Jerry Selbee (Cranston) is retiring after more than five decades at the same Kellogg’s factory job. His section is being dissolved and he’s being sent off with the praise and plaudits of his superiors, and just enough retirement income to get by. But he’s restless, immediately looking for ways to keep occupied, and unhappy with the fishing boat that his family has gifted him as the solution. That’s when he stumbles upon the “Winfall” lottery, a special state lottery promotion that gives the player better odds to win. Normally this would never interest Jerry, who is so wary of gambling that he won’t even let his accountant (Larry Wilmore) invest his retirement savings in the stock market. But Jerry, you see, is a math genius. And Winfall is no gamble — it’s a sure deal to win millions of dollars based on a loophole in the system: the more you bet, the more you win.
Jerry starts off small at first, withdrawing a few thousand out of his bank account and making more back than even he anticipated. But his wife Marge (Bening) soon catches on, and rather than scold him for his questionably legal activities, she — eager to spend more time together with her husband in their “golden years” — wants in. Things escalate from there, and soon, the two of them have started a whole business enterprise that they loop a local drug store clerk (Rainn Wilson, sleazing it up) who mans the machine that prints their tickets into, along with their entire Michigan town. All…
