Waitress Gets $3 Million Tip from Lottery Winner

By Nicholas Christensen
Last Updated: May 5, 2019

In the 1994 romantic-comedy It Could Happen to You, a New York City cop (portrayed by Nicolas Cage) wins big at the lottery and splits the prize with his waitress friend (portrayed by Bridget Fonda).

It was a hit with audiences, and would definitely be one of the most interesting stories in lottery if it wasn’t fictional.

But did you know that it wasn’t entirely all made up?

The main premise – wherein a waitress receives a winning lottery ticket as a tip – that actually happened!

This is the true story of Robert Cunningham and Phyllis Penzo – the real-life inspirations for the main characters of the hit movie.

Screen grab from the movie It Could Happen to You
A still from It Could Happen to You

$ 53,000,000
Next Drawing
$ 168,000,000
Next Drawing

Robert Cunningham and Phyllis Penzo

In 1984, New York City police detective Robert Cunningham was at South Pizzeria in Yonkers when he jokingly asked waitress Phyllis Penzo if they could split a lottery ticket instead of tipping her. He promised to split the winnings between them if he won.

Cunningham and Penzo had been friends for 15 years at that point, so some friendly ribbing wasn’t unusual. But, even if it was said in jest, both took it seriously. Penzo agreed and even helped Cunningham choose the numbers.

Can you guess what happened next?

Raking it In

On April Fool’s Day, at 9:00 am, Penzo received the call that would change her life. It was Cunningham, calling to give her the big news – they had just won $6 million!

She didn’t believe it at first because she was still half-asleep and, well, because it was April Fool’s Day! However, Cunningham managed to convince her and once the news finally sank in, Penzo screamed and woke her husband.

True to his word, Cunningham split the winnings between them right down the middle.

Their haul? $287,715 annually for 21 years, each.

Robert Cunningham and Phyllis Penzo
Cunningham and Penzo appear in a lottery commercial

Cunningham added on to the house that he and his family shared with his wife’s parents. Penzo bought a house, a car for her husband and her daughter, and traveled a bit.

$ 53,000,000
Next Drawing
$ 168,000,000
Next Drawing

Reality or Fiction?

In It Could Happen to You, strangers Charlie and Yvonne are both married to unbearable, self-centered people, and they find solace in each other amidst their turbulent personal lives.

Spoiler alert: Both protagonists end up divorcing their respective partners and end up marrying each other instead, living happily ever after.

However, the only thing that It Could Happen to You got right about Cunningham and Penzo’s story is the core premise: a New York cop sharing a lottery win with a waitress.

Cunningham and Penzo were never a couple in real life. As mentioned earlier, they are long-time friends. They’re also happily married to other people.

There’s no sweep-you-off-your-feet romance. No antagonists making things hard for our heroes. No fairy tale ending. Cunningham and Penzo led very normal lives, all things considered.

Not as captivating as the movie’s plot, right?

Still, who knows – maybe one day you might just end up sharing a lottery win with a stranger, only to fall in love with them. Truth is sometimes stranger than fiction, after all – it could happen to you!