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1* CrossesTheLineTwice: And then some.
2** With his [[https://youtu.be/8ZXg0PHTWfo Live at the Del Ray performance]] of "Baby", he asks "Is it wrong to hope for [[https://en.wikipedia.org/wiki/Sudden_infant_death_syndrome SIDS]]?" The audience groans, and he takes offense by replying "Fuck you, it's ''my'' fuckin' baby!"
3** The premise of ''Little Tiny Mustache,'' in which a Jewish man's girlfreind turns out to be a neo-nazi.
4* HarsherInHindsight: The joke of "Little Tiny Mustache" is based around the absurd notion that dating someone who turned out to be a neo-Nazi was a one-in-a-million chance. With the resurgence of white nationalism in the late 2010s, finding out late in the game that your partner is a literal Nazi no longer feels so absurd.
5* SugarWiki/HeReallyCanAct: He got huge praise for his portrayal of Robbie Hart in the Broadway adaptation of ''Theatre/TheWeddingSinger''.
6* SugarWiki/HeartwarmingMoments: "Creator/JimHenson's Dead," a reasonably effective tribute to Henson with next to no swearing or LyricalDissonance. It's the closest he's come to writing a completely serious song.
7* HilariousInHindsight: The "[[UsefulNotes/BarackObama Obama]] Doesn't Stand A Chance" line from "Beelz". It has since been changed to "I'm the reason that Barack Obama's shitting in his pants."
8* NightmareFuel
9** "Priest," if taken at face value, is a surprisingly unnerving song about a man having a crisis of conscious as he comes to terms with his pedophilia, something he's completely ashamed of.
10** "Halloween" as well, though it's just audacious enough to not find genuinely frightening.
11* SuspiciouslySimilarSong: "Superhero" follows a similar chord progression for the ''Series/SesameStreet'' song "[[https://www.youtube.com/watch?v=kIq8jLj5TzU I Don't Want To Live On The Moon]]." Of course, [[InvokedTrope this was probably intentional]].
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