Literature's Most Prolific Womanisers

Sex is always a catalyst for a good story, but just how horny are the creators of some of literature's most promiscuous characters?
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Sex is always a catalyst for a good story, but just how horny are the creators of some of literature's most promiscuous characters?


To paraphrase Dan Fante (son of the late, great, John Fante) ‘Drinking is good, drinking is very good...but women are the most important drug.’ It’s an age old image; the writer, drinking alone, nights at the typewriter only interrupted by venturing out to chase tail. The Bukowskis, the Fantes and the Henry Millers of the world made their names writing about such adventures and David Duchovny has explored the theme for six seasons of Californication.

As opposed to countless wet rom-com novels, the works of Bukowski and co are supposedly masculine novels, full of horseracing, boxing, drinking and fighting, yet women stand out as the most important characters of many such novels. Bukowski even dedicated a whole novel to them (Women, obviously), claiming ‘Good women--frightened me because they eventually wanted your soul, and what was left of mine, I wanted to keep.’

My middle name isn’t ‘Freud’ (it’s Michael), so I’m not in a position to say why the fairer sex have been such an obsession for male writers, but, if I had to guess, I’d say that it has something to do with tortured minds and souls looking to someone to accept them and lick their wounds. I’m sure Hemingway would (and probably did) say something about sex being the truest form of conflict. But it’s not just sex, it’s women as a species, intelligent and captivating creatures, who take on the role of eternal muse for some writers.

Let’s have a look at some of the most famous women-hungry literary characters and see how they measure up to their creators.

Henry Chinaski


Whatever you come to be doing, it’s always best to start with Bukowski. Digging out books in the library? Bukowski can advise you (Celine or Fante). Getting out of bed in the morning? Bukowski’s got something to say about it. Pursuing women...well, he literarily wrote the book.

I can’t remember how Women begins, because Joel Edwards stole my copy. I think though, that it begins ‘I hadn’t had a woman in five years’. Five years of celibacy! For Chinaski! It was unheard of. To say that Chinaski is a direct translation of Bukowski might be naive, but it is perhaps the closest representation of the writer on the page that I’ve ever read (but then again, most of my ideas about Bukowski are based on reading about Chinaski- it’s a vicious circle).

Over five novels and countless short stories, Chinaski gets up to all sort of mischief with women. Usually, this involves drinking pints of whiskey and fighting, but occasionally he’s been known to get married, get crabs and get divorced. It can be hard to not see Chinaski as a bit of a hard-nosed cunt sometimes, but beneath it all is just a man struggling to get through life as unscathed as possible.

Arturo Bandini


John Fante enjoyed a resurgence in popularity after Bukowski claimed ‘Fante was my God.’ The seeds of Henry Chinaski can be traced back to Fante’s unhinged alter-ego Arturo Bandini, a crazy Italian-American trying to make it as a writer. I’m halfway through ‘The Bandini Quartet’, so am yet to experience ‘Ask The Dusk’ (although this guy has got me very excited for it). Although the details, and to some degree the character of Arturo, vary between the first two novels (Wait Until Spring, Bandini and The Road To Los Angeles) it’s widely acknowledged that Fante poured a lot of his own experiences into the young Bandini.

Arturo’s encounters with the fairer sex begin with his father, Svevo Bandini having his face gouged by Mama Bandini after disappearing for ten days and shacking up with a rich widow. Arturo’s own adventures begin with his school-boy infatuations with Rosa Pinelli, before progressing to jacking-off in a cupboard, imagining a crab is a lusty princess, dry humping trees and rubbing a woman’s head in the sand, all of which make Chinaski look sane.

James Bond


Saying James Bond like women is like saying Bollinger goes well with caviar (does it? I’m more of a Dr Pepper and sardines man). Many comparisons have been made between Fleming’s own career as a naval intelligence officer and Bond’s own SMERSH-bollocking activities, but what about Fleming the womaniser?

It seems like Fleming’s own sexual exploits paled in comparison to those of the world’s most famous spy. Fleming married Ann Geraldine Charteris in 1952 after she left the second Viscount Rothermere for him. Both Fleming and Charteris had numerous affairs but stayed together until Fleming’s death in 1964.

Captain John Yossarian

Yossarian, U.S. Army Air Forces B-25 bombardier, is the best literary character ever created, and Joseph Heller’s Catch 22 is one of the two best novels ever written. Bold claims, but as certain as the sun rising in the east.

Yossarian’s one motivation is ‘to live forever or die in the attempt.’ With death at such close quarters, it’s important to enjoy life as much as possible. Whether this be through the company of whores from the fantastically-decrepit Rome brothel (constantly attempting to evade Nately’s murderous whore), or lusting after a plethora of military nurses.

This scene in which the frustrated officers attempt to stifle their attraction to General Dreedle’s shapely wife, cumulating of a series of lip-biting ‘ooohs’ echoing around the briefing tent, much to the top brass’ chagrin, is one of the best scenes ever written or filmed.


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All Of Hemingway’s Male Protagonists


Bullfighting, boxing, smuggling, big-game hunting, assisting Spanish rebels, fighting in WW1; they’re all the manliest of manly pursuits, but surely all of these testosterone-led activities are a sign of sexual frustration?

Sex plays a huge role in Papa’s work, whether it’s the literal act, the way it affects the relationship between men and women, or the troubles caused by impotency and a lack of the old horizontal dancing. Whilst sex is not the be all and end all of Hemingway’s work, his own string of four marriages suggests he’s not a huge fan of men without women.

Thomas Fowler


Graham Greene’s The Quiet American is up there with the best of his many novels. The protagonist, Thomas Fowler is a journalist, living in Saigon in the 1950s. He’s trying to get his wife back home to divorce him so he can marry his Vietnamese lover Phuong. Unfortunately, Phuong seems more interested in young-buck Pyle. The conflict between young Pyle and the elder, Fowler is a great metaphor for Vietnam’s own slippery descent into conflict.

Despite Fowler’s seemingly romantic intentions, he’s a guy who’s no stranger to ladies’ bedrooms. When Pyle asks him if he’s ‘had’ a lot of women, Fowler replies, ‘I don’t know what a lot means. Not more than four women have had any importance to me - or me to them. The other forty-odd- one wonders why one does it. A notion of hygiene, of one’s social obligations, both mistaken.’

If forty-odd women is not a lot, there’s no hope for any budding Casanovas out there. Despite his own Catholicism, Greene was known to be a bit of a toerag. The Mail claims Greene was ‘a man without alcoholic who abandoned his wife and two children for affairs with a series of married mistresses’. Despite this, Greene still had more morality in his little finger than all the pseudo-outrage in the world can muster.

Patrick Bateman


We’re quite far from happily-ever-after with this one. American Pyscho’s pycho loves sex with high-class hookers almost as much as he loves chopping them up into little bits and microwaving bits of their carcases. It’s classic ‘addressing insecurities by buying loads of sex and making loads of money as a soulless investment banker’ stuff and Brett Easton Ellis carries it off beautifully.

The descriptions of vivid sexual encounters are easily as graphic as the murder scenes, but both arouse different aspects of our human nature. As for bisexual Ellis’ own sexual exploits, he was known as a bit of a New York party boy, before seemingly settling down with his 26 year-old , so make of that what you will.