* ActorAllusion:
** In the fake trailers at the beginning of the movie, [[Film/IronMan Tony Stark]] and [[Film/SpiderManTrilogy Peter Parker]] as gay monks! Could also be an Actor Allusion to the relationship that Creator/RobertDowneyJr and Creator/TobeyMaguire's characters had in ''Film/WonderBoys''.
** "Dear Mr. Joe Quesada,[[note]]Editor-in-chief of Marvel Comics at the time the film was made[[/note]] boy do I have an idea for you..."
* AllStarCast: Creator/BenStiller, Creator/RobertDowneyJr, Creator/JackBlack, Creator/TomCruise, Creator/JayBaruchel, Creator/NickNolte, Creator/MatthewMcConaughey, Danny [=McBride=] and Creator/SteveCoogan.
* CowboyBebopAtHisComputer: Almost all coverage of the film refers to Creator/JackBlack's character as Jeff "Fats" Portnoy as if "Fats" is Portnoy's InSeriesNickname; Fats is actually the name of Portnoy's ''character''.
* DevelopmentHell: There were talks about developing a Creator/TomCruise-[=starring=] Les Grossman SpinOff circa 2010. Nothing has materialized since.
* DirectedByCastMember: Creator/BenStiller. Made filming the movie a little complicated since it's about filming a movie within a movie.
* DyeingForYourArt: Cruise's appearance as Grossman is completely transformed from sleek, muscular hunk to portly, hair, balding and scraggly. Grossman's personality and character, however, are typical Cruise.
* FakeAustralian: American Creator/RobertDowneyJr played an Australian who was playing an African American and even disguised himself as an Asian farmer. He's a dude playing a dude playing as a dude disguised as another dude. There's a reason he got an Oscar nomination for this role.
* FakeNationality: The Vietnamese cartel Flaming Dragon is led by a Chinese-American and the second-in-command is Filipino-American.
* TheOtherMarty: Owen Wilson was originally set to play Tugg Speedman's agent, Rick Peck, but after his suicide attempt, he understandably backed out of the role. The role ended up going to Creator/MatthewMcConaughey.
* StarringAStarAsAStar: Movie stars Creator/JackBlack, Creator/BenStiller, and Creator/RobertDowneyJr play fictional movie stars Jeff Portnoy, Tugg Speedman, and Kirk Lazarus (with Portnoy as more of a wacky fart-joke comedy guy, Speedman as a monosyllabic actioner, and Lazarus as an Oscar-obsessed intensive method actor.)
* ThrowItIn: A few scenes just happened on its own.
** The scene that had Tugg talking to a flying mantis it flying in his face actually happened by accident.
** When Tugg nearly fell into the river while he was crossing alone, Ben Stiller really did trip.
** The dance sequence at the end came from Creator/TomCruise randomly deciding to start hip-hop dancing during a make-up test. The crew thought it was funny enough that they worked it into the script.
** Some improvisation was used for the real film's dialogue -- in fact, Kirk was written as ''Irish'', but Creator/RobertDowneyJr found it easier to improvise with an Australian accent.
* UnintentionalPeriodPiece: Peck's obsession with [=TiVo=], a technology that has all but disappeared in the face of DVR and streaming services.
* WhatCouldHaveBeen:
** Peck was supposed to be played by Owen Wilson but he dropped out to seek treatment after a suicide attempt. Creator/BenStiller and Creator/TomCruise were also considered for the role of Peck.
** Creator/KeanuReeves was originally supposed to play Tugg, poking fun at the criticisms of [[DullSurprise his own inability to emote]].
** The original draft of the movie was about a bunch of actors developing PTSD as a result of the pre-production boot camp necessary to make them into plausible soldiers for a war movie.
** W. Earl Brown was one of the first considerations for Portnoy, but he personally turned it down because he felt Creator/JackBlack fit the role better.
** Mos Def was offered the part of Alpa Chino, but turned it down. Creator/KevinHart was also considered.
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