The movie: The Internship (2013)
The player(s): Vince Vaughn and Owen Wilson

You can't have a truly successful man child duo without a few followers. In the case of The Internship, Billy (Vaughn) and Nick (Wilson) persuade a handful of their serious-minded twenty-something Google co-horts to spend a night out on the town, where they engage in all sorts of debaucherous (and drunken) fun.