Michigan drops the game. Jerry and Marge drive 10 hour to Massachusetts to play Winfall. To boost their capital and increase their chances of winning, they meet Bill (Rainn Wilson), a convenience store proprietor.
In certain moments, “Jerry and Marge Go Large” feels like a heist movie without the crime. It plays as an anti-romantic comedy. The couple finds joy in the everyday and not in a frustrating, intractable journey. The film’s milquetoast Bonnie (Uly Schlesinger) and Clyde (Cheech Manohar) don’t go through without conflict. Act II introduces Tyler (Uly Schlesinger) to the role of a villain, along with Eric (Cheech Mohar), who are two arrogant Harvard students that also discover the loophole and form a betting organization of their own.
Eric hacks into the state lottery and discovers where Jerry and Marge are located. He and Tyler then pay a visit to the couple, interrupting their anniversary celebration. The youngsters are ageist and obnoxious, but slink from the store after Marge slyly offers the boys a juice box for the road and Jerry embarasses Tyler with his superior mathematical skills.