I'll give him this: Tucker entertains. His stories are for the most part well written, and his third book is a fun and easy, albeit frivolous read. As usual, a good chunk of the book is just emails to and from his friends, some dating back years. That, coupled with multiple pages dedicated to his "sexting" with his core fan base, i.e. immature and insecure teenage girls, sort of undermines his claim of being a prolific writer.
Tucker is at his best when he writes about his friends' various idiosyncrasies. The chapter about his friend Hate was by far the funniest, containing some exemplary wit.
He is absolutely at his worst when he gives life advice. The "wisdom" he imparts is shallow, hackneyed, and hardly conducive to forming good character. At one point in the book, he suggests that kids shouldn't listen to anything their parents say, that they should just follow their own rules and the hell with the norm. So, when your dad preaches the importance of virtues such as loyalty, honor, fortitude, and honesty, just ignore the old man. Very rebellious, Tucker! This is painfully cliched and unenlightened advice.
By far the most disturbing chapter is on Miss Vermont.
It reveals a vindictive, pathologically narcissistic, and petty side of Tucker. He takes extreme pride in destroying a young, innocent girl for absolutely no good reason. He comes off as border-line sadistic in challenging Miss Vermont to write her version of events. Miss Vermont didn't want stories about her private sexual encounters published on the internet (who would?), yet Tucker takes delight in revealing intimate details about their relationship. Worse, he hides under the first amendment to justify his actions. Tucker fancies himself as a champion of free speech, when the real story is Tucker's cowardice in continuing to taunt a girl, whose privacy he had already shamelessly violated. Tucker feigns indignation at Miss Vermont's hypocrisy--her preaching chastity on the one hand, and not living up to it on the other. And that is apparently good enough reason for Tucker to go after her with a religious like fervor. He almost exudes moral righteousness that comes off as incredibly petty, creepy and vengeful. In short, the Miss Vermont story makes him look really small, vindictive and cowardly.
Hilarity Ensues is a fun read--with the salient exception of the Miss Vermont chapter--but it belies Tucker's delusion that he has grown or that he is an exceptional writer. He is still petty, at times bitter, and never particularly insightful.