* FanonDiscontinuity: Many fans prefer to ignore ''Life Is Rough When You Lose Your Stuff!'' and imagine that ''You Are What You Eat From Your Head To Your Feet'' was the final adventure game in the series, due to the former coming out after Humongous was bought out by Infogrames, and thus lacking a lot of the talent that worked on the earlier games in the series.
* GoodBadBugs:
** ''Life Is Rough When You Lose Your Stuff!'' has two [[MutuallyExclusivePowerups mutually exclusive ones]], both involving the Dresser Scaling mini-game.
*** If you don't want to scale the dresser, just have Sam fall down the first time you play the mini-game. From then on, Sam will be able to skip straight to the top of the dresser as if you had already completed the mini-game.
*** If you have completed the mini-game and can play it from the menu, playing it from there and having Sam fall down will warp Sam to the bottom of the dresser, regardless of where he was when you accessed the menu. This basically serves as a WarpWhistle (especially useful in a game with LoadsAndLoadsOfLoading), and even a DoorToBefore since it still works after the PointOfNoReturn near the end of the game (allowing Sam to go back and pick up any [[CollectionSidequest trading cards]] he may have missed).
** If you use Debug Mode to warp to the door from the mine to Darkness' house, and you've neither unlocked the door nor oiled King's wheels, [[VocalDissonance Sam will speak in King's adult voice when you click on the door]].
* HilariousInHindsight: In the first game, Pajama Sam meets a boat named Otto. A few years later, Sam's voice actress, Pamela Segall Adlon, would go on to voice a character named...[[WesternAnimation/TimeSquad Otto.]]
** The vortex-like transition to the Land of Darkness in the first game looks very similar to how ''VideoGame/NightmareNed'' began.
* {{Moe}}: Many of the characters in the games can be seen as quite huggable, but Pajama Sam himself takes the cake. Being a superhero fanatic certainly helps.
* SugarWiki/MomentOfAwesome: Towards the end of the second game:
-->'''Lightning''': And this is the volume control for the "ka-booms"!\\
'''Sam''': Oh boy! (Turns it up all the way)\\
'''[[WrittenSoundEffect KA-BOOM!]]'''
* NightmareFuel: [[NightmareFuel/PajamaSam Has its own page]]
* PeripheryDemographic: The games are primarily aimed at children, but there's quite a few adult fans as well, especially those who grew up playing the games.
* TheyChangedItNowItSucks: The fourth game changed Sam's voice from Pamela Adlon to Elisha Ferguson. Ferguson's take on Sam is widely regarded as being inferior to Adlon's.