Matthew Perry Called His Whole Nine Yards Co-Star Bruce Willis 'The Coolest Man' He's Met

"Friends" star Matthew Perry acted alongside some of the biggest names in Hollywood before his tragic death on October 28, 2023, at the age of 54. Perry's roles — primarily in comedies — set the tone for his sprawling career. In one of these appearances, he starred alongside an actor whom he would later praise for his sheer coolness.

Perry starred alongside Bruce Willis in "The Whole Nine Yards," a 2000 action-comedy flick that also starred Amanda Peet and Michael Clarke Duncan. Perry played Nicholas "Oz" Oseransky, a dentist who is surprised to learn that his new neighbor is contract killer Jimmy "The Tulip" Tudeski (Willis). This wouldn't be the only time the duo would star alongside each other, however, as Willis would also land a guest role in "Friends" that would earn him an Emmy in 2000.

The two actors developed a strong relationship during their time starring opposite one another in the film and on "Friends." This was evident following the 2022 announcement that Willis was suffering from aphasia. Perry tweeted his support for Willis and gave him perhaps the greatest compliment any actor could offer one of their colleagues.

"Dear Bruce Willis, I'm so sorry to hear what you are going through, but you're still the coolest man I've met in my entire life," Perry tweeted. "You will remain in my prayers for a long long time."

Matthew Perry later opened up more on his relationship with Bruce Willis in his 2022 book, "Friends, Lovers, and the Big Terrible Thing." Perry noted that during his time working with Willis during the production of "The Whole Nine Yards," the two spent time partying together. This experience gave Perry an interesting insight into Willis' personality.

"But there was a big difference between Bruce and me," Perry wrote (via EW). "Bruce was a partier; I was an addict. Bruce has an on-off button. He can party like crazy, then get a script like 'The Sixth Sense' and stop the partying and nail the movie sober. He doesn't have the gene — he's not an addict."

Still, Perry notes that the two spent plenty of time together during the production of the film — especially after the parties had ended. This gave Perry a valuable chance to learn what kind of person Willis is when the cameras are turned off. "That's when I saw the real Bruce Willis — a good-hearted man, a caring man, selfless," Perry wrote. "A wonderful parent. And a wonderful actor. And most important, a good guy."

Perry also revealed in his book that while his relationship with Willis did not carry on much past his work with the star in 2000, the actor still held a special place in his heart. "I, of course, pray for him every night now," Perry wrote.