Six Obsessive Characters in Fiction

How can we not start with Lolita?

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

Leo DiCaprio as Jay Gatsby, the man with everything but the girl.

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

Jude Law as Dickie (left) and Matt Damon as Ripley (right).

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

John Cusack as Rob, the man who would want to be on this list.

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

Judi Dench plays Barbara, the unreliable and obsessive narrator.

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

Captain Ahab (Gregory Peck) is fueled by nothing but revenge.

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.

This sweepstakes has ended.

Comment below for a chance to win a hardcover copy of A Pleasure and a Calling by Phil Hogan, a psychological thriller with its own obsessed character.

To enter, make sure you're a registered member of the site and simply leave a comment below.

TIP: Since only comments from registered users will be tabulated, if your user name appears in red above your comment—STOP—go log in, then try commenting again. If your user name appears in black above your comment, You’re In!

 A Pleasure and a Calling Comment Sweepstakes: NO PURCHASE NECESSARY TO ENTER OR WIN.  A purchase does not improve your chances of winning.  Sweepstakes open to legal residents of 50 United States, D.C., and Canada (excluding Quebec), who are 18 years or older as of the date of entry.  To enter, complete the “Post a Comment” entry at beginning at 1:00 p.m. Eastern Time (ET) January 15, 2015. Sweepstakes ends 12:59 p.m. ET January 22, 2015. Void outside the United States and Canada and where prohibited by law. Please see full details and official rules here. Sponsor: Macmillan, 175 Fifth Ave., New York, NY 10010.

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.


  1. Sally Schmidt

    Good list. Some I knew, some I didn’t. More for my TBR.

  2. Pete Weston

    Thanks for creating another great list!

  3. Jody Darden

    Some great stories here! “A pleasure and a calling” looks creepily disturbing. Would love to read it.

  4. lasvegasnv


  5. Joyce Benzing

    Cool list!

  6. Sherry Schwabacher

    Two of my favorite obsessives – Tom Ripley and Barbara Covett!

  7. Melissa Alcozer

    This could keep me busy for a while.

  8. Shirley Younger

    great winter evening read!

  9. Stephanie N Webb

    Would love to read all of these!

  10. Sandy Klocinski

    A Pleasure and a Calling looks like an interesting (but creepy) story


    Can’t wait to get my hands on this book!!

  12. Bellusion

    Love the list, gotta get busy!

  13. Chris Noe

    These types of lists always make me want to read the books that I have not read yet. Thanks!

  14. Vicky Boackle

    sounds great.

  15. Dawn K

    looks great

  16. g. penrod

    gotta read

  17. Joe Hauser

    Very nice!

  18. cheryl wong


  19. Sharon Kaminski

    I am a avid reader and would love to read.

  20. Leah Jacobson


  21. Sab Edwards

    I think you have to include that movie with Brooke Sheilds ? the one where he burns the house down cus he’s in love with her …stalker guy ..damned what was it called?

  22. Russell Moore

    An obsession of on type or another is at the heart of most great fiction. Good list, though.

  23. KGonyea

    Looks wonderful 🙂

  24. runner

    Groovy Six Obsessive Characters in Fiction!

  25. Karen Hester

    Perfect winter reading

  26. Janice

    Interesting choices. Will have to make sure to read all choices on the list.

  27. Linda Knowles

    Ahab, the most obsessive of the obsessive!

  28. Tom Gibson

    thanks for this nice giveaway!

  29. Stephanie MacDonald

    thanks for the chance

  30. Mary Slate

    So many books, so little…

  31. Tammy Hastings

    This is awesome, thank you for the giveaway

  32. Karen Mikusak

    Would love to win!

  33. lynette thompson

    Thriller, love it. Now were talking a good read

  34. keith james

    Thanks again for introducing me to a new novel.

  35. Haleigh Hillman


  36. Daniel Morrell

    sounds like a fun one

  37. Meredith Peters

    looks like fun


    A WINNER. I want.
    Let me win. I deserve it.

  39. Jeffrey Malis

    Great topic… Thanks for the article and the opportunity!

  40. Anastasia

    I could use a psycological thrill 🙂 Putting my name in the hat for this one 🙂

  41. Julie N

    I feel lucky

  42. jennifer sullivan

    would llove it

  43. Tim Lucas


  44. Leslie Bitner

    Lolita is a great novel.

  45. Karl Stenger

    Mr. Heming is creepy.

  46. Mike Rogers

    Looks interesting.

  47. Diane Chenier

    Yep, need to add some of these to my must read list.

  48. Betty Woodrum

    This is a great list. All the choices are great, especially Barbara Covett – [u]Notes on a Scandal[/u]. I think we’ve all met people who seem to be so caring and concerned so that it takes awhile before it begins to dawn on you that there is a hidden agenda. Thank you for the article and the opportunity to win a copy of [u]A Pleasure and a Calling [/u]by Phil Hogan.

  49. Vernon Luckert

    Looks like some great reads – would love to win!

  50. Becky Hantsbarger

    Brilliant list. Thank you for compiling it and for the giveaway.

  51. Shelley Scaramuzzo

    Fantastic list! No matter how many times I’ve read Gatsby and the Ripley series, they are still just as good as the first read. Same with High Fidelity.

  52. Anna Mills

    The altenater went out on my son’s Jeep, so I will be babysitting my very own grandchildren while he repairs it and I need this book to survive!

  53. Sharon Shumway

    Captain Ahab the most obsessive, I say Gatsby and Humbert Humbert for
    second then comes Ripley and I haven’t read the other 2, but they on my list now. I would love to win A PLEASURE AND A CALLING. Thank You.

  54. snytar

    Sounds great.

  55. Justine Heredia

    This looks great!

  56. Angel Wilde

    Nice looking list of reads. Would love to sing!

  57. David Siegel

    Great choices.

  58. Marie-Louise Molloy

    Read them all, now wanted to get to know Hogan’s obsessive character!

  59. Jeanette Barney

    I am planning to read A Pleasure and a Calling. Would love to win it!

  60. Bonnie Karoly

    I thought Matt Damon was awesome as Mr. Ripley. I was practically gripping my seat when I watched this movie. It was very well done. I need to get the book. I, also, watched Judi Dench in Notes on a Scandal. She sort of extudes creepiness. LOL Well done.

    bluedawn95864 at gmail dot com

  61. Michael Carter

    I would love to win.
    Yes, please enter me in the sweepstakes.

  62. Jenne Turner

    Thanks for the great contest 🙂

  63. Lori P

    Oh, no! I know there are at least a few characters in other books I’ve read that easily fill this bill, but at the moment I can’t think of who they are. I’ll have to obsess on this for awhile.

  64. mali

    Cool list!

  65. Steven Wilber

    Count me in

  66. Sally

    This is a great list, I have read several on the list. I look forward to reading your new book, sounds like it will be on this list too.

  67. Janice Milliken

    Another psychological thriller to add to my list! How lovely!

  68. Karen Koziczkowski

    I love psychological thrillers. I try to guess who the killer/badperson is.

  69. susan beamon

    Interesting list of books. I read some of them back in my college days, not because they were required but because they were more interesting than the books that were required. Humbert and Mr Ripley both killed that boring Augie Marsh.

  70. Lynn Jarrett

    I found a couple of new titles to add to my list of books to read. Thank you.

  71. v cess

    Not one of those guys could top a Jeter fan in 2014. Lol!

  72. Kris Kaminski

    good mix, have to sheck out the ones I haven’t read!

  73. Dan Carr

    Another one to add the the TBR pile.

  74. Gretchen Elder

    How about Annie Wilkes in Misery!?

  75. JULES M.

    sounds really cool

  76. vicki wurgler

    this book sounds great

  77. Michael Herber

    GREAT list !!



  79. Ed Nemmers

    I would like to read the work of Phil Hogan.

  80. Tawney Mazek

    Must add Notes on a Scandal to the To Read list – along with A Pleasure and a Calling.

  81. Donna Bruno

    I never would have thought to put Captain Ahab on there- good call!

  82. Karen Terry

    I loved Moby Dick. I read the book a long time ago. It was the best.

  83. Lisa Pecora

    I would love to read this!!


    This sounds like an intriguing read! Thanks for the opportunity!

  85. Shari Klyn

    My favorite thing to do is read books and magazines. Thank you so much for the chance to win an intriguing book.

  86. Kim Keithline

    sign me up

  87. Valeen Nielson

    Love the list! Some of the most intriguing characters! I’m excited for the chance to win this book! Thanks so much for the opportunity!

  88. Linda Peters

    would love to read these, thanks

  89. Lori Walker


  90. Heather Martin

    HIgh Fidelty makes me laugh at random times, even 15 years after reading it. But, don’t forget John Foweles The Collecter.

  91. Stephen Saunders

    cool list… thanks. Have a rocking day. 🙂

  92. Tricha Leary

    looks great

  93. PaigeEJagan

    Thank you! These all look great!

  94. Buddy Garrett

    It is an interesting list of six obsessive characters in fiction.

  95. Vicki Wise

    Some good reading.

  96. Carrie Conley

    I love thrillers…Moby Dick is what hooked me…

  97. Heather Cowley

    Haven’t read some of those. Will certainly have to!

  98. Tim Moss

    Good deal, count me in!

  99. Daniel Vice

    I would like this

  100. tiac35

    Seems like something that I would enjoy.

  101. Lily

    Thanks for the great giveaway!

  102. CherylMc


  103. Tim Lucas

    Thank you

  104. Debra Kidle

    Looks great!

  105. Mary Ann Brady

    Sounds fantastic. Thx for the contest.

  106. Tyneisha Fondren

    Awesome list, thanks for the chance!

  107. Melissa Keith

    Interesting post. I want to read HIGH FIDELITY.
    I would LOVE to win A PLEASURE AND A CALLING!! I want to read it very badly. I’m OBSESSED with it!!

Comments are closed.