These best Ben Stiller and Owen Wilson movies are mostly funny, maybe not so much “Permanent Midnight,” but that was a strong film nonetheless. Both actors have been in some pretty awful films separately (we’re looking at you, “Duplex” and “Marmaduke”), but when put together, Ben Stiller and Owen Wilson are usually a pretty entertaining team.
- “The Royal Tenenbaums.” By far the best movie to feature both Ben Stiller and Owen Wilson, “The Royal Tenenbaums” was directed by Wes Anderson, narrated by Alec Baldwin, and featured Gene Hackman and Anjelica Huston as the heads of the titular family. Funny, quirky, and sad all at the same time, the movie has arguably been Anderson’s best to date.
- “Permanent Midnight.” The one movie on the list that doesn’t have much of a comedy element to it (although his scene with "Mr. Chompers" was pretty hilarious, in a frightening sort of way), “Permanent Midnight” starred Ben Stiller as real-life writer Jerry Stahl and is based on Stahl’s memoir of the same name. Owen Wilson played a smaller role as Stahl’s friend "Nicky". It was an uncharacteristically bleak movie for the two actors, but it is still one of the best Ben Stiller and Owen Wilson Movies.
- “Meet the Parents.” This movie was significantly less bleak than “Permanent Midnight,” with the exception of some pretty painful scenes at the expense of Ben Stiller’s character. Owen Wilson played a memorable roll as the seemingly beyond reproach ex-boyfriend of Stiller’s fiancée, and when the two clashed on screen it was comedic gold.
- “Starsky & Hutch.” Ben Stiller and Owen Wilson starred as the titular duo in this remake of the campy ‘70s television series. The jokes were often hit or miss, but any movie with Snoop Dogg as "Huggy Bear" is OK in our book.
- “The Cable Guy.” This criminally underrated comedy was directed by Ben Stiller and had brief cameos by both him and Wilson. The movie starred Jim Carrey and many were turned off by the fact that he didn’t talk out of his rear end like in “Ace Ventura: Pet Detective.” As far as we’re concerned, though, “Ace Ventura” has nothing on this biting social satire of a nation obsessed with television. Although they only appeared in it briefly, it is still one of the best Ben Stiller and Owen Wilson movies.