1. Joe Mantegna, Adrien Brody, and Ben Foster as the Kurtzmans in Liberty Heights (1999)
Notable Jewish Moment: The film ends in a synagogue, during the high holidays. If that isn't Jewish, not much is.
Classic Quote: [Nate, to his wife, about his son, who is dressed up for Halloween.] "I wanna talk to Hitler. Put the Führer on the phone!"
Because picking one was too hard. Three generations of Jewish men, played by three solid actors, in one incredible 1960s period piece, all with their own problems.
There's Ben Foster, playing teenager Ben Kurtzman, who starts the movie by dressing up as Hitler for Halloween, and his rebellious trouble doesn't end until long after he decides to go on a mixed-race date to a James Brown concert. And then you've got Joe Mantegna as Nate, the loveable patriarch with the troubled number-running racket, whose charm has kept him away from competition and cops. Finally, Adrian Brody, who may have won his Oscar for The Pianist, but ends up being the heart of the Kurtzman clan as Van, who's just another Jewish kid in college trying to win the heart of a blonde-haired, blue-eyed W.A.S.P.
The real trick here? Whether you;re Jewish or not, by the end of Liberty Heights the three actors have made you feel like you're a distant relative, in that there's always a Kurtzman you can relate with.
Honorable Mention: Bebe Neuwirth as the mother of the Kurtzman clan.