!!For the movie:

* BigLippedAlligatorMoment: The naked woman who pops up on John Spartan's video screen in his apartment. He's just as confused, too. The novelization indicates the purpose of the scene is to demonstrate to him that video-calling is the norm in the future.
* CompleteMonster: [[AxCrazy Simon Phoenix]] hails from a {{dystopia}}n era of Los Angeles when the city was being overrun with violent criminals in the late 20th century, where he indulged in theft, kidnapping, rape, arson, and murder to his heart's content. He starts the movie by holding 30 people hostage and demanding a ransom, when in fact he already killed them all for his perverse amusement before the cops even arrived. He manipulates the CowboyCop John Spartan into making a misjudgment that makes him seem responsible for their deaths in the raid on Simon's compound, sending them both to a [[HumanPopsicle cryo-prison]] for decades. He's woken up in 2032, when the rebuilt megacity of San Angeles has been turned into a crimeless nanny state after a great calamity. Simon indulges in his freedom to be a maniac and spread chaos again, casually murdering almost everyone who gets in his way by beating people to death, [[EyeScream gouging out someone's eye]] to [[BorrowedBiometricBypass bypass a retinal scan]], hacking into a computer to [[ImpaledWithExtremePrejudice impale someone to a wall]], or simply shooting them. He was unfrozen by the new society's [[WellIntentionedExtremist benevolent dictator]] Dr. Raymond Cocteau to assassinate Edgar Friendly, the major rebel leader trying to undo the oppressive system. Simon sets out on this task with murderous glee, killing many innocent bystanders in the process. He teams up with his old gang after they're unfrozen and eventually [[TheStarscream murders Cocteau]] to [[DystopiaJustifiesTheMeans start a new lawless dystopia]] where he and his minions can commit crimes all day. He starts by unfreezing every criminal locked up in the cryo-prison, including murderers, rapists, and serial killers, and gunning down all the technicians because [[YouHaveOutlivedYourUsefulness he no longer has any use for them]]. Phoenix is one of the poster boys for the malicious type of ChaoticEvil villain, inherently hating rules simply because they hold him back from being a murderous psycho.
* CultClassic: At the time of its release the film wasn't a box office hit and got mixed reviews. But these days it comes across as an AffectionateParody of action films from TheEighties and [[TheNineties Nineties]]. There's a good amount of LampshadeHanging, a mix of {{Deconstruction}} and {{Reconstruction}} about John Spartan's CowboyCop image, and most of the satire, whether about PoliticalCorrectnessGoneMad and unhealthy things being illegal or iconoclasts actively chafing at rules just for existing and deliberately living in grungy filth, has, if anything, actually gotten ''sharper''.
%%* EvilIsCool: What do you expect from Wesley Snipes as the BigBad Simon Phoenix.
* FoeYay: Phoenix to Spartan in 1996. When they both got arrested he implied he planned on [[PrisonRape raping him in prison.]]
--> '''Simon Phoenix:''' We're gonna spend a lot of quality time together. See you [[TermsOfEndangerment sweetie, honey, SUGAR!]]
* FunnyAneurysmMoment:
** Looking through the Cryo-Prison inmate list, Phoenix exclaims "Jeffrey Dahmer? I ''love'' that guy!" In 1994, Dahmer was bludgeoned to death in prison; the line was subsequently cut from a number of broadcasts.
** The name "Scott Peterson" comes up during Huxley's access of the parole hearings. Presumably, this is not [[https://en.wikipedia.org/wiki/Scott_Peterson the man who]] kidnapped and murdered his pregnant wife in 2003.
** Spartan crashes the 1970 442 through the floor of an Oldsmobile dealership in 2032. Oldsmobile was discontinued by GM in 2004.
* HamAndCheese: Wesley Snipes gleefully chewing the scenery as Simon Phoenix.
* HilariousInHindsight:
** Creator/ArnoldSchwarzenegger is briefly mentioned as a former President, with Huxley explaining that his popularity forced an amendment to the Constitution to allow him to run. Now, Schwarzenegger is a former governor of California, and there is a serious and fairly popular movement to amend the Constitution to allow naturalized citizens to become president.
** Gamers may find it difficult to hear the name John Spartan, Prisoner 117 without thinking of John-117 the SPARTAN-II SuperSoldier of ''VideoGame/{{Halo}}''.
** In 2015, the supposed year of the Franchise Wars, Taco Bell's parent company reported a generous upturn in earnings, while [=McDonalds=] and Burger King started to go into a slight decline.
* TastesLikeDiabetes: San Angeles in the year 2032 is squeaky-clean to the point of absurdity, with commercial jingles from TheFifties as the most popular genre of music and everyone relentlessly cheerful at all times. Your almost cheering Phoenix on, at least at first, if for no other reason than you want to see some chaos inflicted on this smiley, chipper city.
* SpecialEffectsFailure:
** When the future cop car was jumping through the SAPD sign, the letters and symbols were each engraved on a separate plate of glass. Just before the car hits it, all but one of the plates are pre-broken; the unbroken one has a broken one on the other side of it, making it obvious it wasn't the car that did it.
** While it's more Makeup Failure, but [[IncrediblyLamePun keep an eye]] on Phoenix's Heterochromia. Several times in the film his blue and brown eye noticeably switch sides between shots.
** When Simon's hideout is blown up at the beginning, you can clearly hear people in the background cheering at this extraordinary demolition. [[note]]While in-universe, it could be other criminals cheering at the destruction, in real life, it's probably the noise of onlookers or crew; they actually destroyed a real building for that shot, an old Power & Water in Los Angeles that was in fact scheduled for demolition at any rate[[/note]]
* WhatAnIdiot:
** The museum's [=20th=] century weapons exhibit has functional and ''loaded'' weapons on display with relatively light security. Even discounting Simon Phoenix as an OutsideContextVillain for the setting, Edgar Friendly could have done a lot of damage if he'd ever decided to do a smash-and-grab on them.
** Cocteau feels comfortable freeing Phoenix because Phoenix' conditioning prevents Phoenix from killing Cocteau... but Cocteau never considered that Phoenix could order someone ''else'' to kill him.
* WhatDoYouMeanItsNotPolitical: Some have described ''Demolition Man'' as being one of the most libertarian movies ever made. One of the film's villains is a scientist who has basically created the ultimate nanny-state, where everything deemed bad for you has been outlawed. And Edgar Friendly and his followers, who are initially portrayed as terrorists, turn out to be sympathetic freedom fighters who want to make their own decisions without the overbearing government's influence.
!!For the pinball:

* ComplacentGamingSyndrome: Some players will always select the "Freeze" award on the Cryo-Claw -- it provides progress towards multiballs.
* SoBadItsGood: The [[https://www.youtube.com/watch?v=bgG8wQ3Msqw promotional video]] for the [[Pinball/DemolitionMan pinball,]] which attempts to duplicate the atmosphere and special effects of the movie on a shoestring budget, while hyping up the game's gun grip controllers, all intermixed with actual film clips. It fails spectacularly, but has an innocent appeal, like watching an eight-year-old attempt to duplicate a Creator/MichaelBay film in his backyard.