I would marry the real-life incarnations of you three in a heartbeat:
3. Jennifer Connelly in The Rocketeer
2. Winona Ryder in Reality Bites
1. Scarlett Johansson in Lost In Translation
Honorable Mentions: Rachel McAdams in The Notebook, Katherine Ross in The Graduate, Heather Graham in Swingers, Keira Knightley in Pride & Prejudice.