37,951 suggestions

Brittany Murphy
as Michaela Eckman in 10 Things I Hate About You (1999, genderswap)

Melanie Lynskey
as Michaela Eckman in 10 Things I Hate About You (1999, genderswap)

Katie Holmes
as Josie Donner in 10 Things I Hate About You (1999, genderswap)

Amy Irving
as Wendy Stratford in 10 Things I Hate About You (1999, genderswap)
Carol Kane
as Wendy Stratford in 10 Things I Hate About You (1999, genderswap)

Rachael Leigh Cook
as Josie Donner in 10 Things I Hate About You (1999, genderswap)

Jennifer Love Hewitt
as Josie Donner in 10 Things I Hate About You (1999, genderswap)

Jodi Lyn O'Keefe
as Josie Donner in 10 Things I Hate About You (1999, genderswap)

Michael Pitt
as Brad Stratford in 10 Things I Hate About You (1999, genderswap)
Zachary Ty Bryan
as Brad Stratford in 10 Things I Hate About You (1999, genderswap)

Jonathan Taylor Thomas
as Brad Stratford in 10 Things I Hate About You (1999, genderswap)

Ryan Gosling
as Knox Stratford in 10 Things I Hate About You (1999, genderswap)

Hayden Christensen
as Knox Stratford in 10 Things I Hate About You (1999, genderswap)

Justin Timberlake
as Brad Stratford in 10 Things I Hate About You (1999, genderswap)

Ryan Gosling
as Brad Stratford in 10 Things I Hate About You (1999, genderswap)

Jamie-Lynn Sigler
as Cameron James in 10 Things I Hate About You (1999, genderswap)

Mila Kunis
as Cameron James in 10 Things I Hate About You (1999, genderswap)

Lacey Chabert
as Cameron James in 10 Things I Hate About You (1999, genderswap)

Christina Ricci
as Cameron James in 10 Things I Hate About You (1999, genderswap)

Brittany Murphy
as Patricia Verona in 10 Things I Hate About You (1999, genderswap)