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Horrible Bosses (2011) Poster

Trivia

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To promote this film, Warner Bros. Pictures Canada set up a 12-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/worst boss story for the chance of winning passes to an advance screening of the film.
Jennifer Aniston wore a brown wig to make her character a brunette and more oversexed, a departure from her usual lighter roles.
When looking for a dangerous bar, Gregory claims there is an Applebee's 3 blocks away. Jason Sudeikis says 'those aren't the shit heads we need.' Sudeikis would later become the spokesman for Applebee's.
While director Seth Gordon encouraged most actors to improvise their lines in various scenes, Jennifer Aniston stated she did not need to because her lines were "beautifully choreographed".
Vince Vaughn, Owen Wilson, Matthew McConaughey, Dax Shepard, Ashton Kutcher, Paul Rudd, Philip Seymour Hoffman, Jeff Bridges, and Tom Cruise were all rumored for roles at some point. Kutcher was attached to play the role of Dale Arbus, while Cruise, Hoffman, and Bridges were approached by New Line for the role of Dave Harken
Dale (Charlie Day) mentions a funny movie that starred Danny Devito. Charlie Day stars in the TV show, "It's Always Sunny in Philadelphia" with him.
Naomi Watts and Sarah Jessica Parker were considered to play Julia.
The screenplay for this film was featured in the 2005 Blacklist; a list of the "most liked" unmade scripts of the year.
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While Stacy talks to Dr. Harris in the dental clinic, an "elevator music" version of Gnarls Barkley plays.
The glasses worn by Jennifer Aniston at the dental clinic are custom made Oakley Radar Path.
Warren Sapp and Michael Strahan both auditioned for roles.
Meghan Markle and Wendell Pierce play Daughter/Father on the tv series SUITS
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Frank Oz and Brett Ratner were both attached to direct at some point.
Anne Fletcher was the studio's first choice to direct.
Ron White's role as a police officer is presumably tongue-in-cheek. His stand-up comedy involves numerous stories of his run-ins with the law.
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Spoilers 

The trivia items below may give away important plot points.

Kurt is the only one out of the three main characters to come in contact with the three targeted bosses. Kurt works for Bobby Pellitt, has sexual intercourse 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 hit man 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 door-frame.

See also

Goofs | Crazy Credits | Quotes | Alternate Versions | Connections | Soundtracks

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