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It's mostly comedic but some takes look as if he really tears up pretty good, mostly the one at 0:32 which is comedic as well..
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There was a film and I think there also was a thread here about "I love you Philip Morris" where he cried too. If I remember right there was an interview where he talks about the crying scene and that he was able to produce tears quite effortlessly
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Thank you for reminding me about that, flatter. I was trying to find those scenes, i remembered having watched the movie a long time ago and i guess he cried the most in it..
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I also noticed that they omitted "I Love You Philip Morris", one of his legitimate (i.e. non-comedic) crying movies . (Though he is overshadowed by the brilliant waterworks of Ewan McGregor.)
"Eternal Sunshine" is a nice one too.
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Another great scene in Kidding :
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And a sobbing intense one here :