll love it
The complex relationships and romantic themes are akin to the storytelling found in Taylor Swift's music.