* BigLippedAlligatorMoment: 90% of [[BizarroEpisode Heavy's Reta]][[ChristmasEpisode rded Holiday]]. Special mention goes to the intermission.
* ColbertBump: If the comments of any video of an Music/ADayToRemember song are of anything to go by, Kitty's videos have pretty much introduced his viewers to them due to [[AuthorAppeal how frequently he used their songs.]]
* CrossesTheLineTwice: in ''Heavy Takes his Driving Test'' the driving course has someone crossing the street, who gets killed in some way by most of team Red. The one who crosses the line the most is the Spy who gets out of the car and walks up to stab him. Adding even ''more'' to that is what the guy says as he dies.
--> '''Man Crossing Road''': What about my kids...
** Another moment in ''Heavy's Retarded Holiday'' has Ellis bringing out a small container of ''viagra'' and saying [[VideoGame/DukeNukem "I've got balls of steel."]] before he swallows the whole container and [[VisualPun gets literal balls of steel]] [[GagPenis the size of]] ''[[GagPenis cannonballs]].'' Ellis even ''knocks'' some poor guy flying through the air by smacking his face with them, complete with [[AnvilOnHead anvil]] sounds!
* HarsherInHindsight: Jack Johnson in "Moments with Heavy" wishes for the Heavy and Scout to get cancer and die; at the time many audiences found it funny, but it lost its humor after Colin passed away from leukemia in 2015.
* HilariousInHindsight: In the ''Quest of the Ultimate Sandvich", Both BLU Heavy and Francis settle their final showdown in a bumper car match in a small enclosed space surrounded by BottomlessPits. The VideoGame/TeamFortress2 2014 Scream Fortress update introduces the new Special Delivery map that just happens to have an extra minigame where every player will play a chaotic bumper car minigame that forces the player to compete against each other and bump the other team's car into BottomlessPits.
* TearJerker:
** There's one in ''[=Heavy's=] Retarded Holiday'', where Heavy saw his friends got obliterated by the giant cat one by one.
** On January 25, 2015, Colin Wyckoff died at the age of 20 after a long battle with leukemia. It was especially saddening since it was out of the blue and unexpected, and not only his fanbase but the Gmod machinima community as a whole grieved over him.
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