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* RealLifeRelative: In addition to the Cusack siblings in the main cast, their sister [[Creator/AnnCusack Ann]] plays a drunken woman who accosts Martin and Debi when they're at the restaurant, and their brother Bill also appears at the reunion.

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* RealLifeRelative: In addition to the Cusack siblings in the main cast, their sister [[Creator/AnnCusack Ann]] plays Amy, a drunken woman who accosts Martin and Debi when they're at the restaurant, and their brother Bill also appears at the reunion.

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* CreatorCameo: Writers D.V. [=DeVincentis=] and Steve Pink both cameo in the film, as Dan Koretsky (a classmate at the reunion whom Debbie greets with a kiss) and security guard Terry Rostand.



* ProductionPosse: This is not the first time John Cusack got his buddy Jeremy Piven and sister Joan Cusack cast in supporting roles.
* RealLifeRelative: In addition to the Cusack siblings in the main cast, their sister Ann plays a drunken woman who accosts Martin and Debi when they're at the restaurant, and their brother Bill also appears at the reunion.

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* ProductionPosse: This is not the first time John Cusack got his buddy Jeremy Piven Creator/JeremyPiven and sister Joan Cusack Creator/JoanCusack cast in supporting roles.
* RealLifeRelative: In addition to the Cusack siblings in the main cast, their sister Ann [[Creator/AnnCusack Ann]] plays a drunken woman who accosts Martin and Debi when they're at the restaurant, and their brother Bill also appears at the reunion.reunion.
** D.V. [=DeVincentis=]'s daughter Sarah also cameos as the nervous teenage girl Dr. Oatman is counseling when Martin calls to fire him.
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* CaliforniaDoubling: The city of Grosse Pointe didn't allow filming beyond aerial footage, so it was mostly done in Monrovia, California.


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* DevelopmentHell: The script was written in 1991, the year of Tom Jankiewicz's graduation reunion, and only five years later it started filming.


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* OneBookAuthor: This is the only credit from writer Tom Jankiewicz,[[https://web.archive.org/web/20130206115223/http://www.dailybulletin.com/davidallen/ci_22505971/upland-screenwriter-hit-bulls-eye-grosse-pointe but he had steady work as an uncredited script doctor]].
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* CastTheExpert: Benny the Jet, a legendary kickboxer as well as Cusack's personal trainer, has a role as an assassin (his character is also Basque, which ancestry Benny has as well).

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* CastTheExpert: Benny the Jet, "The Jet" Urquidez, a legendary kickboxer as well as Cusack's personal trainer, has a role as an assassin (his character is also Basque, which ancestry Benny has as well).

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* CastTheExpert: Benny the Jet, a legendary kickboxer as well as Cusak's personal trainer, has a role as an assassin (his character is also Basque, which ancestry Benny has as well).

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* CastTheExpert: Benny the Jet, a legendary kickboxer as well as Cusak's Cusack's personal trainer, has a role as an assassin (his character is also Basque, which ancestry Benny has as well).


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* ThrowItIn: One of the reasons for the quirkiness and enduring appeal of the film is that it was built with this. Director George Armitage said that each scene was shot three times: once with the actors saying the lines as written, once with them being given the freedom to play around with them a bit, and once with them being free to say whatever they wanted, as long as they hit the story beats. In nearly every case, he went with the take that had the most improvisation. Minnie Driver in particular is visibly enjoying herself in this movie.
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* RealLifeRelative: In addition to the Cusack siblings in the main cast, their sister Ann plays a drunken woman who accosts Martin and Debi when they're at the restaurant, and their brother Bill also appears at the reunion.
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The hitman's name is Felix, not Benny.


* TheDanza: Basque kickboxer Benny playing Basque hitman Benny.
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* ProductionPosse: This is not the first time John Cusack got his buddy Jeremy Piven and sister Joan Cusack cast in supporting roles.

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* ProductionPosse: This is not the first time John Cusack got his buddy Jeremy Piven and sister Joan Cusack cast in supporting roles.roles.
* WhatMightHaveBeen: The original script does not have Martin and Debbie reuniting at the end, as foreshadowed by Debbie's line that he doesn't get to have her.
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* ProductionPosse: This is not the first time John Cusack got his buddy Creator/JeremyPiven and sister Joan Cusack cast in supporting roles.

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* ProductionPosse: This is not the first time John Cusack got his buddy Creator/JeremyPiven Jeremy Piven and sister Joan Cusack cast in supporting roles.
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* PopStarComposer: [[Music/TheClash Joe Strummer]]. Huh.

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* PopStarComposer: [[Music/TheClash Joe Strummer]]. Huh.Huh.
* ProductionPosse: This is not the first time John Cusack got his buddy Creator/JeremyPiven and sister Joan Cusack cast in supporting roles.
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* TheDanza: Basque kickboxer Benny playing Basque hitman Benny.
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Hey Its That Guy and Hey Its That Voice examples are being cut per TRS.


* HeyItsThatGuy: Car salesman/poet Bob Destepello is [[Series/TheWalkingDead Abraham Ford!]]
** Creator/HankAzaria and [[Series/BuffyTheVampireSlayer Mr. Trick]] are the two NSA agents.



* PopStarComposer: [[Music/TheClash Joe Strummer]]. Huh.

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* PopStarComposer: [[Music/TheClash Joe Strummer]]. Huh.
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** Creator/HankAzaria and [[Series/BuffyTheVampireSlayer Mr. Trick]] are the two NSA agents.
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* PopStarComposer: [[Music/TheClash Joe Strummer]]. Huh.
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* HayItsThatGuy: Car salesman/poet Bob Destepello is [[Series/TheWalkingDead Abraham Ford!]]

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* HayItsThatGuy: HeyItsThatGuy: Car salesman/poet Bob Destepello is [[Series/TheWalkingDead Abraham Ford!]]
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* HayItsThatGuy: Car salesman/poet Bob Destepello is [[Series/TheWalkingDead Abraham Ford!]]
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None

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* CastTheExpert: Benny the Jet, a legendary kickboxer as well as Cusak's personal trainer, has a role as an assassin (his character is also Basque, which ancestry Benny has as well).
* FakeAmerican: Brit Minnie Driver as Cusack's old love interest, from his hometown in Michigan.
* IncestuousCasting: Played with. Joan Cusack's character seems to be harboring a crush on Martin. (Martin doesn't reciprocate, he's too hung up on Debbie.) The Cusacks have something of a history of this trope.

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