After Home Alone but before sext texts, there's still the part where he fucks Amanda Peet, gets beat up by Jeff Goldblum, rejected by Claire Daines and dumped on by Ryan Phillipe.
It's one of the hands down best films of this century, and I still think it's Culkin's finest work - he's so young and batting 100 against a seriously stacked cast. Aside from the wonderful "you roll vegan joints", this scene is just brilliant, both of them. That fucking laugh! https://youtu.be/nmZzVksrf4k
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https://youtu.be/nmZzVksrf4k
https://www.youtube.com/watch?v=DSnriG05QIY