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  1. A Dine-In Lottery Win. In 1984, New York City detective Robert Cunningham was dining at Sal’s Pizzeria in Yonkers when he suggested to his waitress and long-time friend Phyllis Penzo that the two split a lottery ticket instead of tipping on the bill. Though Robert was initially joking, Phyllis was hasty to agree.

  2. Mar 1, 2022 · In 1984, detective Robert Cunningham from Dobbs Ferry, New York, won a lottery payout and split it with his waitress, Phyllis Penzo, as he'd promised. In the movie, the cop promises to split because he has no money for a tip; in real life, Cunningham promised it because Penzo helped him pick the numbers.

  3. Dec 31, 1998 · Did a waitress receive a winning lottery ticket as a tip? Become a Member ... Cunningham gave Penzo a tip of $142,857.50 a year for twenty years. ... "A $6M Win and This Cop Went Hollywood ...

  4. Apr 2, 1984 · April 2, 1984. Waitress gets $3 million tip. YONKERS, N.Y. -- Police Sgt. Robert Cunningham offered a waitress at his favorite pizzeria half of his lottery ticket instead of a tip. She accepted ...

  5. Feb 10, 2024 · Yes, ‘It Could Happen to You’ is partially based on a true story. Penned by the talented screenwriter Jane Anderson, the film takes inspiration from the life of Detective Robert Cunningham of Dobbs Ferry, who won $6 million at the New York State Lotto prize in 1984 and decided to give half of it to Phyllis Penzo, a waitress employed at Sal ...

  6. May 28, 1984 · TIME. May 28, 1984 12:00 AM EDT. Two weeks after Betty Gloss won $6 million in the Illinois lottery last October, a police officer carrying a birth certificate visited the home of the winner and ...

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  8. It Could Happen to You: Directed by Andrew Bergman. With Nicolas Cage, Bridget Fonda, Rosie Perez, Wendell Pierce. A police officer promises to share his lottery ticket with a waitress in lieu of a tip.