Season 5, Episode 2
'Unlike a Virgin'
Vince is reading scripts, determined to find a new project, but everything he likes, Ari informs him, has already gone to Tobey Maguire or Leonardo DiCaprio. There is one script Eric found, Nine Brave Souls, but Ari refuses: No more indies. Eric, however, is interested in the writers (guest stars Giovanni Ribisi and Lukas Haas) and heads out to their office at the "Bullets and Bitches Artillery Club and Topless Bar" to discuss representing them.
Vince runs into Justine Chapin (guest star Leighton Meester), the young singer he had to pass up awhile back due to his firm policy. (Never be the first or the last.) When Justine invites Vince and the guys to her music video wrap party, Drama gets nervous that Jacqueline will know he's stepping out and works himself into a guilty frenzy that culminates in accusing Jaq of cheating on him, thus losing his girl.
At the party, Justine tries to pawn Vince off on a friend and Vince realizes just how far he's fallen. He demands an emergency meeting with Ari, vowing to do whatever it takes to act like a movie star again.