History YMMV / DieHardWithAVengeance

* CompleteMonster: Simon zigzags this. He's willing to murder who knows how many people using bombs, including a bomb on a subway train traveling under a heavily trafficked street in New York City... but he's ''not'' willing to [[WouldntHurtAChild put a bomb in a school]].

* HilariousInHindsight: The cops being able to track Simon Gruber down from [[spoiler:the bottle of pills he hands [=McClane=] out of pity]] seems like a hideously convenient plot contrivance, given the technology of 1995…but then again, [[https://nypost.com/2022/12/29/andrew-tate-brother-arrested-on-sex-trafficking-allegations-report/amp/ internet personality Andrew Tate got arrested]] in 2022 after Romanian police confirmed his location from a pizza box in a video he filmed as a Twitter clapback.

* AluminumChristmasTrees: The cops being able to track Simon Gruber down from [[spoiler:the bottle of pills he hands [=McClane=] out of pity]] seems like a hideously convenient plot contrivance…but then again, [[https://nypost.com/2022/12/29/andrew-tate-brother-arrested-on-sex-trafficking-allegations-report/amp/ Andrew Tate got arrested]] after Romanian police confirmed his location from a pizza box in a video he filmed as a Twitter clapback. Also counts as HilariousInHindsight.

* FranchiseOriginalSin: The first ''Die Hard'' film whose plot wasn't DieHardOnAnX. It worked here because Creator/JohnMcTiernan shot great action scenes and Creator/BruceWillis and Creator/SamuelLJackson had great buddy chemistry, even as the story and action felt less intimate and more spectacle-driven. The sequels after tried to replicate its {{buddy cop|Show}} formula, to swiftly diminishing returns.

** One of the cops makes an offhand reference to the 1993 World Trade Center bombing, saying how inconvenient it was. Ouch. The entire plot can be harder to watch after 9/11: a beautiful late summer day, terrorists making an attack on New York City, school children possibly being in danger...

* MagnificentBastard: [[NobleDemon Simon Gruber]] is a [[FromCamouflageToCriminal former soldier]], Hans' older brother and master thief just like his sibling. Distracting the New York City police department with bomb threats, Simon strings along John [=McClane=] and Zeus Carver to play games following his instructions lest he detonate his bombs. [[KansasCityShuffle Pretending to be masterminding revenge]] for his brother, Simon mobilizes on his real goal: robbing the Federal Reserve for over one hundred billion dollars in gold bars, while the preoccupied police force leave it nearly completely unguarded for Simon and his men to plunder. When [=McClane=] attempts to follow his men, Simon improvises with a discarded bomb to flood the tunnel [=McClane=] is in, nearly drowning him. Alleging to destroy the gold to disrupt the American power-grasp on the world, Simon really means to make off with it himself. Every bit as adaptive and [[AffablyEvil charming]] as Hans, Simon is yet another Gruber who is shown to be a brilliant criminal.
* OneSceneWonder: The Federal Reserve guard who tries to hold off Simon's gang with a shotgun, and Jerry, the surprisingly well educated truck driver, who solves the "what is 21 out of 42" riddle for [=McClane=] almost offhandedly.

* HilariousInHindsight:
** Meta example: The film's distributors, 20th Century Fox (domestic releases) and Disney (international releases) would cross paths again 22 years later in Disney's 2017 buyout of Fox.
** [=McClane=] calls Targo [[Series/TheAddamsFamily "Lurch"]]. The scene immediately cuts to bomb expert Charlie Weiss (Kevin Chamberlin), who, years later, was cast as Uncle Fester, in ''Theatre/TheAddamsFamily'', on Broadway.

** The fact that the actor who portrayed him passed away from cancer a year after the film was released makes this worse.

* MagnificentBastard: [[NobleDemon Simon Gruber]] is a [[FromCamouflageToCriminal former soldier]], Hans' older brother and master thief just like his sibling. Distracting the New York City police department with bomb threats, Simon strings along John [=McClane=] and Zeus Carver to play games following his instructions lest he detonate his bombs. [[KansasCityShuffle Pretending to be masterminding revenge]] for his brother, Simon mobilizes on his real goal: robbing the Federal Reserve for over one hundred billion dollars in gold bars, while the preoccupied police force leave it nearly completely unguarded for Simon and his men to plunder. When [=McClane=] attempts to follow his men, Simon improvises with a discarded bomb to flood the tunnel [=McClane=] is in, nearly drowning him. Alleging to destroy the gold to disrupt the American power-grasp on the world, Simon really means to make off with it himself. Every bit as adaptive and [[AffablyEvil charming]] as Hans, Simon is yet another Gruber who shows to be a brilliant criminal.

* UnintentionalPeriodPiece:
** The riddle referencing America having 42 presidents inevitably gets more and more outdated every four to eight years.
** The film is firmly dated to an era when cellphones weren't in mass circulation, as much of the plot could have been avoided had any of the main characters possessed one. Instead, they are forced to rush from phone booth to phone booth in order to prevent several bombs from going off. As of 2022, all phone booths in New York City have been removed, except for certain locations like prisons.