8. Olivia Thirlby
Movie: The Wackness (2008)
With the film set in the summer of '94 and scored to a cassette tape soundtrack of early 90s hip hop, Olivia Thirlby is essentially a a cross between a hippie and a fly girl. She offers free love (in the form of volunteering to take her dealer's virginity), tokes up regularly and dances in a jean jacket and hoop earrings in her dealer's music video-esque dreams.