In his 2022 autobiography Friends, Lovers, and the Big Terrible Thing, Matthew Perry recalled meeting Bruce Willis for the first time on the set of their hit 2000 comedy The Whole Nine Yards. According to Perry, he and Willis formed an unlikely bond considering that Perry was struggling with addictions to drugs and alcohol at the time, and Willis was a big partier. Despite that, production on the film went smoothly, and the pair’s first collaboration really delivered at the box office. Willis, however, didn’t have the highest hopes for it initially.

As Perry went on to explain, he was so confident that The Whole Nine Yards would be successful that he bet Willis the movie would do well. If Willis lost the bet, he would have to make a guest appearance on Friends. Willis confirmed this in a 2018 video for Wired. As fate would have it, The Whole Nine Yards ended up being the number one movie in America three weeks in a row.

Because of that, Willis would show up as Paul Stevens, the father of Ross’s girlfriend, Elizabeth, for a memorable three-episode story arc during Season 6 of Friends. Paul doesn’t approve of Ross and Elizabeth’s relationship because of their age difference, but Ross is determined to win him over. Paul even has a brief fling with Rachel (Jennifer Aniston) at one point. Willis reportedly donated his paycheck for the gig to five of his favorite charities, and later won an Emmy for his performance. 

Of his time working with Willis, Perry wrote that he came to know Willis as a “good-hearted man, a caring man, selfless. A wonderful parent. A wonderful actor. And most important, a good guy.” “And if he wanted me to be,” Perry continued, “I would be his friend for life. But as is the way with so many of these things, our paths rarely crossed after that.” The two linked back up again for 2004’s The Whole Ten Yards, which didn’t do nearly as well as its predecessor.