When Jack Hastings goes to Gary Zimmer with his decision to run for mayor, Steve Carrell gets spooked being suddenly woken up to Chris Cooper watching him sleep and breaks one of the pieces to the headboard. Camera cuts from Cooper to Carrell, the headboard is now fixed.
In the bar scene early in the film, the coaster holders on the bar near Gary keep changing positions in between shots.
On the flight back to Wisconsin, the beer level in Jack's glass does not change despite him picking up the glass to drink, several times. Then when the level does actually decrease, in the next shot the level has increased.
All elections for mayor in Wisconsin are non-partisan.
Little Mike misquotes Neil Postman, "in entertaining ourselves, news has become entertainment." The quote given should have been noted as paraphrased or the correct quote, "TV serves us most usefully when presenting junk-entertainment; it serves us most ill when it co-opts serious modes of discourse; news, politics, science, education, commerce, religion."
Little Mike says that the title of Neil Postman's book is "Entertaining Ourselves," when, in actuality, it is "Amusing Ourselves to Death: Public Discourse in the Age of Show Business."
A bartender would not likely serve Gary an unopened beer bottle, this would allow the customer to exit the bar with the alcohol.
The black SUV at the gas station has no front license plate, which is a requirement in Wisconsin (where the car was rented).
The silly demographics the Hastings team is trying to court include "WoMAM"s, explained as "white middle-aged men", which does not contain a single "o"; even the on-screen expansion of the abbreviation just leaves it out. In the cast credits, the actors are listed under "WOMAMs" with an even odder capital "O". (If Steve Carell improvised the line, he might have meant WMAM, pronounced wuh-mam.) A related mistake is that the subsequent explanation of "YAWM" as "younger aged white men" is missing a corresponding hyphen.
Elections for mayor in Wisconsin are held in early April, so the weeks before the election would be in February and March, when Wisconsin winters are bitter cold. Yet an outdoor evening event shows everyone walking around in short-sleeves and other summer clothing.
After the music credits, the word "soundtrack" is misspelled as "soudtrack,"
leaving out the letter "n."
Gary is bother ed by Faith smoking in the bedroom in which he is staying, so he opens a window, but he leaves the drapes and curtains closed.
Jack pronounces Wisconsin "Wesconsin," with an "E" sound instead of an "i" sound.
The Hastings pamphlet Gary holds up to illustrate the birth control misjudgment says "stand up for woman's health"; it should be women's with an E.