Vince Vaughn and Owen Wilson

The 8 Funniest Comedy Duos in Hollywood

On screen, some stars just have chemistry. Since comedy is such a give-and-take, we’ll often see comedy actors collaborate with one another on several films. In this list, we’ll look at those duos that have made us laugh the most.

  1. Ben Stiller and Owen Wilson
    Years ago in an interview with Cinema Confidential, Ben Stiller said (of Owen Wilson): “We just enjoy each other's company and have fun working together. As long as people seem to allow us to work together, I think it will kind of keep going.” Thankfully, they HAVE been allowed to work together and, as of now, the two of them have appeared in 11 films with one another.

  2. Owen Wilson and Vince Vaughn
    Though they aren’t the same powerhouse duo that Wilson forms with Ben Stiller, Vince Vaughn and Owen Wilson have elicited their fair share of laughs as a comedy duo. Most notably in Wedding Crashers and The Internship.

  3. Will Ferrell and John C. Reilly
    These two have (so far) only appeared in two films together as leads. However, in both cases (Talladega Nights and Step Brothers), the films were extremely successful. Anyone who’s seen these films knew that these two would make the list. And, if you’re a fan, it should please you to know that these two will be starring together in a third film titled Border Guards.

  4. Simon Pegg and Nick Frost
    This duo began working together on the UK TV series Spaced, with director Edgar Wright who they’ve gone on to do three films with. Together, Frost and Pegg have starred in four films and their chemistry is apparent and entertaining throughout.

  5. Tina Fey and Amy Poehler
    Fey and Poehler have been working together for quite some time. They started doing improv comedy in Chicago and ended up on SNL together years later, eventually becoming co-anchors on the wildly popular Weekend Update segment of the show. After leaving SNL, the two of them have worked together hosting the Golden Globes three times and starring together in Mean Girls and Baby Mama. The two are set to work together once again in an upcoming comedy called The Nest.

  6. Chris Farley and David Spade
    This is one of the older duos on the list, and the two – due to Farley’s tragic passing—haven’t worked together for years. But in their prime as a duo, the two had us rolling with their performances on SNL, and in films like Black Sheep and Tommy Boy.

  7. Keegan Michael Key and Jordan Peele
    These two met in the Chicago comedy scene and continued to perform together as cast members of MADtv. In early 2012, their sketch comedy show Key & Peele first aired on comedy central and was instantly well-received. So far, the show has had four seasons and continues to garner acclaim while the two of them continue to work on future projects together. Needless to say, we look forward to it.

  8. The Frat Pack
    This isn’t a comedy duo. It’s actually the nickname given to a group of successful comedy actors consisting of Ben Stiller, Jack Black, Owen Wilson, Luke Wilson, Vince Vaughn, Steve Carell, and Will Ferrell. There are other actors mentioned in conversations about these groups, but the seven mentioned here are considered the original chapter of the group. Since so many of these actors made our list, we thought it would be appropriate to recognize them. The entire group has never appeared in one film together (though they came pretty close in Anchorman), but they have kept us laughing in different pairs and groups since the late 90s