Hey boy
here's a character in Yakuza 0 called Bacchus who has a voice line where he says "Hey boy" in a silly voice, which Joe liked to imitate.[1][2] Bacchus looks like a homeless person so sometimes Joe says this around homeless characters in games.
References
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“Falco” video: “Joseph Anderson Yakuza 0 stream 20 with chat [11/19/2020” at 01:35:44].
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“Falco” video: “Joseph Anderson Yakuza 0 stream 21 with chat [11/20/2020” at 06:39:17].