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During O'Brien's sentencing, the judge describes him as a sociopath. His behavior is undoubtedly antisocial, but he doesn't really fit the profile. His cellmate and friend, Horowitz (Eric Gurry) does however-- he is superficially charming, glib, highly intelligent, despises boredom and isolation and doesn't seem to have much remorse for the crimes he has committed. It is reasonable to see why O'Brien might be mistaken for a sociopath. He was raised in an unstable environment wherein a specific type of masculinity is the norm. Any showcase of weakness or emotion is perceived as effeminate or weak. Once he is imprisoned, the need to be as tough is possible is a necessity. A prisoner likely has to perform sociopathy in order to survive.
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O'Brien's street smarts work well for him inside. He begins to make a name for himself inside after he beats Lofgren and Tweety with a pillowcase filled with soda cans and becomes the leader in the prison. That is until Paco Moreno (Esai Morales), O'Brien's enemy from the outside ends up in the same prison. Undoubtedly, O'Brien and Morales have a huge confrontation at the end of the film. And it is long and violent and bloody. Though O'Brien walks away, having decided against killing Morales, Bad Boys doesn't neatly wrap up with O'Brien being rehabilitated and changing his life. It only shows him returning to his cell. The suggestion is that the specific type of masculinity that exists and is taught within prisons doesn't easily translate to a life outside.
The compelling aspect of this film is the way in which it presents the emotional awkwardness of young men. Any showcase of sensitivity in the prison, either through artistic expression or otherwise, is met with derision. When O'Brien receives upsetting news about his girlfriend, he says he "feels like crying," but does not. Emotional pain is channeled through violence. In a way, the prison becomes a metaphor for trapped emotions as it is only when O'Brien is momentarily out of the prison that he breaks down. It is worth noting that the very idea that any emotion or hesitation is equated with effeminacy is what lead O'Brien to prison to begin with; and, that within the prison walls, the only acceptable way to express any emotion is rage which leads to violence which leads to a longer sentence.
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