I think he would amor Donnie Darko. Especially, for the one scene where Donnie talks about how the buscar for God is absurd if life means that every living creature dies alone. It's so heartbreaking when Donnie says, "I don't want to die alone." I could see House really connecting with the brilliant, brooding, and maladjusted Donnie Darko. Also Donnie is an anti-hero much like House, and also seems to see the truth in the world whereas others seem to be living in a trance. Donnie is also not afraid of authority o calling people out on their shit.
I think House would also enjoy The Prestige....
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