Loveable Rogues: 10 Books with Flawed Characters

My novel Monkey See features a trio of unlikely heroes, one of whom is Danior, a jaded, cocaine-addicted gambler, who’ll pawn his best friend’s beloved ukulele for a hit. Not exactly classic hero material. But he has a good heart, and when the proverbial shit hits the fan (in this case, when a tsunami decimates a city) it turns out he does know the difference between right and wrong.

I’m actually rather fond of a good flawed character: people who do the wrong things for the right reasons, or even sometimes for the wrong reasons, but you can’t help liking them anyway. Here are some of my faves:

The Goldfinch by Donna Tartt

Naughty Theodore Decker is hopped up on pharmaceuticals, doing dodgy furniture deals, and what about what he’s hiding under his bed? But the kid had a hard childhood! And he’s trying to make it right, sort of…

The Rosie Project by Graeme Simsion

Let’s face it, Don Tillman would test your patience. The spreadsheets! The schedules! The questionnaires! But he’s strangely endearing too.

Fates and Furies by Lauren Groff

Mathilde is cold and calculating, and not easy to love. But you’ve got to admire her grit and resourcefulness, especially with THOSE skeletons in the closet.

The First Bad Man by Miranda July

Cheryl is super uptight and more than a little delusional. But compared to her unwanted houseguest Clee, she comes to look like a saint.

Wonder Boys by Michael Chabon

Poor old Grady Tripp. His publisher is hassling him to finish his novel, which is not even close to completion, despite already being about a zillion pages; his lover might be pregnant, but she’s married to someone else which makes it tricky; he deals with these issues and many others by being permanently stoned. Oh, and did I mention the dead dog in his boot?

This Book Will Save Your Life by AM Holmes

Richard Novak’s near-death experience is ironically the very thing that brings him back to life. Beneath the robotic shell which interacts solely with a trainer, a nutritionist and a housekeeeper, lurks an actual human being.

The Life and Death of Sophie Stark by Anna North

Sophie Stark’s schtick is to make people fall in love with her and then bleed them dry. She’s utterly horrible but everything she does is in the service of her art as a filmmaker and her utter dedication to it is kind of admirable, in a twisted sort of way.

Out of Sheer Rage by Geoff Dyer

Dyer is so neurotic it’s almost unbearable, and he makes procrastination into an Olympic sport. But he’s so aware of his own foibles, and so self-deprecating when he talks about them that all is forgiven.

Undermajordomo by Patrick DeWitt

Lucy is a weedy, pretentious liar and sulk who comes of age in the spooky surrounds of the Castle Von Aux. It’s almost impossible to put your finger on what makes you like him despite his shortcomings. But I challenge you not to.

This Bright River by Patrick Somerville

Ben’s bad choices include stealing his business partner’s computer, and setting fire to his office and are mostly executed while horribly drunk. But out of the jail and on the wagon he’s really trying to get his life in order, and I was rooting for him all the way.

Your turn: Who are your favourite flawed characters?

7 thoughts on “Loveable Rogues: 10 Books with Flawed Characters

  1. I have a soft spot for Vernon God Little, in DBC Pierre’s Booker Prize-winning novel of the same name — but I don’t think I’d like him in real life. Same for Rhett Butler, in Gone With the Wind.

  2. Here’s 2 from current reading: Jean Perdue (in ‘The Little Paris Bookshop’ by Nina George) has lost touch with his deeper feelings since his girlfriend left him twenty years ago, even locking away the room they spent a lot of time in. You feel like giving a shake at the beginning but the novel goes on to chart his slow awakening. Christopher (in ‘The Curious Incident of the Dog in the Night’ by Mark Haddon) is an autistic 15-year-old coping with his parents’ separation as well as his self-appointed investigation into the death of a dog without understanding how adults are relating to each other, but you can’t help loving him from the start.

  3. Such a great list, Annabel! No coincidence that of the books on the list that I’ve read, they are some of my current favourites, flawed=real.

    1. I was talking about this recently with the participants of a plotting workshop I ran: the character’s flaws are an essential part of the plot.

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