To promote this film, Warner Brothers Pictures Canada set up a twelve-foot Voodoo doll resembling a corporate boss in downtown Montreal. People were given the chance to vent their office frustrations on the doll by stabbing and hitting it with large needles. They were also encouraged to share their best or worst boss story for the chance of winning passes to an advance screening of the film.
While Director Seth Gordon encouraged most actors and actresses to improvise their lines in various scenes, Jennifer Aniston stated she did not need to because her lines were "beautifully choreographed".
When looking for a dangerous bar, Gregory claims there is an Applebee's three blocks away. Jason Sudeikis says "those aren't the shitheads we need." Sudeikis would later become the spokesman for Applebee's.
Colin Farrell was heavily involved in the look of his character- the comb over and prosthetic stomach were his idea. He also decided his character would have an obsession with Chinese dragons, and took part in developing the design for Bobby's apartment.
The trivia items below may give away important plot points.
Kurt is the only one of the three main characters to come in contact with the three targeted bosses. Kurt works for Bobby Pellitt, has sex with Dr. Julia Harris (Kurt is never seen interacting with her, just Julia opening her front door to invite Kurt into her home for sex) and is held at gunpoint, along with Nick and Dale, by Dave Harken. Nick works for Harken, he never interacts with Pellitt (though he does witness Harken murdering Pellitt), and is never seen with Julia. Dale works for Julia, is held at gunpoint by Harken, but never interacts with Pellitt. Additionally, he has interactions with Harken when Harken gets angry with him for littering, after which Dale saves his life (he didn't know it was Harken) when he almost dies because of a peanut allergy.
At the seedy motel, where the supposed hitman is being interviewed. When he shows up at the door, a mezuzah (a small Jewish religious case containing a prayer scroll found on the door posts of Jewish homes) is clearly seen on the doorframe. This is also true for the bathroom Bobby walks out of in his first scene.