* {{Anvilicious}}:
** "Michael Jackson is Dead" is a scathing and unsubtle rant at both the media and general public's hypocrisy toward Michael Jackson, demonizing him while he was alive and canonizing him after he died.
** Similarly, "Song for Miley" calls out the general public and the media for their hypocritical outrage about Miley Cyrus VMA twerking while being totally fine with several other celebrities doing the same thing in music videos.
** From "WTF Collective 2", there is "MC Homophobic Fucking Asshole" named that way just in case it wasn't clear homophobia is bad.
* CrossesTheLineTwice: Actually, he crosses it much more often than that.
** Two sketches that sum up his brand of sick humor as much as anything else: [[https://www.youtube.com/watch?v=EVcyNANK5cY "Rapist Glasses"]] and the sequel, [[https://www.youtube.com/watch?v=15S0g8pG6HU "Pedophile Beards."]]
** [[https://www.youtube.com/watch?v=sfWwUR6kiCs Tennis Ball]] is a great example of crossing the line twice.
* EnsembleDarkhorse: Steve. ''"[[CatchPhrase You want some of this, bitch]]?!"''
* FridgeBrilliance: MC Final Verse says in WTF Collective 2, "One was enough, we didn't need a sequel Jon. Make a fourth Show Me Your Genitals or another Normal Guy." After Chorus Guy's suicide, who shows up but MC Vagina. In addition the first rapper in WTF Collective 3? MC Normal Guy.
** "A New Beginning", a song he released under his alternate branding of ''Wolfie's Just Fine'' (which focuses more on serious music, than comedy), is about watching ''Film/FridayThe13thPartVANewBeginning'' at a young impressionable age. However, the chorus includes the line "Here comes Jason" repeated over and over, despite the fact that ''A New Beginning'' is actually about a copycat killer named Roy Burns, and not Jason Voorhees. That is, until you remember that Jon is watching this as a child, and is clearly too busy being traumatized by the violence to actually pay attention to the story, it would make sense that he would have it burned into his head that the villain is Jason, considering Jason was massively popular in the '80s, even to people who hadn't seen the movies.
* SugarWiki/FunnyMoments: "Pop Song", and everything M.C. Vagina says.
** In "Fuck Everything":
-->''And fuck coasts I don't give a fuck 'bout where water meets land''\\
''And fuck boats just cause you float you think you so fuckin' bad?''
-->''And fuck jokes I don't need to be funny all the time''
-->''[[BlackComedy My dog has a tumor and he's probably gonna die.]]''
* HarsherInHindsight: In "Everyday Normal Crew", Jon notes that Steve will "probably have a heart attack sometime soon." Nino, the actor who played Steve, passed away in 2014.
* HoYay: Taken to a ridiculous extreme in [[https://www.youtube.com/watch?v=x0zBI-wwjsg this sketch.]]
* {{Squick}}: Taken to hilarious extremes in [[https://www.youtube.com/watch?v=BnIX8544IoI Birthday Song]], which tells you everything you never wanted to know about [[spoiler:how you came into existence.]]
** Possibly worse than that is "In Different Ways," an R&B ballad about [[spoiler:penile dismemberment.]]
*** Even worse is the chorus to the [[CringeComedy "2 Girls 1 Cup song"]]
* SugarWiki/VisualEffectsOfAwesome: "Pop Song." Lajoie plays every member of the band, and it's actually quite hard to tell. Even the editing is genuinely high-quality.
* TheWoobie: [[HeroicSelfDeprecation MC Insecure]], [[RapeAsDrama MC Amnesia]], [[DrivenToSuicide Chorus Guy]], [[ArmoredClosetGay MC Knows Too Many Facts About Bees]], and the dancer from "I Can Dance" [[spoiler:who was molested as a child]].
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