Sometimes it's love. Sometimes it's revenge. And sometimes it's the refusal to change. Obsession can hijack anyone, and Phil Hogan has compiled a list of six of the most obsessive characters in fiction. Readers can comment below to be entered for a chance to win a copy of A Pleasure and a Calling, Phil's own obsessive thriller. Let's obsess!

Humbert Humbert – Lolita

From his opening words – “Lolita, light of my life, fire of my loins” – the urbane, nymphet-adoring hero (if that’s the right word) of Vladimir Nabokov’s 1955 classic stakes his claim as the grandaddy of obsessives. He is certainly one of the most persuasive. That the reader is made complicit, however uncomfortably, in the sexual grooming and violation of 12-year-old Dolores Haze is a mark of Nabokov’s brilliance – not just in his handling of language and character, but in fathoming the corrupting possibilities of the first-person narrator. How far will he – and we – go? The siren song of the amoral, self-justifying aesthete has been heard high and low throughout literature but with no sweeter compulsion than here.

Jay Gatsby – The Great Gatsby

First love is the worst love, or at least the hardest to shake off. That’s what F. Scott Fitzgerald seems to be saying in this Prohibition-era story of a good-looking boy from the wrong side of the tracks who returns a millionaire to rescue the sweetheart of his youth from a cold marriage. In Gatsby we have a man – with his mansion and champagne parties and colourful silk shirts – who could have any woman he wants. But Daisy – a girl off-limits to the young, penniless “Gatz” – remains “the one” precisely because she’s the one he could never have. It looks like a romance but it’s more desperate than that: it’s about selfhood and the alluring American myth that a nobody can become a somebody. Without the princess, however, there can be no prince.

Tom Ripley – The Talented Mr. Ripley

Personal reinvention is also the driving force behind Patricia Highsmith’s cold-blooded antihero. One minute he’s in New York City sweating a living from petty scams, the next he’s on the Italian Riviera, pretending to be something he’s not. Ripley is no murderer when he arrives with his winning smile and gift of mimicry, but exposure to the high life – jazz, nice clothes, the proximity of family wealth in the shape of carefree dilettante artist Dickie Greenleaf – turns him into one, or at least when this heady, newfound paradise threatens to evaporate. Tom’s slow transformation from Dickie’s wide-eyed admirer into a killer is chilling enough; Highsmith’s true masterstroke, though, is to have Ripley literally step into his dead new best friend’s shoes. One of modern fiction’s most original psychopaths.

Rob Fleming – High Fidelity

With the success of his soccer fan-memoir Fever Pitch in the early Nineties, Nick Hornby established a literary niche for a particular sort of male obsessive. He repeated the trick with a terrific comic novel, High Fidelity, set in a small record shop in which owner Rob and his nerdy assistants, Dick and Barry, spend their hours in competitive displays of pop knowledge and compiling obscurely themed top 5 lists of songs and much else. As the novel opens, Rob’s long-term girlfriend has unsurprisingly dumped him, raising the zeitgeist-y issue of the modern British male’s seeming refusal to abandon laddish preoccupations and commit to a grown-up relationship. Hornby may not have invented the bite-sized cultural “list” – an obsession that now plagues every magazine, newspaper and website, including, of course, this one (Editorial Note: Hey now! Obviously, you haven't seen our 6 reasons why lists aren't such a bad thing.) – but he is impressively guilty of getting that ball rolling.

Barbara Covett – Notes on a Scandal

My apologies for the paucity of female characters on my list, but this one will more than do, I think. The clever thing about Zoe Heller’s 2006 novel is the slow realisation that the story you think you’re reading is not quite the one being told – a sign, as it turns out, of a deliciously nuanced, unreliable narrator. Here is Barbara, a respectable older schoolteacher, recounting the calamitous doings of her younger colleague Sheba, who has been having sexual relations with a 15-year-old boy in her art class, and is now in the middle of the erupting brouhaha. The more insidious infatuation, though, is that of Barbara herself, revealed as a lonely manipulative spinster wheedling her way into Sheba’s enviable sunny life. Soon she is quite the mother hen, sheltering Sheba from the media storm and betrayed loved ones. Well, what are friends for?

Captain Ahab – Moby-Dick

No account of fictional monomaniacs would be complete without throwing oneself to the four winds of Herman Melville’s 1851 sea-faring epic of man versus beast. Scholars will laud Moby-Dick for its narrative power, its kaleidoscopic range of allusion, its proto-existential piquancy, and surprisingly detailed chapters about the whaling industry; the more casual reader will marvel at what happens when an enthusiasm for fishing gets out of hand. Somewhere in the middle, though, is the classic revenge novel. Who, having had their leg bitten off by a whale, would not themselves take up a harpoon in grim pursuit of the culprit? Having said that, few readers in Melville’s lifetime thought it was a grudge worth carrying for 927 pages (first London edition). It took a world war and the birth of modernism before the literary world awoke to his rambling genius.

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Phil Hogan was born in a small town in northern England, and now lives in a small town in southern England. A journalist for twenty-five years, he has written for The Observer and The Guardian. He is married with four children.