10 Best Entourage Episodes
6. "Date Night"
The first season of Entourage is all about the up, and this is where things start to get real for Vince and the gang. His movie Head On is premiering, and the boys are in the mood to celebrate.
Only, no one told Eric, who has already made plans with Ari’s assistant Emily. While he’s hoping for some one on one time, the rest of the gang have other ideas, and quickly invite themselves along for a quadruple date.
The titular date night takes up the majority of the episode, and strikes the loose, enjoyable hangout vibe of early Entourage. Drama’s latest relationship with a tempestuous bodybuilder is played for strong laughs, and Turtle further ruins Eric’s plans for an intimate evening by inviting along a possibly crazed fan of Vince.
In typical Entourage fashion, the episode is built around the threat that Vince’s movie might not do well at the box office (spoiler alert: it does do well), and while there’s little doubt that Head On will be a success, the ending still packs some uplifting power.