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I'm positive this is from The Lake House, with Sandra Bullock. I saw it once a while ago but somehow didn't appreciate the crying enough to remember! He's lovely here. I love his little gasping sobs.
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John Wick ?
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Yes that’s the scene! The Lake House scene was good but this one is my fave of the two because we get to see him composing himself afterward. Plus I just love his look in John Wick, and imo the transition from not-crying to crying was smoother.
He does crying well when the tone of the scene is quiet. Like his acting. He does most of his best work when he can be quiet and subtle.