Denise Warner
October 05, 2012 AT 02:00 PM EDT

Adrian Grenier is a big fan of the documentary Brooklyn Castle, which follows junior high chess champions from I.S. 318 in the New York City borough. In fact, he enjoyed it so much that the former Entourage star challenges one of the players, Pobo, to a game in Washington Square Park. His only request for Pobo? “Don’t embarrass me in front of the whole park.” So who prevails? See their games below!

Watch the trailer for Brooklyn Castle:

The film opens in theaters on Oct. 19.

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