75. Jamie Lynn Sigler
Thanks to the epochal HBO series The Sopranos, the NYC native became the ultimate DILF: Daughter I'd Like to (De)Flower. We thought she'd fallen off the face of the earth until she joined the cast of Entourage to play Turtle's (played by her former real-life boyfriend Jerry Ferrara) girlfriend. It's like Chris Rock said after Janet Jackson got with Jermaine Dupri: We all had a chance!
DECADE ACHIEVEMENT: Two words: Meadow Soprano.