‘Lolita,’ Jeffrey Epstein, and the Real Meaning of a Challenging Classic

Hey, y'all, we're going to do something a little different today on Old School. Instead of being the host, I'm going to be interviewed. Rafaela Sewert from the Free Press is going to talk to me about Vladimir Nabokov's novel, Lolita. Take it away, Rafaela. This book has deep relevance in the current moment. Recently, the Department of Justice released three million pages related to the Jeffrey Epstein case, and references to Lolita show up all over the files. There are references in emails. There are photographs with quotes from the book written in pen onto girls and women. He reportedly had one single book on his bedside table, Lolita. He also reportedly had a first edition copy. So clearly, he had an obsession with this book. At the same time, it has come up across pop culture from Lana Del Rey to Katy Perry to Lena Dunham. And, you know, the illicit relationship described is often glamorized in a way that I think would shock the author. So today I wanted to do a deep dive on Lolita about this novel, which is fundamentally about a homicidal pedophile rapist and how that has come to occupy such a prominent place in American culture. So to do that, obviously, I wanted to go to you, our literary expert. So let's start at the beginning. Where do we find the narrator and protagonist of this book, Humbert Humbert? Well, as the book starts, we find the narrator, Humbert Humbert, dead. The book is presented to us as a document that he wrote in prison. After he passed away, he gives it to somebody who gives it to a relative who's a kind of psychologist. And this man at the beginning, John Ray Jr. is his name, says, you know, this document was written by a man named Humbert Humbert who is in jail. This document details his relationship with this young girl, Lolita. So it's presented after both Lolita and Humbert are dead. At the very beginning of the novel, we see a kind of glimpse of him engaged as a 12 or 13-year-old boy with a young girl named Annabelle. And the novel presents his first sexual experience with this young girl, Annabelle. And what we learn is that she, at a very young age, dies. I think it's typhus. I can't quite remember what the—but she dies. and he is, you know, sort of taken aback by this or he's very much scarred by this as a young boy. And so the novel is presented to us as a kind of, with this frame that he's had this experience with a young girl during his boyhood. And he says he doesn't know whether what he's about to tell us is, came about, namely his relationship with Lolita, as a consequence of his being scarred by these early sexual experiences with this young girl who died. He says, I don't know if that's the psychosis from which I suffer or that's any cause here. He also says, it may be that it's inherent in me to have these problems. So he gives you a V in the road immediately. You can make sense of my relationship with Lolita, a 12-year-old girl, by way of something that happened to me in my childhood. Or you can say it's inherent and it's some psychological flaw with me. And he doesn't tell us really which one he thinks. And then we set off. So that's how the novel begins. And by twists and turns, Humbert comes to a town in which Lolita's mother, Charlotte, lives. And Charlotte's husband is dead. And Humbert wants to be a boarder at their home. And he goes to the home and he's like, man, this woman sucks. This town kind of sucks. And then he sees Lolita in a garden, and he's like, okay, she has a 12-year-old daughter. Don't mind if I do live here. And that's how the whole thing begins. And he, correct me if I'm wrong, he believes it's Annabelle Lee incarnate or, you know, some version of her passed on. Yeah, he seems to be chasing something like that. It's sort of mysterious to me whether he wants us to make that linkage as strongly as I think we're tempted to, especially today in kind of psychotherapeutic culture. We want to say, you know, things that happened to you in your childhood manifest themselves in your adulthood. The other, of course, fascinating fact about him is that his mother was struck by lightning. And so he himself was motherless. And so he begins psychotherapy as a very young child because his mother was struck by lightning. And so he says throughout the novel with Annabelle, as you just mentioned, with his own mother and with Lolita. I've had some issues with women, you know, for a long time. Throughout the book, there's this question about how to trust Humbert Humbert as the narrator. And the foreword is not by Humbert Humbert. It's by this other fictional character who is his lawyer's cousin, I believe. And, you know, one thing that is signaled is sort of a warning for the reader to be vigilant. In a way, do you think Nabokov is preparing the reader to be wary of the story that is about to be told? Can you just draw this out for us a little bit? Yeah, I think, you know, there's a lot of discussion in the scholarship about whether Humbert is trustworthy. And I do think that Nabokov plants the seeds at the beginning for you to wonder about this man. The reason I think that he does that and the way I think that he does that is that Humbert is honest about his own sickness. In other words, it's clear to you from the very beginning that the perspective from which this book will be told is the perspective of an insane person. And he talks about that he's been in the sanitarium a few times and that he's even put himself in the sanitarium a few times. And so this, I think, is Nabokov's way of saying, whatever this novel is going to be, reader, from the very beginning, know that the person's perspective from whom it emanates is not an ordinary or well human being at the very least. It's clear throughout reading it that Humbert Humbert is delusional, a little bit self-obsessed. That was my reading of him. And also there are moments where he seems to psychoanalyze himself and identifies obviously the onset of his pedophilia through this youthful relationship he has with Annabelle Lee, even though he's also a child at the time, but he identifies that he's attracted to what he describes as nymphets, women who are between the ages of 9 and 14. He refers to himself as a pervert, and there is some degree of self-awareness. And I think that brings up a question is, you know, does the book ask the reader to humanize this man, even though he's a predator, or think of him as just completely self-delusional? How do you understand Nabokov's intent here? Well, I think part of the genius of Nabokov as a writer, and this has been noted about the book now for over a half century, is that you do come to sympathize with Humbert in a very bizarre way. And I think for a reader, the genius of the writer is that he makes you feel uncomfortable because you start to see the point of view as sane. In other words, you know from the beginning Humbert Humbert is crazy, and yet there are times in the book when he describes his longing for Lolita in such terms as to make you almost think he's not crazy. And so I think Nabokov is interested in exploring, like any great artist, the full range of human psychic possibility. that is to say in all of its goodness and all of its evil. You can see this today in our fascination with true crime novels. People want that forbidden stuff. They want to see people bleed. They want to see people murder. They want to kind of get into the head of such a person. Well, Nabokov does that here with arguably that crime, which is the most severe, which is arguably even more than murder, which is pedophilia. And so I think that the genius of Nabokov is that sometimes he makes you despise, and you should despise, Humbert, but at other times you start to question yourself. And what that does is it makes you wonder about your own sanity. And so he begins to teach you in this way. This was something that stood out to me is that he is objectively monstrous, right? He's a narcissist. He's a murderer. He's a rapist. He's a pedophile. He manipulates everyone around him to get access to this 12-year-old child. And still, I think a lot of people read him as a compelling character. Why do you think it is that he reads as compelling as he does? You know, I wonder about that myself. I mean, some of this has to do with who he is. So let's just say basically who he is. He's sort of a tall, dark, and handsome type of man. So you get at the beginning, and he often, he has a kind of narcissism about him. He reflects on how handsome he is, and he reflects on the fact that he's irresistible to women. And now this is a kind of telltale sign. I suspect that something is very wrong with him. But that's fascinating. I mean, that he's kind of this standard type. The way Humbert Humbert speaks, he's very intelligent. He's a literary scholar. He's a sort of literature professor. And so he's well-read. He's sophisticated. He's constantly making literary references. In the Bokov's beautiful vocabulary, I mean, Humbert comes to life as this charismatic, well-spoken gentleman of a man who has this dark sin. And I think anytime you encounter a character like that, who's so far from the ordinary, who is charismatic at the same time that he's terrifying, it makes you sit up. And so I think that's part of what's compelling about him. he comes to the united states and he ends up living as a border in the house of charlotte he meets charlotte's daughter dolores hayes who he starts calling lolita and he marries the mother in order to get closer to dolores can you tell us about the other main character dolores hayes referred to as Lolita? Yeah, this is a very interesting question because, as we said earlier, the story is told entirely from Humbert's perspective. This means that the only access that we have to Dolores, or as I'll call her, given with the title of the book, Lolita, is through Humbert's eyes. So we already can't say that we have an accurate reflection of this young girl because we know the person from whom we're getting the information is a pedophilic psychopath. That said, what we do know about her is that she's 12 years old. It's that she's not very good in school. She doesn't have a very good relationship to her mother. She's not a very hygienic child. He talks about how she's often dirty. Later in the book, it comes to sight that she does have some interests. Her interests are in Hollywood starlets, in acting, in the theater, and in music She also like many young children kind of obsessed with objects Humbert begins to buy her gifts and she just loves this This is a way of manipulating her But for all intents and purposes, she comes to sight before her interactions with him as relatively normal, if somewhat disobedient. She's fatherless because her mother's husband was killed, which gives Humbert an entry point. But the other thing to say about her is throughout the novel, it becomes clear that she's suffering. She's a normal girl in the day, but at night she's often crying. And Humbert has to buy her affections and try to comfort her. And she's a child who over the course of the novel, her world becomes completely disoriented. She comes to find it normal to be traveling around the country with an older man, having sexual trips in hotel rooms, but being bought fabulous meals and toys. And so what you see in the novel is a gradual transformation of this young girl into a victim of a horrible crime. And it's interesting that that transformation occurs in the novel because it means that Humbert himself, who's telling us the story, sees it too. But that's in some who she is. Well, just to set up the listener, for those who haven't read it, basically the mother dies in a car crash and then Humbert Humbert, one might say kidnaps this child who is sort of his stepdaughter and then he takes her on this cross-country journey where he's basically serial raping her. I think that would be like the most accurate depiction. His depiction is that they're having like a love affair as they travel across the country, despite the fact that she's 12 and he is, I think, 38. He says she's seducing him and he's sort of projecting what seems like his interpretation of a sexual tension that doesn't actually exist. Yeah, I mean, he is the aggressor here. So we should be clear. It's, you know, there's this kind of way of reading the book that she's seducing him. That seems to me to be largely false, largely because of her age. You know, their first encounter comes in her home. And it's a terrifying, horrible scene in the book. It's one of the most famous where she puts her legs across his lap very innocently. Her mother is out of the house. And fully clothed, he, for lack of a better term, manages to get himself off underneath his clothing by the fact that her legs are on his lap and he sort of moves around in such a way. This is not her seduction. She's not seducing him at all. She's just being a very innocent child with a trusting adult. So at every moment, Humbert is the one in control. Now, it is true that at one point in the novel, she does sexually awaken. So as you described, her mother dies in the course of the novel. It's very interesting the way her mother dies. Humbert is found out. Her mother comes to see that the reason that Humbert is in her home is that Humbert is interested in her 12-year-old daughter. And her mother is horrified by this fact, even more horrified because Humbert has married Lolita's mother to get access to the young girl. I mean, imagine how horrible this is. And so her mother begins to write these letters exposing him. She picks up the letters. She takes the letters to the mailbox outside, and she's hit by a car. Humbert goes and gets the letters. No one knows that she's found out, and no one knows that he's really there for Lolita. And so he becomes, to answer your question, the initiator. Now, what ends up happening is that she tells him, look, I'm sexually awakened because when I was away at camp one summer, I engaged in sexual activity with another girl and then eventually with a young man. And so it's at that point that they're on the road together. Her mother is dead. He sort of kidnapped her, but everybody thinks that he's her father. So they've let her go with him. I know this is complicated, but it's at that point that she becomes at least somewhat engaged in the sexual activity with him, but never in my view as a temptress only as a victim. Of course. And it doesn't explain that she's still 12 and he's late 30s, early 40s. There's absolutely no excuse for that. And it's true when they're on the road. I mean, this is, you know, you have to be, the details are very difficult here. But when they're on the road, the first night they sleep in a hotel called something like the Enchanted Hunter or something like that. It seems as though they're in the same bed together and she kind of comes after him. But we should be clear that, I mean, he has purchased sleeping pills so that he can drug her, so that he can, when he was married to her mother and her mother was alive, so that he could drug her mother and her both so he could get them both to sleep, so he could rape the daughter. And then in the hotel, he gives her pills. And a diner takes her back to the hotel and tries to do things to her. So there's, in my view, there is no point at which Lolita comes to cite, as she might in popular culture, as a temptress. At every moment, she is a 12-year-old girl who is forced into a very bizarre and disgusting play with this man. How does she eventually escape? They're traveling across the country for some years, and then she gets away. Explain that pivot in the book. So she does eventually escape from this crazy, disgusting situation. So when they are in the hotel, you have to really follow the details. Nabokov is a master of this. When they are in the hotel together, the first night that they've taken off from her home, her mother is dead, he takes her to a hotel that I mentioned a moment ago, the Enchanted Hunter. And there's a man in that hotel who notices them. And the way that Humbert Humbert knows this is he has given Lolita some sleeping pills. And he waits for them to take effect, and so he goes down to the bar to have a drink. And there's a man there with whom he engages in conversation, and it becomes clear that this man kind of gets what he's doing, has seen him and Lolita together. He doesn't know the man's name, but it kind of freaks him out because everyone else seems to just think that Humbert Humbert is Lolita's father. And that's, you know, because he married her mother and she died. Now he's the adult. So he goes back up to the room, thinks nothing of it, engages with Lolita. They take off. He notices over the course of this road trip with her across America, that there's a car following them. And he's not sure who this is. This is made all the more interesting by the fact that they do stop in a town to live for a few years. It's called Beardsley. And in that town, he notices that there's a playwright who has written a play for the school that Lolita attends. And that play features a young girl who's kind of a temptress of a young girl. And Lolita is set to play the lead role. And so he wonders, who is this playwright? And she meets him and, you know, all this sort of thing. But it turns out, long story short, that they take off again and he notices this car following them. And what has happened is that the guy that saw them at the Enchanted Huntress Hotel, all those now years ago, has been keeping eyes on them, even writing play about her, writing a play about her. And so one night, Lolita becomes very sick. She's got a fever. It's really horrible. And she has to go to the hospital and Humbert catches whatever she's got. I don't know if it's the flu. I don't know. It's really terrible, but he goes back to his hotel room and he wakes up by the time he's able to move out of bed to go check on her at the hospital. He gets to the hospital and the nurse tells him her uncle came and got her. And he puts it all together. And he realizes she has no uncle. It's been this guy who's been following us the whole time, who at various stops, come to think of it at road stops and diners and gas stations, I've seen her talk to, or she's disappeared from my sight. And so she escapes. And then for some years, he goes to search for her. This was sort of another sad plot point because it's not, it is an escape, but it's also, So the man we're talking about, his name is Claire Quilty, and he is also another abuser. So she goes essentially from one abuser to another. And then, you know, to move us along in the storyline, she then again, I would maybe escape isn't the right word, but leaves Claire Quilty, and she marries this guy, Dick Schiller, who is her own age. He's young, working class guy. And at this point, she's around 17 and she gets pregnant. and they're quite financially strained. And she reaches out to Humbert for money, you know, and over these years, he's been looking for her, like retracing their path through their cross-country trip. Can you tell us about that moment in the book where Dolores and Humbert Humbert meet again those years later where she's pregnant? Sure, yeah. So they do meet, and you're right to say Claire Quilty is a pornographer and she goes from one bad situation to another. but he does track her down. He tracks her down because she sends him a letter that says, you know, I know it's been a long time, but I need money. I'm now married. I'm pregnant. And so he finds her and he goes into her home and realizes, first of all, that she's now 17, that she's pregnant, that she's married to a man who went deaf in the war. and they start talking and he says, look, who was it? Who was it that took you? And she's like, I don't, it doesn't matter. It doesn't matter, it's a path, who cares? And he's like, give me the name. And she's like, what does the name matter? And he's like, give me the name. And so he finally deduces this. He ends up giving her the money, but most fascinating to me is that he also says to her, come with me now, leave with me now. I'll take you in. And he seems to say to her, I mean, he seems to be implying, I know you're pregnant, come live with me in a normal family. He seems to be like, we can be a normal family together and I can almost like raise your child or I can be its father too and the way I was your father. And then I think he even sort of starts to fantasize in a bizarre way that maybe that child will be another Lolita, that the child that she's pregnant with will be another Lolita. So it gets very bizarre. She says she doesn't want to go with him, and so she doesn't go with him. And he leaves and goes to search out this man, Claire Quilty. There's one interesting point here that people have a lot of discussion and disagreement around, which is that, you know, he discovers her at 17. She's still a child by, I think, our contemporary understanding. He would say that she's outside of her nymphette stage, right? And he sort of describes her as such as being like a little bit haggard. Um, and yet he still professes his love for her, despite her no longer being a nymphette. Why do you think Nabokov did that? I think it's confusing for the reader because people don't know how to understand his devotion to her. Well, you know, you asked me earlier about the humanization of Humbert, and I think that this is part of it. Namely, his love for Lolita as a 12-year-old girl and the things that he makes her do and the things that they do together is sickening But we have this image that true love endures And so there some bizarre way in which Nabokov asks the reader the question does Humbert devotion enduring devotion over years even as Lolita ages he seems to remain in love with her? In a way, they seem like, from his point of view, to use a kind of trite term, soulmates. I think Nabokov is making us ask ourselves in our own soul, does that legitimize all this? Does that make this okay? That this is true love, that he truly, and of course in my heart, no, it does not. But I think you have to ask yourself, this man is sick about this person, devoted over years. He's going to go murder a man on her behalf. He's going to go kill. That's a big thing. And so I think that the reason the Bokov does this is to make us think about the nature and limits of love and to what degree are Are we willing to say, you know, true love is a cure and it's okay no matter who you love and no matter what you love? Well, in this case, it's a bridge too far. But Nabokov, put your feet to the fire on that. So Nabokov in interviews had described Humbert Humbert as a vain and cruel wretch who manages to appear touching. And we spoke briefly at why he put him behind the steering wheel as the narrator, despite him being unreliable. And I think critics would ask, can you have a book that is anti-pedophile and also narrated by a pedophile? I think that tension and question in and of itself has led to so many people feeling offended by this book. What do you think of that question? I think it's brilliant on Nabokov's part. He doesn't ask someone who's not a pedophile, what is the situation with pedophilia? He says, or he takes us into the mind of such a person, and therefore we become acquainted with the crime and with the mental situation of the individual in a much more intimate and complex way. And so I do think it's possible to have a book that's anti-pedophilia at the same time that it's narrated by a pedophile, largely because you get to acquaint yourself with the darkness of the soul in a way that moral purity, that is to say, refusing to read a book of this kind, wouldn't wouldn't have. Now, I do want to say this book is not for everyone. This is a book that requires you to have what one of my favorite philosophers called a tethered heart and a free mind. It means that at every point you can think about Humbert, and you should be thinking about him critically, but you have to tether your heart, lest you be carried away by him. You asked me about Nabokov's moral intention in a way, is the book Anti-Pedophilia. I think Nabokov doesn't he was asked this question and he claimed not to have had a moral intention. I have this quote here by him where he said, no, it's not my sense of the Humbert-Humbert-Lolita relationship that is strong. It's Humbert's sense, meaning it's not me who reacts to this relationship. I don't have a view of it. I present Humbert's view of it. He says he cares about her. I do not. I do not give a damn for public morals in America or elsewhere. Now, you can condemn him for saying that, but in a way, it's the statement of an artist. He's saying this is the presentation of a situation. It is not my job to be the moral police. It is my job to present you and invite you into the situation and let you make up your own mind. And so I do think that the book can be anti-pedophilia. It may well be pro-pedophilia. After all, many people have read it that way. But Nabokov himself seemed to say, it's not my job to make up your mind on that for you or to be the moral police. I think that's sort of the perfect segue to how the book has been misinterpreted over the years. Since its inception, it seems that people have misunderstood the purpose of this book. Nabokov's European agent sent him a note about the publisher's response to the manuscript when he was trying to publish this book, which was actually quite difficult for him to do. And here's what the note said. He finds the book not only admirable from the literary point of view, but he thinks that it might lead to change in social attitudes towards the kind of love described in Lolita. So clearly this publisher read it more as a vindication versus a condemnation. Similarly, decades later, it seems that Jeffrey Epstein was reading the novel not as a moral indictment, but as erotica. What do you make of that, that misinterpretation that has just stuck through decades? And it sort of begs the question of impact versus intent, right? Right. Nabokov, his intent may be to depict a pedophile in a way that is sort of like a devil in plain sight, but other people have, I think, in a way, read it totally differently. And I wonder how you think about the impact of the book despite the intention. Well, I think this is the case with any great piece of art. It's almost like a child and raising a child. When you have it, you can shape and cultivate it, you understand it a certain way, but you will then release it into the world when it's raised in the case of a child or when it's completed in the case of a work of art and it's finished. And what it does is not up to you anymore. And the kind of thing that it becomes is not up to you anymore. And so in my view, Nabokov was telling this story which came from somewhere deep inside of him. And I know there's a lot of speculation about his own background and his own life and that sort of thing, gave this thing to the world, and then it became alien to him. And that's probably very natural to him. He had done it a hundred times before that. And so I hesitate to say, I mean, I know we've discussed what is his intention versus its impact. I hesitate to say what his intention is because I'm not sure that he had an intention other than to write the best novel that he could and be immersed in an emotion that was complex and perplexing and present it in all of its multifaceted complexity. How others interpret it is not in his control. It's not in any artist's control. And so, you know, I grant Lolita has probably had some anti-pedophilia impact, and it's probably, I mean, it's definitely had some pro-pedophilia impact, but I trust Nabokov when he says, I don't give a damn about public morals. I mean, as an artist, that's his statement. And it may be wrong, and we probably should give a damn about public morals, especially when they concern 12-year-olds. But that was his view, and I'm tempted to try to understand him as he understood himself. Circling back to where we started, what do you make of Epstein's fascination with this book? It seems like he had a more superficial reading, like it was almost like erotica to him. What do you make of that? That's a good question. I mean, I don't know the man, and I hesitate to enter into his psyche, because as you can see, people like this, as Humbert Humbert shows, are very complex. But I will say this, that if he were reading it only as erotica, he would have missed the profundity of the thing. After all, the erotica, this was written in 1950. It's not like a romantic novel or romanticcy today, where, I mean, it's just all the description of all the pulsating parts and all that. That's not what's going on here. And so if you're reading for that, it's fairly subdued erotica. But I think if that's all you get from it, you miss it because there are places at the end of the novel that maybe Epstein should have read with more care where Humbert Humbert seems to say, I know that I ruined her life. I know that I robbed her of childhood. I know there's a very beautiful passage on the second to the last page when he hears children playing in the distance and he hears the swing and the crack of a baseball bat at a park and the sound of children running and dogs barking and leaves rustling and them chasing each other. And he says, what's most missing from that is that Lolita's voice is not among those children. And that indicates that he knew what a monster he was and what he took from her. And so I think if you're reading it just as erotica, you miss the fact that Humbert begins to see and begins to reflect on the fact that he's a monster. And his relationship to Lolita is not one of mere superficial and occasional sex. It's one of interior torment. He's tormented by what he himself acknowledges is a perverse neurosis, a perverse pathology. This episode is brought to you by Of Roughnecks and Riches, the incredible new book from Dan Doyle. Picture this. It's November 2008. The economy is in free fall. You're lying awake at three in the morning, your family asleep beside you, and every dollar you have is riding on a deal that's fallen apart in Oklahoma. What do you do? You quit or you bet everything on yourself? Of Roughnecks and Riches is the true story of how Dan Doyle built a fracking startup from nothing during the worst financial crisis in a generation. It's raw. It's real. And Gregory Zuckerman of the Wall Street Journal calls it, quote, a rollicking ride that makes for a compelling read. If you love stories about grit, risk, and the American entrepreneurial spirit, this is one for you. This isn't a business book written from a corner office. It's roughnecks, con men, busted deals, and a father fighting to keep his family afloat. Never give up. Never stop. When going through hell, keep going. Grab your copy right now on Amazon, Barnes & Noble, or Simon & Schuster. Do it today before you forget. You won't put it down. I want to pivot a bit to the other way that Lolita has sort of just had such a fixture in American pop culture, become such a fixture in American pop culture. What makes you say I've stopped caring for you? Well, you haven't even kissed me yet, have you? I put together a list of everywhere we see it come up. You know, there are two film adaptations, one by Stanley Kubrick, another one by Adrian Lin. Lana Del Rey has a 2012 song called Lolita. She also references Lolita in her other catalog of music. Katy Perry talks about her obsession with Lolita. Lena Dunham has called it one of her favorite books. There have been musical and stage adaptations, ballets, fashion subcultures. even this past weekend, which was Valentine's Day weekend, a famous indie movie theater in Brooklyn played Lolita. Why do you think it has such a prominent place in American culture? That's a good question. It seems to me that there's a glamorization of the girl because the girl is somehow tempting and tantalizing to the man. And so that glamorization requires us to forget who Humbert Humbert is. It requires us to negate from our minds the fact that the girl is only possible because a man has fallen in love with a 12-year-old child. And so I think that the contemporary kind of glamorization, fetishization of Lolita, attempt to imitate her, to hold her up on a pedestal are misplaced because they overlook the fact that she only possible because a man abused her because a man took advantage of her And so I mean you know as the father of a young daughter I mean it not funny And it not something for music videos or it's not a branding opportunity. This is really serious. And I think those people probably just see the name. Maybe they've never read the novel. They see the name Lolita. They know she was a young girl. They know she was a girl of some beauty. I mean, after all, Humbert describes her in the way that if you were a mature woman, of course, you would want to be described beautiful and, you know, the color of her skin and her hair. And if you were, you know, 25, it might be flattering, but this is a child. Well, I think part of the myth around Lolita is dependent on the erasure of Humbert-Humbert in pop culture, right? We always hear about Lolita, but we don't hear about Humbert-Humbert. And, you know, one interesting thing is I think Lolita's use a shorthand for a young woman who is like the archetype of female sexuality, but not necessarily someone who's underaged. It's been like totally changed in meaning. And we don't have Humbert Humbert as shorthand for like an abusive predatory figure. As you said, maybe people haven't read the book. Or, you know, one thing I wanted to put to you was the movie adaptations are quite in some ways a bit of a departure from the book. You know, Stanley Kubrick's 1962 film either fundamentally misunderstood the novel. I mean, Kubrick is quoted saying, to me, Lolita seemed a very sad and tender love story, and the movie comes across as a dark comedy. And that seems to be sort of the impetus for misunderstandings for decades to come. Why do you think he got it so wrong, Stanley Kubrick? That I don't know. That I don't know, but it calls to mind your earlier question, which is when Nabokov released this into the wild, not only did he make it such that any of us could understand it however we want, he made it so that other artists could remake it. And he has no control over that. You point out that there's a way in which Kubrick glosses over it, which I think is right, largely because some of the scenes would be simply unmakeable. You could never put a child in the situation required to do something like this. Even if you had an adult actress, it would be exceedingly bizarre because you would be making her into a child or trying to make her into a child to imply what's going on here. So I think there's a certain fascination with the story and an impulse to tell it. But this is one of the situations where I think the book is simply unmatchable. The things that Nabokov can do, because he's a writer, he relies on your imagination. He doesn't have to put it on screen. He doesn't have to select an actress. You are the film. Your head creates the woman. You imagine what she must look like. And so he makes you responsible for, in a way, the moral violation that in a film the director is responsible for. And that's, in this particular case, the way a book can be a more profound document, an inquiry into this phenomenon than Kubrick's movie or anyone else's movie can because you yourself have to become the casting agent. You have to become the director. You have to become all of those sorts of things. And Nabokov is brilliant for putting this inquiry, which is an inquiry into the depths of human evil in this particular form. Do you think part of the affection for the story is that we are sort of obsessed as a culture with sexual taboos? Yeah, I think that's part of why this is fascinating and popular. Although I would extend that from sexual taboo to a culture obsessed with the allure of moral violation simply. I mean, we mentioned true crime and those sorts of things a moment ago and that that genre is the great. But, you know, I should start a true crime podcast because I'll be number one immediately. That we're obsessed with moral violation, whether it's sexual violation, whether it's murder, you know, whatever the case may be. We want, in a way, to get into the heads of those people and to live lives that we ourselves would forbid ourselves if we're sane, but are fascinated with nonetheless. I think that's probably part of the allure of Lolita. You know, this makes me think about, there's a philosopher I love a lot, Jean-Jacques Rousseau, and he wrote a famous novel called Julie. And at the very beginning of the, it's also a love novel. At the very beginning of the novel, he says, novels are for corrupt people. That is to say, novels are for morally degraded people. There's something to that, that to go and live a life, to see things, to be a voyeur on Lolita or a murderer who's just hacking somebody apart, to have that longing already indicates a certain moral corruption in you. And this art form is peculiarly suited to that. So I think that that's all part of this. One other thing I'll just tack on to the Kubrick narrative is that, as you mentioned, a lot of the plot was omitted. because of the censorship laws. So they couldn't explicitly show that there was abuse. That's one thing. But it's not just what was omitted. It's that they added like a mutual sexual tension in the storyline that doesn't exist in the book, which I think has distorted the cultural perception. And then, you know, the follow on results is that you see, I think young women and girls on Tumblr or TikTok idealizing this, what they would say is like, you know, a love story that clearly is not. All of that is to say, the book is hard to read because it's dark and it's disturbing. It's about child abuse. Big picture, what is the value of putting yourself through the uncomfortable exercise of reading this book? Look, I mean, the premise of old school is that reading good books can make us better. So you're asking me the question, how does Alita make us better? And I would say, well, if we're talking about better in the conventional sense, there are an infinite number of books that I could recommend to men in particular that would make you a better man. I could recommend Jane Austen's novels. You know, I could recommend, if you're interested in love, Cormat McCarthy's All the Pretty Horses. Cormac McCarthy, whose books are like Blood Meridian, which many men will have read, is a profound meditation on human evil. What it means to be a murderer and to be utterly pitiless, unempathetic, hateful. I think that Lolita, it's not that, but it's a meditation on an ugly thing. And I think if you want to acquaint yourselves with all that human nature is and is capable of. Shakespeare saw this, all that it can do and that it can be. The Greeks saw this. Then Lolita has a rightful place in a capacious humanities education because it shows certain aspects of eros, what the Greeks called eros, of erotic longing in their most perverse manifestations. It's worth saying, of course, as I invoke the Greeks, that the Greeks themselves were pederasts. After all, if you read Plato, if you read Socrates, those dialogues, if you read the Achilles, the Iliad with Achilles and his young love, you will find that this has been part and parcel of human history for a very long time. And so I think to see this, to try to understand it, to meditate on it, to tether your heart, not to be seduced by it, not to romanticize it, not to glamorize it, but to tether your heart and try to understand it in a genuine inquiry into the possibilities, both invigorating and oppressing of human nature. Lolita can help you do that, but you need to go into it with a resolution to read it with all of its nuance. You got to do Nabokov justice. He did justice to its complexity and not romanticize it and not simplify it. And I think if you go in with that mindset, you can learn a lot from this. Also, as we briefly touched on, you know, art is not necessarily meant to be moral or model ethical behavior, but more so about evoking feelings. I think the book certainly does that. Why do you think specifically it is a masterpiece and has entered the American canon. Well, you know, Nabokov, interestingly, was asked about this book later in his life, and he could have been given any, he was given every opportunity to disavow it, and he never did. He said, you mentioned it's a masterpiece, that among his writings, it's perhaps his favorite, or one that he certainly regards highly. The reasons he gave, and this will lead to why I think it's a masterpiece, is, you know, Nabokov's second language was English. His first language was Russian. And so to have a novel that's written in this way, he says, this was my experiment with the English language. Like this thing takes your breath away. The way that it's written, just I'm now talking in terms of the craft of writing, just the words on the page and the way they're put together is astonishing to say nothing of the plotting, to say nothing of the story, to say nothing of the exploration of evil. That all of that is there too, in addition to a mastery of the English language by a person who didn't even speak it natively is astonishing in a testament to his genius. I think why it's become, so that's why it's a masterpiece, is that it deals with an emotion that's forbidden. It does it in a very artful way, in a way that is psychologically very, very complex. We do live in a society where there are pedophiles, and it asks the reader to sort of hold the mirror up to society and take a closer look at, you know, it's not always like the boogeyman, but rather it could be someone who comes across as charismatic. And that's like, I think that was one of the biggest messages here is it's like he was hidden in plain sight. One of the reasons I think the novel endures is that it holds up a mirror to, first of all, yourself. What do you make of this? Make up your mind. Is this appealing to you? Is this scary to you? Do you see yourself here? Do you empathize with Humber? Do you hate him? Do you come around to his point of view? Or the whole time, do you think he's a monster? Make up your mind about him. React to this character. Get to know him through his own memoir. That's really powerful because through getting to know him, we come to know ourselves. What are our limits? What are the things that disgust us? What are the things that, what do we think love is? And is this excusable to us? And so we are asked to cross-examine ourselves by way of Nabokov asking us questions through Lolita. So that's one aspect of it. The other aspect of it is that people like Humbert exist in our society, simply. They always will. It's impossible, it seems to me, unless there's some ozempic-like drug for pedophilia to eradicate this from our society. And so insofar as that's the case, better to shine light on it and try to understand it than to deny it and simply sweep it under the rug. The problem is those people who would glorify this rather than be troubled by it, I think, need to reexamine the text. Well, Shiloh Brooks, thank you so much for letting me interview you on Old School. I learned so much from this conversation, and I think the viewer and listener will too. So thank you. Thank you so much for being on Old School.