* ContestedSequel: All of the games after the second one, especially 3D
* CrowningMomentOfFunny: The druid in the first game explaining to Simon how to spot demons:
-->'''Druid:''' The only true way to find if a creature is a demon is to plunge a silver dagger through its heart! If the creature dies, then it is a demon. If the creature lives, then its heart is pure, [[MortonsFork and so we sacrifice it.]]
-->'''Simon:''' I bet you find a lot of demons that way.
-->'''[[SarcasmBlind Druid]]:''' Never been wrong yet!
** When using the Look command (which normally makes Simon describe the object you use it on) on a pair of [[HotAmazon Hot Amazons]]:
--->'''Simon:''' [[EatingTheEyeCandy I'm looking! I'm looking!]]
* OlderThanTheyThink: The first adventure parodied and referenced Tolkien's ''Lord of the Rings'' long before Peter Jackson popularized it with his movie adaptation trilogy.
* WhatAnIdiot: In the endgame of the first game, [[spoiler: Simon uses [[BigBad Sordid's]] own magic wand to [[TakenForGranite turn Sordid into a statue]]. So far, so good. Then he throws the wand in the lava to destroy it, which will turn all Sordid's statue-fied victims back to normal. Yeah... didn't think that through, did you, Simon?]]