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The television show ‘Entourage’ has become a small phenomenon and it’s set to wrap up it’s 8 season run. It’s one of President Obama’s favorite shows, and true fans know the Hollywood super-agent Ari Gold character is based on the brother of former White House Chief of Staff and current Chicago Mayor, Rahm Emmanuel.

Like so many hair changes in TV history, Vince’s big haircut at the beginning of Entourage’s seventh season was so much more than just a trim. It’s actually his first step down the rabbit hole.

Before his disastrous breakup with Sasha, his fist fight with Eminem and his cocaine bust by the cops, Vince’s big cut was the biggest warning sign to his posse about what was to come. “This is his hardest season with what he’s going through,” star Kevin Connolly says in this exclusive clip from the Season 7 DVD. “He’s going through a battle that we’ve never seen him go through.”

The morning after the one-time Aquaman survives a near-death experience on the set of his latest movie, Vince wakes up a changed man — and in need of a new ‘do to go with his new ‘tude. “He’s been so managed and coifed and protected for so long that he’s forgotten to take risks,” star Adrian Grenier says. “As an actor, it’s really a joy to be able to look at the world in a new way.”

Entourage: The Complete Seventh Season hits stores on Tuesday, July 12.

Entourage returns for its eighth and final season on Sunday, July 24 at 10:30/9:30c on HBO.