When I think of what was controversial in the 1950s, I think of Elvis being filmed from the waist up. So, I went into Lolita thinking it couldn’t possibly be as scandalous as advertised nearly six decades later.

Wrong. Lolita makes To Catch a Predator seem like child’s play (so to speak). As oddly hilarious as it is disturbing, Nabakov’s classic is one of the most insightful accounts of pathology (what many refer to as Humbert’s unreliability) I’ve ever encountered, and still has the power to make the most hardened reader (i.e. me) queasy.

Reading this through the lens of a literary representation of mental illness, it’s easy to see Humbert’s source for pedophilia — his stunted sexuality from an age-appropriate childhood romance left unconsummated and forever associated with death and loss (and run-on sentences).

More subtle, though, is Humbert’s troubled conscience, which vacillates between self-awareness and self-fulfillment. Through carefully dropped hints, we realize that he is aware of Dolores’ vulnerability and her lack of interest in their adult activities. He knows what he’s doing is damaging the poor girl, but more often than not, his needs hijack his decisions.

The consequences fall squarely on the not-so-frail shoulders of 12-year-old Dolores Haze, who endures his abuse into her teen years. (Side note: Through Lolita, Nabokov paints a clear portrait of borderline personality disorder, which makes her story even more tragic.)

Still, through Humbert’s rationalizations, however twisted or self-serving, he does try to protect his stepdaughter in his own clumsy way. While his selfishness trumps all, his moments of lucid affection make him as close to sympathetic as can be (sympathetic enough that we’re rooting for him in his showdown with creepy Quilty).

What a tremendous book, and perhaps the greatest work of transgressive fiction. Nabakov’s play with language is remarkable (especially considering English was his second tongue), and the pain and desperation sweating through the pages of this novel make it timeless.

Troubling, complicated and a work of genius, this is an unsettling read for the ages.