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Self-destructive womanizer Jack (Alino Giraldi) spends his days either doing drugs, drinking, hooking up with random women, or some combination of the three. His morals seem non-existent and the only person in his life he isn’t a complete jerk to is his pet cat. Things start to change when he meets Jasmine (Shannon Coulter), a woman who actually won’t do whatever Jack wants. He slowly begins to fall for her, but her intentions are mysterious. The closer Jack and Jasmine get, the further Jack pulls away from his friends. Just as his world seems to be coming together, everything really starts to fall apart.

Congratulations must be given to Jackie Boy writer and director Cody Campanale because he manages to make the audience actually feel something for the absolutely horrible character of Jack. Within the first 5 minutes of the film, Jack has done drugs, taken a random woman from the bar home, photographed her in the nude and then tweeted those same images out when he finds out she already has a boyfriend. It’s shocking that he doesn’t throw her out of the house in her underwear.

You won’t like Jack, and you probably shouldn’t, but somehow by the end you’ll feel bad for the guy. Perhaps that’s because Campanale basically unleashes hell on Jack. Even a man with no redeeming qualities deserves better than what Jack winds up with. Giraldi is fantastic in the lead and has great chemistry with Coulter, who is the one character who can take Jack down a peg.

While you start to see where things are heading, Campanale twists them into some very, very dark territory. It’s hard to watch and incredibly shocking, and as a warning, it just may turn some viewers off of Jackie Boy.