The 2000 crime comedy The Whole Nine Yards is a bit of a mixed bag. Is it over the top? Yes. A little predictable? Sure. Despite its shortcomings, however, the unlikely combination of stoic Bruce Willis and sarcastic Matthew Perry led to a film largely enjoyed by mainstream audiences – and, due to Perry’s efforts to make the movie a success – an Emmy win for Willis.

Now, obviously, Emmys are awarded for excellence in the television industry. The Whole Nine Yards is a movie. How could a movie lead to an Emmy? Well, it all started with a bet between Matthew Perry and Bruce Willis on set.

Fresh off his The Sixth Sense success, Bruce Willis was looking for another Hollywood hit and signed on to The Whole Nine Yards. As Willis said himself in a 2000 interview on Larry King Live, the movie had a great cast. “I was surrounded by really funny people,” he said. “Matthew Perry is hilarious. Kevin Pollack, hilarious. You’re going to meet Michael Clarke Duncan, Amanda Peet. These guys were all just extremely funny. Everybody was — you know, the day players who came in, the two cops at the end, hilarious.”

As production got underway, however, Willis began to lose confidence in the film. He worried the “hilarious” cast wasn’t enough to make a successful movie. Sensing his costar’s hesitance, Matthew Perry made an effort to boost morale by proposing a bet. “Bruce hadn’t been sure the film would work at all, and I’d bet him it would — if he lost, he had to do a guest spot on ‘Friends,’” Perry recalled in his 2022 memoir Friends, Lovers, and the Big Terrible Thing.

Bruce Willis’ Bet With Matthew Perry Led to 3 ‘Friends’ Appearances and an Emmy

Well, The Whole Nine Yards went on to gross $106.4 million worldwide, vastly outweighing its $41 million budget, making the film a certified hit. And, true to his word, the legendary Bruce Willis appeared on Friends – not once but three times!

Friends fans will remember him well as the father of Ross’ college-aged girlfriend who goes on to date Rachel. Rachel spends the beginning of their relationship trying her hardest to get her intimidating new beau to open up. It eventually works, but Willis’ character cries on her lap one too many times and the pair go their separate ways.

Bruce Willis understandably never addressed the bet with Matthew Perry. Betting against your own movie isn’t the best look, after all. But Willis certainly doesn’t regret his Friends appearance, as he went on to win the Emmy for Outstanding Guest Actor in a Comedy Series for his work on the sitcom that year.

To make a happy ending even sweeter, Willis donated his appearance fee to charity, meaning he essentially did the Friends cameo for free. Bruce Willis and Matthew Perry remained friends until Perry’s death in October 2023.