Played By: Adrian Grenier
Hottest Conquests: Mandy Moore (Mandy Moore), Sasha Grey (Sasha Grey), Amanda Daniels (Carla Gugino), Sophia Lear (Alice Eve)

Because it blurred the line between real-life Hollywood and a fictional one (the series was loosely based on the Tinseltown exploits of Mark Wahlberg, the show's executive producer), the producers of Entourage were often able to cast real-life movie stars as the love interests of fake movie star Vincent Chase (Adrian Grenier), including Mandy Moore as Mandy Moore, Vincent's co-star in the (not real) Aquaman franchise. Make sense?

In the show's seventh season, porn star-turned-sort-of-legit-actress Sasha Grey (also as herself) became one of Vincent's many bedmates. But (SPOILER ALERT!) monogamy ultimately won out on the show's eighth and final season, when Vinnie falls for Vanity Fair writer Sophia Lear (Alice Eve), who—ironically enough—writes a scathing story on the actor, calling him an "insecure womanizer." We guess that's what passes for a Hollywood ending nowadays.