* CaliforniaDoubling: The city of Grosse Pointe didn't allow filming beyond aerial footage, so it was mostly done in Monrovia, California.
* CastTheExpert: Benny "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).
* 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.
* DevelopmentHell: The script was written in 1991, the year of Tom Jankiewicz's graduation reunion, and only five years later it started filming.
* 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.
* 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]].
* PopStarComposer: [[Music/TheClash Joe Strummer]]. Huh.
* ProductionPosse: This is not the first time John Cusack got his buddy Creator/JeremyPiven and sister Creator/JoanCusack cast in supporting roles.
* 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.
** D.V. [=DeVincentis=]'s daughter Sarah also cameos as the nervous teenage girl Dr. Oatman is counseling when Martin calls to fire him.
* 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.
* 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.