[[caption-width-right:330:At least they warned us.]]
'''''Jack and Jill''''' is a 2011 comedy film starring Creator/AdamSandler. The film tells the story of Jack Sadelstein (Sandler), a successful advertising executive enjoying life with his career and family including his wife Erin (Katie Holmes). But when he learns that his annoying twin sister, Jill (also Sandler), is coming over for the Thanksgiving holidays, and when she decides to stay in town a bit longer, this results in getting Jack to get Creator/AlPacino to date her so he can get Jill out of town, to less than satisfying results.
Notable for winning the UsefulNotes/GoldenRaspberryAward of 2011 in ''all 10 categories'', being the first film to do so.
!!This film provides examples of:
* AllLoveIsUnrequited: Jill does ''not'' return Pacino's feelings.
* AsHimself: Al Pacino.
* AttractiveBentGender: Sandler tries to pull this off in playing Jill, but ends up making Jill look like his transvestite twin brother more than his twin sister.
* BehindTheBlack: There's a scene where Creator/NormMacDonald's character goes on a date with Jill. Because he finds Jill repulsive, he decides to hide in the bathroom. When Jill comes looking for him, she opens the stall door to find it empty and leaves... only for the camera to pan up and show [=MacDonald=] hanging from the overhead light.
* ContinuityNod: The hobo from ''Film/HappyGilmore'' makes an appearance.
* CoversAlwaysLie: Mexican promotion for the movie made a big emphasis on famous comedian Creator/EugenioDerbez appearing on the movie, when his role wasn't too big.
* GameShowAppearance: For some reason, Jill becomes a contestant on ''Series/ThePriceIsRight''... and gets knocked out by the Big Wheel.
* InformedAttribute: The Jill we're told about is a sweet, bighearted woman who loves seeing her brother succeed. The Jill we're ''shown'' is mean, manipulative, loud-mouthed and obnoxious.
** Perhaps intentional to show just good she is at manipulating people that she can delude them into thinking she has merits that aren't actually there.
* LeaningOnTheFourthWall: Debatable, but at the end of the film we see Creator/AlPacino act in the new Dunkin' Donuts commercial; after seeing his spot, he orders the film be burned and that no one ever sees it again. He might not have just been talking about the commercial...
* ProductPlacement: This ''is'' an Adam Sandler movie, after all. Justified, such as it is - Jack works as an ad executive.
* ScrewTheMoneyIHaveRules: [[spoiler: Jack disguises himself as Jill so Al Pacino can spend time with "her" and agree to appear in the commercial. Eventually, Jack [[MyGodWhatHaveIDone realizes he's gone too far]] and runs off, to which Al asks if she'll come back if he agrees to do the commercial, to which Jack replies "forget the commercial!" Of course, Al Pacino does end up doing the commercial after all... and then wants all copies destroyed.]]
* SpiritualSuccessor: To Adam Sandler's recurring ''Series/SaturdayNightLive'' skit "GAP Girls", which featured him in (far more convincing) drag.