Every Vince Vaughn And Owen Wilson Movie, Ranked

When it comes to all-time great comedy duos, there are some pairings that immediately spring to mind: Abbott and Costello, Keegan-Michael Key and Jordan Peele. And when it comes to dynamic twosomes from the 2000s, it didn't get any better than when Vince Vaughn and Owen Wilson were on the same billing.

They were part of a larger collective known affectionately as the "Frat Pack," which also included Ben Stiller, Will Ferrell, and Luke Wilson, to name a few. They would frequently appear in one another's movies, sometimes even in just a cameo capacity that would catch audiences by surprise. However, out of this group, Wilson and Vaughn became virtually synonymous with one another, even if they haven't done a film together in quite a while. 

Wilson works regularly, while some people may wonder what happened to Vince Vaughn, but people still look back fondly on the classic comedies they did together. It may be easy to assume there are a ton of Owen Wilson and Vince Vaughn movies out there, but the truth is they were in only four together. That's still enough for us to rank them based on looking at their critical receptions, in addition to our own personal preference. Even when the movies themselves weren't all that great, the chemistry between Wilson and Vaughn was undeniable. 

The aforementioned Frat Pack's heyday was a golden few years in the 2000s. By the time 2013 came around, comedy had changed significantly, and while those players were still popular, they had largely gone on to do their own things. This is just one reason why 2013's "The Internship," otherwise known as "that Google movie with Owen Wilson and Vince Vaughn," feels so out of place.

The pair play down-on-their-luck salesmen who apply to be Google interns, and the two immediately become fish out of water when it's obvious they have a lack of qualifications. Much like Wilson's and Vaughn's characters don't belong at Google, the film itself feels out of place, with comedic sensibilities the world has largely moved on from. It also doesn't help that the film largely feels like product placement to promote Google, with Brian D. Johnson of Maclean's Magazine writing, "One reason the comedy lacks edge is that Google's role verges on product placement, as the ideology of 'Googliness' — an official Google mantra — is embedded in the movie's aspirational message."

There are conflicting reports over how much control Google had over the film, but it does appear as though the creatives behind the film didn't necessarily want to bite the hand that fed them. It may have been fun if Google was willing to poke fun at itself a bit, but instead, audiences were left with a two-hour Google commercial. "The Internship" is the last movie Vaughn and Wilson have done together, so perhaps it functioned as a nail in the coffin for their working partnership.

Some may be surprised to learn 2004's "Starsky & Hutch" is one of the biggest Owen Wilson movies of all time financially, and that just goes to show the power of casting some funny actors getting extremely silly in a remake of a 1970s TV series — only this film sees Owen Wilson pair up with Ben Stiller to portray the titular duo. This time around, Vince Vaughn gets to play the big bad in the form of Mr. Reese Feldman, a drug kingpin who seeks to distribute a new kind of untraceable cocaine. 

As far as movies based on old TV shows, "Starsky & Hutch" is fairly harmless. It has some decent jokes and simultaneously works as a time capsule to both the 1970s, when the original show aired, and the comedic tastes of the early 2000s. Antonia Quirke of The London Evening Standard was mostly complimentary toward the film: "At a time when the Hollywood studios seem locked in a competition to see who can make and distribute the most witless spoofs, pastiches and tributes, along comes one that is genuinely funny."

Those looking for a comedic throwback in this day and age may still find some gems to mine out of "Starsky & Hutch," like Wilson and Stiller donning all sorts of wacky outfits to go undercover. Just be careful because after watching it, you may find yourself telling everyone to "do it." 

"Zoolander," released in 2001, was the first time Owen Wilson and Vince Vaughn were in a movie together, even though Vaughn himself is barely in the film. It was a common feature of the Frat Pack for famous actors to sometimes have incredibly minor roles, and that's what happens here, as Vaughn plays Derek Zoolander's (Ben Stiller) brother, Luke Zoolander, who works at a mine. Of course, Wilson needs no introduction in this film, as he's Derek's nemesis-turned-ally, Hansel. 

People may not immediately think of "Zoolander" as a true-blue Wilson and Vaughn project, but there's no denying it's outright hilarious. It's even an untold truth of "Zoolander" that while film critic Roger Ebert gave it a negative review upon release, he came around to liking it in the years after. And it's easy to see why audiences continue to rewatch it all these years later. From the freak gasoline fight accident to "but why male models," there are numerous memorable moments to make anyone laugh in their seat. That includes Ed Gonzalez of Slant Magazine: "It's a one-joke movie, but a funny one nonetheless."

"Zoolander" is a gold standard of the era. But with hardly any screen time for Vaughn, it can barely be considered a genuine Owen Wilson and Vince Vaughn movie. There's one flick that has "Zoolander" beat.

When people think about Owen Wilson and Vince Vaughn movies, let's not kid ourselves. The first one to come to mind isn't "The Internship" or "Starsky & Hutch," it's arguably the best comedy to come out of 2005 — "Wedding Crashers." It's an R-rated laugh fest about two best friends who crash weddings together but end up infiltrating deeper than ever before when John (Wilson) falls in love with Claire (Rachel McAdams) despite her being engaged to Sack (Bradley Cooper). There's a lot of star power in the film, which went on to gross $288 million at the box office. 

"Wedding Crashers" remains a high point for both Wilson's and Vaughn's filmographies, earning a 75% rating from critics on Rotten Tomatoes, and it had a can't-lose formula. With the electric chemistry between the two leads, mile-a-minute jokes, and actual sentiment beneath all of the bawdy humor, "Wedding Crashers" excels where so many other comedies fall short. It's a perfect showcase of why Wilson and Vaughn work so well together. Wilson has that more down-home sincerity, often serving as an ideal straight man for Vaughn's more outrageous sensibilities. 

Nearly 20 years later, the question remains as to whether we'll ever get to see a "Wedding Crashers" sequel. Even if that doesn't materialize, it would just be nice to see Wilson and Vaughn share the screen once more.