I have this friend who has this problem. He's never cool enough, and he constantly feels inadequate, like he'll never fit in those cool hipster circles. I—uh, I mean, my friend—was really down about this, so I told him to watch Bernardo Bertolucci's The Conformist to get some perspective.
See, in The Conformist—which was first released in 1970—Jean-Louis Trintignant plays Marcello Clerici. When Marcello was young, some pervert tried to molest him; even though he luckily escaped by shooting the guy, Marcello's perception of guilt surrounding the whole situation has led to a life where he, like my hipster wannabe friend, never feels like he fits in. So, of course, Marcello goes and joins the Italian Fascist party, and marries the most common girl he can find, Giulia (Stefania Sandrelli).
The Fascists take advantage of Marcello and Giulia's honeymoon in Paris by assigning Marcello to rub out his old anti-Fascist philosophy teacher, Professor Quadri (Enzo Tarascio). Marcello, fully conforming to the ideals of the Fascists, accepts the job without question, even though he realizes his honeymoon will probably be disrupted. Naturally, things go awry: Marcello becomes infatuated with Quadri's beautiful bisexual wife, Anna (Dominique Sanda); Anna, in turn, tries to seduce Giulia. The whole story is told through non-chronological flashbacks against the backdrop of Italy during the first half of the 20th century. More specifically, Marcello's inner struggle closely corresponds with the rise and fall of the Italian Fascist regime.
The Conformist is easily the most accessible of all of Bertolucci's (mostly avant-garde) films. Visually, it's stunning, dark, and moody; and contains a lot of brilliant scenes, including a dreamy, incredibly sensual tango sequence. Because of its accessibility, many critics have labeled The Conformist as an embrace of commercial cinema, and the film's widespread appeal actually caused a rift between Bertolucci and his former mentor, French filmmaker Jean-Luc Godard.
As for my friend, after watching The Conformist, he realized that he was just being lame, and stopped bitching about being cool. We all learned that there's nothing like seeing somebody worse off than you—preferably a confused Fascist—to make you feel better about yourself.