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Italian American crime bosses Vito Genovese and Frank Costello, run their respective families during the 20th century. In 1957, Genovese tries (and fails) to assassinate Costello, who is ultimately injured and attempts to retire from the mafia.
Ben Stiller portrays risk-averse Reuben Feffer, whose best-laid plans for life and love careen wildly off track when his bride (Debra Messing) dumps him on their honeymoon for a muscle-bound scuba instructor (Hank Azaria). Stunned, humiliated and in the grip of acute indigestion, Reuben plans to play it safer than ever. But a chance encounter with an adventure-craving, childhood friend named Polly (Jennifer Aniston) shoots him into a whirlwind of extreme sports, spicy foods, ferrets, salsa dancing and living in the moment.