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Movies like Pluto (2011)

Pluto can't help himself. Adopting the roles of various men (and women) of different ages, statuses and personalities, Paul "Pluto" Strauss spends his daily life interfering with the lives of strangers. Having nothing better to do with his endless time and countless money, he escapes his own unhappy reality in pursuit of something a little more entertaining. While he is not harassing people he's never net, he spends the rest of his time inconveniencing (and often embarrassing) those closest to him. It is not until Olivia, a girl from his past, reenters his life that Pluto must acknowledge the weight of his lies and the consequences they bring.