The Loop (2006)

Recently graduated Sam Sullivan is the youngest executive in crude Russ's airline's Chicago HQ. Sam's ruthlessly ambitious direct chief, feminist Meryl, considers him a sexually desirable toy and fun to abuse because of his noble naiveté. Sam's brother, screw-up Sully, doesn't just live in his flat as a useless parasite, he compounds surprising problems, usually at some point also dumped on Sam.

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