* CrossesTheLineTwice: His stage persona is deliberately played up to be a terrible, narcissistic person who sings about things like Helen Keller being the perfect woman, falling in love with an [[LikesOlderWomen old woman]] and then her three-year-old granddaughter, giving head to Satan, a [[ThoseWackyNazis young boy named Adolf]] with all of the mannerisms of UsefulNotes/AdolfHitler, and a barbeque hosted by the Ku Klux Klan. [[RuleOfFunny But it's okay, because it's hilarious.]]
** And satirical.
* DudeNotFunny: [[https://twitter.com/boburnham/status/485603617538183168 After making a tweet making fun of people named Hunter]], Bo saw that there were a large number of people that got offended. [[CrowningMomentOfHeartwarming He then expressed sincere apology and regret and even started personally tweeting Hunters with apologies.]]
** The reason he doesn't do "Klan Cookout" or "Perfect Woman" live anymore. He's said that he worries about the latter being used to make fun of a real-life deaf girl.
* GeniusBonus: "What's domain, domain range? / A kid with too much in his pants". In math, domain is expressed by ''x'', while range is expressed by ''y''--[[DontExplainTheJoke the joke here being]] that said person is "XXY", which is the chromosomal makeup for a hermaphrodite.
* GrowingTheBeard: Seems to have happened around the time of ''Words Words Words.'' He's expressed embarrassment and dislike of much of his work prior to that period, which was more based around shock value for the sake of shock value rather than making a satirical point.
* HilariousInHindsight: In Welcome to Website/YouTube, he says that "most of the best [=YouTubers=] are either Asian or they're gay, so there's an untapped [=YouTube=] celebrity and his name is Creator/GeorgeTakei." While he's not so much specifically a [=YouTube=] celebrity, but since the song's debut, Takei has gained a huge internet following.
* {{Squick}}: The last few lines of "Sunday School":
-->I'm gay for Jesus\\
Fill me with Your grace\\
Pour Your love all over me\\
But please aim away from my face
* WhatDoYouMeanItWasntMadeOnDrugs: The music video for "Words, Words, Words". '''''Boy howdy.'''''
** SpecialEffectFailure: Very clearly invoked.