Hollywood may not be the best place to foster friendships, but some people really do make lifelong friends on the movie sets of Tinseltown. And if there’s one thing that fans love to see more than their favorite celebrities working together in film and television, it’s their favorite celebs becoming besties in real life. One of the few details we know about Owen Wilson’s life is that he is a frequent collaborator of Ben Stiller.
The two actors, who are each worth millions, have been working together since the 1990s, constantly appearing in hilarious comedy titles together. Their best-known collaboration might be Zoolander, but the pair have also worked together in a string of other hit films, including Starsky & Hutch and the Night at the Museum franchise. After seeing their amazing on-screen chemistry, fans can’t help but wonder if they are actually friends in real life, or if it’s all an act. Read on to find out where these two stars stand in real life.
Updated February 15th, 2023: This article has been updated to reflect new sources of information and to add a recent story about Ben and Owen's hilarious friendship.
Ben Stiller Reached Out To Owen Wilson First
The friendship and working relationship between Ben Stiller and Owen Wilson began in the 1990s. Before they had worked together, Stiller actually reached out to Ben after having seen his work to let him know that he was a fan.
“I think it was when he saw Bottle Rocket,” Wilson said of the first time Stiller reached out to him. “He wrote me the nicest letter, saying how much he loved the movie, which meant a great deal, because no one saw Bottle Rocket."
Wilson added that, in the letter, Stiller said, “’he hoped [they] might work together on something, some day,’ and that sure came to pass."
Ben Stiller is protective of Owen Wilson and looks out for his friend, admitting in interviews that he won’t go into detail about Wilson’s private life.
“I sort of like to protect his privacy, ‘cause I feel like it’s his own thing,” Stiller told Ellen DeGeneres. “But he's a really good friend of mine. He's an incredible guy and I wish him as everybody does, all the best."
At the time Stiller spoke to DeGeneres, Wilson had reportedly been hospitalized following a self-harm attempt.
Are Owen Wilson And Ben Stiller Still Close Today?
Although he hasn’t spoken about his friendship with Stiller in great detail, Wilson has opened up about it on occasion. Wilson admitted that the friendship dynamic between Stiller and himself hasn’t changed much since they first became friends.
“I don't know if the relationship has developed over time. It's a little like these characters [in Zoolander]. There isn't a big arc. From when we first became friends, walking around New York, I think that we are still sort of laughing at the same things and our dynamic is still pretty similar."
Like in many friendships, Owen Wilson and Ben Stiller still maintain their independence and don’t share every detail of their lives with each other. Talking to the press, Stiller has confirmed that there are still things he doesn’t know about Wilson.
“He lives this life that’s kind of mysterious in a way,” Stiller explained (via Hollywood Reporter). “I find it mysterious. I don’t think you could ever fully know him.”
Ben Stiller Is Always In Owen Wilson's Corner
What's interesting is that the two almost didn't even become as close as they are; Owen was nearly replaced in Zoolander back in the day. Luckily. Owen and Ben were a perfect match.
One of the hallmark signs of a healthy friendship is giving each other the space and freedom to make decisions, and supporting each other in those decisions. Stiller has been very supportive of Wilson throughout his career, even as Owen struggled, facing backlash from Marvel, among other issues.
Wilson was going to star in Stiller’s 2007 comedy Tropic Thunder—which was inspired by the ‘80s film Empire of the Sun and was also a satire of stereotypical Hollywood war and action movies. But Wilson dropped out due to personal reasons.
Stiller reportedly supported Wilson through that time and even helped him come to the decision, per People. In the end, Matthew McConaughey replaced Wilson in the film.
But Ben and Owen are still close; in an October 2022 interview, Ben explained that his daughter's friend found Owen Wilson's lost wallet one day, leading to the friend calling Ben up to get Wilson his wallet back.
Stiller, of course, blackmailed Wilson over the wallet, but it was all in jest. Clearly, the two remain on good terms, even though their initial collaboration feels like it was eons ago.
