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Great comedy often comes in duos. It’s true of classic comedy like Abbott and Costello, stoner comedy like that from Cheech and Chong, and modern-day comedy from the likes of Key and Peele.

A joke just lands better when you have someone who can help you hone it, and many of these comedic pairs have built on-screen chemistry and rapport that helps their laugh machine run smoothly. Even when it isn’t an official pairing, we find that many comedians work together on multiple projects. Once they’ve found the magic spark, they’ll do all they can to keep it alive. 

Ben Stiller and Owen Wilson are one such pair, and Stiller was so convinced that Wilson needed to be a part of his film project that he says he wouldn’t have made Zoolander without his funny partner. 

Ben Stiller and Owen Wilson have worked together many times

By this point, Stiller and Wilson have become an iconic duo who fans expect to see together, but that wasn’t yet true in 2001 when Zoolander appeared. They had made some films together prior to this hilarious film.

As ScreenRant reports, they both made appearances in 1996’s The Cable Guy, but neither was a headliner and Jim Carrey was definitely the comedic draw of the show. They also appeared together in Permanent Midnight, a 1998 film that tells the real-life tale of comedian Jerry Stahl and his heroin addiction — not exactly the funny fare the pair would become known for. 

By 2000, it was clear that the pair had hilarious chemistry. That’s the year that they both took on major roles in Meet the Parents — parts they would reprise for two sequels.

In 2001, they worked alongside one another in both The Royal Tenenbaums and Zoolander. Since Zoolander gave both men headlining roles, that’s the film that many see as their official premiere as a duo.

They would go on to star together in Starsky & Hutch (2004), Night at the Museum (2006) and its sequels, and Zoolander 2 (2016). 

‘Zoolander’ has lived on a comedic classic 

It’s been two decades since Zoolander premiered, and the film continues to be a favorite for many comedy fans. The plot sounds too ridiculous to work, but it’s the absurdity that gives the show its hilarious edge.

Stiller stars as Derek Zoolander, a model who has thrice won VH1’s male model of the year but has finally been upstaged by Hansel (Wilson). As he loses his claim to fame, the rest of his world falls apart with it. His friends vanish, and his father expresses his disappointment in Zoolander. 

At this moment,  Zoolander is at his most vulnerable and is hired by fashion guru Mugatu. Thinking he is rebuilding his life, Zoolander doesn’t realize he’s actually being brainwashed in a plot to kill the Prime Minister of Malaysia.

What follows is as ridiculous as it is hilarious, and the film has given fans plenty of quotable lines and memorable scenes. 

Ben Stiller would not have made ‘Zoolander’ without Owen Wilson

Owen Wilson and Ben Stiller in a scene from the film 'Zoolander', 2001.
Owen Wilson and Ben Stiller in a scene from the film ‘Zoolander’, 2001. | Paramount Pictures/Getty Images

Stiller was heavily involved with Zoolander. In addition to playing the title role, he was also the director and one of the writers on the script.

With that much creative control, it makes sense that he would also have a heavy hand in the casting decisions. He cast his own father in a role for the film, making it one of several times Ben Stiller and Jerry Stiller shared the set.  

He also wrote the part of Hansel especially for Owen Wilson. As Mental Floss explains, Stiller knew that Hansel could only be played by Wilson: “Owen was the most important casting to me in the movie because I think he is one of the funniest people around–and the part was written for him.”

In fact, Stiller doesn’t think he would have made the film at all if Wilson couldn’t have filled the part.