Dan from Bamboo Blade, despite being Gonk, has Miya-miya for a girlfriend. He also managed to get the American Carrie interested in him. His reason for wooing both of these girls? His resemblance to an armadillo/pangolin. The fact that he's ranked 3rd in his year in school (out of 390), is an excellent artist, is shaping up to be better at kendo than the guy with regular proportions and is a devoted boyfriend sure helps.
Masato from No Bra. Many readers think that there's no real reason for the girls (and guy) of the story to be attracted to him, beyond some cases of Mistaken Identity.
Oliver Inoue from Victory Gundam is a subversion. Sure, he even has a vague resemblance to Henry Kissinger (mentioned elsewhere on this page), but while his looks are repugnant, his personality is quite loving towards Marbet Fingerhut, who genuinely loved him. Also, aside of slapping Usso once after a blunder, he was a caring an efficient Team Dad towards the group. And there's his Tear Jerker of a death to consider...
Satou Kohta from My Balls, although it is unclear if this is natural, or because the Queen Of Terror is trapped in his balls.
Ultimately averted in Urusei Yatsura. Mr. Fujinami has so many pictures of himself with women and his baby daughter Ryuunosuke that he's forgotten which of them is actually Masako, his wife who died giving birth to Ryuunosuke. It then turns out that he never actually seduced them- he hired them to pose for the pictures because he wanted to "help" Ryuunosuke somehow. How was that supposed to work? ...Who can honestly say? This guy is whacked in the head even by the standards of Urusei Yatsura - keep in mind that he forced his daughter to pretend to be a boy because A: he didn't believe a girl could take over his precious tea shop, and B: he made an Arranged Marriage in which he vowed to have his "son" marry a friend's "daughter" and decided he wouldn't let Ryuunosuke's being a girl stop him providing the groom. Nor did said friend decide to let his only child being a boy stop him from providing the bride.
Played straight, however, with the male protagonist Ataru. Considered by most girls the most unattractive boy in Tomibiki. However, he had one of the above average girls in Shinobu as his girlfriend. And when the Sexy Alien Lum showed up, she devoted her life to Ataru despite all of his personality flaws, which arguably is what made him unattractive in the first place. Not to mention in the first movie another beautiful Alien princess ends up falling in love with him by the end of the film.
The Archangel Raphael from Angel Sanctuary. At least at first, before Sara helps him see his real personality. He doesn't look so bad, but boy is he a sleaze. His assistant is not at all surprised to find him with a girl, getting ready to have sex, before the Archangel Michael interrupts. Michael even asks Raphael if he expects him to remember the names of "all his broads".
Comic Books
Wolverine has had a large number of highly attractive love interests (particularly if they're redheads or Japanese), in addition to having a fairly large female fanbase. This even though he's a short, hairy lantern-jawed guy with weird hair and a perpetual scowl. Unfortunately, poor Wolvie can never settle down and snuggle because his enemies will harm and/or kill them, or he'll just outlive them due to his extreme Healing Factor that makes aging MUCH slower for him. Not only that, he apparently has deep issues with taking a simple bath, and it's mentioned he rarely brushes his teeth. The live-action movies seem to write this out (can't pass up the chance to do a Hugh Jackman shower scene).
Archie. At one point Betty and Veronica realise that he's a stupid, boorish, rather sexist, average-looking jerk and they both decide they should break it off with him... and say "You first." They then wonder why they can't give him up. Archie shows up, they pounce, and he thinks to himself that his good looks, intelligence, and charm have done it again.
Deadpool is one of the ugliest men in Marvel (which is why he rarely removes his mask), he's insane and not very mature. Yet all of his love interests are extremely hot women.
Bianca Castafiore of The Adventures of Tintin may be an extremely Rare Female Example of the trope. Despite neither being much of a looker nor very compelling company, she has quite a few male characters clearly enchanted, including Calculus and Colonel Sponsz. Granted, Calculus's reaction to General Alcazar's wife Peggy suggests he just may have a very unique taste in women.
One time, Tony Stark attended a party with Dazzler as his date. Everybody is shocked, not only because they think Dazzler is way out of his league, but because Tony is disheveled, sleep-deprived, and has forgotten to take a shower. Sebastian Shaw calls him a kavorka man, assuming that Dazzler was taken in by his wallet.
Norman Osborn gets laid a lot more than you'd expect, considering he's in his forties with a 20-something son. But he went down with such megababes as Gwen Stacy and Lily Hollister. Both of whom were young enough to date his son.
Zelig: I would like to apologize to everyone. I... I'm awfully sorry for, for marrying all those women. It just, I don't know, it just seemed like the thing to do.
Austin Powers from the Austin Powers movie trilogy is a physically unattractive man by modern standards but considered a sex symbol in his day due to his self-confidence, merry personality, and "mojo." Vanessa lampshades this in the first film and still falls in love with him. He bags a number of beautiful ladies throughout the series who treat him like a stud muffin.
Pavi Largo from Repo! The Genetic Opera is a sex-obsessed, hideously disfigured maniac whose bearing borders on Flamboyant Gay and who wears the faces of dead women stapled over his own scars, and yet in virtually every scene he's in, women are giggling, hanging on his arms and fondling him. The fandom seems to agree with them. In all fairness, he is played by Nivek Ogre, who fairly oozes charm and his father signs their paychecks.
Cal: Look at me. Really look at me. I am ugly as fuck by traditional standards, but, I get with women. Aren't you curious as to how that's possible?
Groundhog Day: Phil Connors, played by Bill Murray, manages to bed a whole lot of women who have known him for only a day despite looking like, well, Bill Murray. Here, however, it's more plausible because he takes advantage of his Groundhog Day Loop to have infinite opportunities to find out what will please the woman he's currently targeting.
Evan's roommate Thumper in The Butterfly Effect, who's seen making out with an array of hot girls despite being an obese guy in goth clothing.
The Three Stooges (but especially Curly) were known for this, both on and off camera.
The Italian film Seven Beauties, with Giancarlo Giannini as an overweight, selfish guy who is himself a bit mystified at how easily he can seduce women.
In American Graffiti returning older, college student returning to his old high school that Curt Henderson (Richard Dreyfuss) talks to at the high school dance is first seen surrounded by admiring girls even though he's not remotely handsome.
Watch any Adam Sandler movie since the early 90s. Every single character manages to hook up with or already be married to the hottest chick in the film....and it's viewed as perfectly normal.
Det. Gamble from The Other Guys - to the frustration of his partner: both for the trope's own sake and the fact that Gamble doesn't even notice how hot the women in his life actually are (He thinks his wife, played by Eva Mendes, is "just okay.")
Vincent in Twins. The fact that he's played by Danny DeVito would normally be enough. But it must also be mentioned that his first time was at twelve years old... when he seduced a nun.
Ben from The Graduate. He's unemployed (having just graduated) and doesn't seem to have any prospects, and is never presented as particularly handsome. The script makes it pretty clear he was a virgin (he denies it, but not convincingly.) And yet Mrs. Robinson seduces him, and then later her daughter ditches her whole life, including the man she literally just married, to run off with him. Their actions don't have much to do with him: the mother is lonely and looking for some young meat, while the daughter is dissatisfied and looking to rebel, an act she clearly begins to regret in the closing shot.
The characters played by Sid James in the Carry On films are usually pretty successful with much younger women, although James was middle-aged at the time and certainly no oil painting. Up to a point, this reflected Real Life.
Stan and Jack in the On The Buses movies. Both too old and ugly (especially Jack) but always have the hot birds fluttering after them.
Joey Boca (Kevin Kline) in I Love You To Death starts the film with a (hilarious rambling) confession that he committed adultery "ten or twelve times, give or take a few" in the past two weeks.
Literature
In one of the Gotrek And Felix's novels, the infamous duo comes across another Slayer who fits this trope to a T: short, ugly and dirty, he manages to get it on with a remarkable amount of courtesans, to the point that Felix can't believe it.
Gone with the Wind: Scarlett O'Hara is a rare female version of this trope. While being described as 'not beautiful' and treating the people around her like garbage, most of the males in the novel become smitten with her. This effect is ruined in the film as she is played by Vivien Leigh.
While it's said that she's "not beautiful", she's just as often described as "pretty" or "handsome", so it's probably more that she's merely not a conventional beauty rather than outright unattractive. See: Hollywood Homely.
Sir Lancelot in The Once and Future King by T. H. White. He is known as le Chevalier Mal Fet, "the Ill-Made Knight", as he is short, bow-legged and catastrophically ugly, to the point of almost being simian. Still, he gets it on with the beautiful Guinevere, just like the traditional myths.
Embarrassingly common in Hardboilded Detective stories a la Raymond Chandler. The private eye may be a drunkard, a crackhead, and a self-pitying, self-absorbed fool, but the housewife next door, the beautiful reporter, the mysterious suspect ... in fact, every female character in the book under the age of sixty (or under the age of thirty-five, the sets are equivalent), seeks his tender ministrations.
Severian, the Designated Hero of Gene Wolfe's The Book Of The New Sun, describes himself as physically ugly. He's also somewhat misogynistic, and after he's exiled from his position as an apprentice torturer, he takes a paid position as an executioner. The number of women who don't seem to mind is truly impressive. May be a subversion as Severian is an Unreliable Narrator and at least one of his conquests is a possible rape.
Nicholas van Rijn from the Poul Anderson's Polesotechnic League. He's immensely fat, has a big nose, lives on strong cheese and beer, and takes snuff by the fistful. He's greedy, gluttonous, lecherous, and speaks his own brand of garbled Anglo-Dutch — yet he's constantly surrounded by lovely mistresses. His vast fortune has something to do with it, but he often seduces women by his sheer awesomeness too.
Detective Terry Biggs of Lomax And Biggs is stated to look like a mule. He's been married four times, and they all fail (it's apparently the woman's fault, however). It's his voice and charm.
In Havemercy, we have the almost outright sociopathic Rook, who not only treats women with a brutal kind of scorn, but comes very close to killing his new professor and long-lost brother Thom out of sheer rage; the ladies, including the Esar's niece, are not in the least bit bothered by this. Though admittedly, Rook is described as being almost painfully handsome and with that whole rugged airman thing going on...
Arthur Hailey's Overload has Nim Goldman, who's on poor terms with his wife. He looks like a middle-aged Judd Hirsch, according to some covers, and has sex with an absurd amount of women over the course of the book, including a quadriplegic who still has sensation. After she dies, he pours out his story about his affair with said woman to a female reporter. She suggests he go home. He says it's too far away. She suggests he come to her place, which is only five minutes away. He barely hesitates before accepting.What a classy guy.
Mr Wednesday in American Gods. He does it by charm. Literally.
"Charms can be learned."
Bella from Twilight could count as a Rare Female Example. She describes herself as 'plain,' is a complete bitch to everyone, and yet she has boys flocking to her. Heck, five guys ask her to the school dance in the very first book! However, it's heavily implied that she's much more attractive than she gives herself credit for.
It's also worth noting that she had just moved to a very small town, and some of the boys were thinking about asking her out before they'd even met her. It's safe to say that a lot of the interest came from her being a novelty.
Maybe there's something about books that lets women get away with this. Myrtle Wilson of The Great Gatsby is described as being rather fat and not particularly attractive physically, but possessed of a burning vitality and gregarious personality that makes her a joy to be with.
Berrynose of Warrior Cats. He has no tail, but he does have a huge ego. And she-cats love him.
Victor Krum from the Harry Potter series. He's rather ugly, and pretty awkward socially. However, he is a great Quidditch player, and thus has lots of fangirls due to this. He even manages to successfully ask out Hermione, who had said earlier in the book that he wasn't good looking.
Count Dracula in Dracula. His physical description shows him as being rather ugly, even after he grows younger, and he has hairy palms. However, he has three vampire wives and manages to put several women into his hypnotic spell. He's more of a dirty old man/sexual predator than the modern Vampires Are Sex Gods trope.
It should be noted that aside from the women in his castle, there are no women interested in him. His 'hypnotic spell' is a violent assault that turns women into vampires.
In The Flea Palace by Elif Shafak, Edith is a Rare Female Example of not only this but also a Millionaire Playboy. She uses her wealth to welcome a crowd of men to her house (prefers intellectuals) and they're fascinated for no known reason and want to sleep with her although she's extraordinarily ugly.
Vorkosigan Saga: Miles Vorkosigan was poisoned before birth, causing him to have abnormally small stature (self-described in the narration as "ahem-mumble-something under five foot"), a bent spine, one leg several inches longer than the other, a too-big head on a too-short neck, and a face prematurely lined with pain from more bone breaks than he can count. He still manages to sleep around with several gorgeous women throughout the course of the series. It's mostly that his sheer charisma and force of personality completely overwhelm his physical appearance once you actually get to know him.
Nearly every male protagonist in any book by Tom Robbins, but most particularly Half Asleep in Frog Pyjamas.
Gabe Uglino in the first book of Percy Jackson and the Olympians he's ugly, drunk, can't hold a job, abuses Sally (it's implied he abused Percy too) yet he gets both Sally and Sugar. (his grief counselor)
Another female example appears in Bridge of Birds - Lotus Cloud, the so-called "most expensive woman in China" looks like exactly what she started out in life as - a broad-footed, flat-faced peasant, so plain as to make a mud fence look attractive. The hero/narrator looks at her and finds himself wondering why anyone wastes any time on her When She Smiles directly at him- he immediately throws himself to his knees at her feet and wraps his arms around her thighs, declaring his unending love and devotion to her. She nicknames him Boopsie.
Yet another Rare Female Example in literature: Sugar in The Crimson Petal And The White is described as having "mannishly large" hands and feet, no curves, and a non-contagious yet incredibly obvious skin disease which causes her body to be permanently afflicted with angry red stripes. Yet she not only finds lucrative work as a prostitute, but becomes incredibly popular with wealthy and intelligent clients, since she's one of the few women who provide good companionship and can interact with them as an intellectual equal. Completely Averted in the TV adaptation, however, where she's played by the very attractive Romola Garai.
Trope namer is Kramer, where a Latvian Orthodox priest calls his power over women "kavorka" (meaning "the lure of the animal"). Over the course of the show, he's seduced Uma Thurman, a nun, and a lesbian, offering no explanation other than, "I'm Kramer." This was actually Played for Drama on the episode that named it, since he couldn't control the effect and almost destroyed a nun's life against his own will.
George also qualifies and has also been lampshaded.
Newman has also been out with some very attractive women.
Nick Tortelli from Cheers is probably the ur-example - causes Diane to swoon just by standing near her when she doubts his abilities. His ex-wife Carla has a similar power over men in spite of her personality.
Patrick from Coupling, being charming, handsome and notoriously well-endowed, is mostly regarded as a straight The Casanova, but at other times, when we're reminded that he's a chauvinistic ass with the mental power of a sack of potatoes, his prowess with women seems more like the Kavorka Man.
Tony Soprano. He's an overweight, chauvinistic, sociopathic criminal and yet sleeps with a variety of very good-looking women (not just strippers/prostitutes from the Bing) such as Irina (and her one-legged cousin), Gloria Trillo, Valentina La Paz and Juliana Skiff (all of whom look like his mother, adding to the All Psychology Is Freudian aspect of the show).
Not just Tony; nearly all the mobsters in the show have beautiful wives and girlfriends, despite many of them being ugly, mean or both. It's implied that the women they're with are attracted to the power they represent.
Owen Harper, from Torchwood, seems to effortlessly attract a large amount of attractive women, including all three of his female co-workers at various points, despite that fact that being pale, having weird frog lips and being an absolute prick makes his attractiveness a questionable thing. This could just be Informed Attractiveness, since apparently in-universe women genuinely find him "gorgeous".
Even pushing 60, Kathleen Turner is gorgeous. However, in Season Two of Californication, her performance as Sue Collini is deliberately off-putting, at times evoking Nick Tortelli in a skirt. This turns her extended cameo into a triumphantly flaming ball of distaff Kavorka.
Dr. Guy Secretan from Green Wing may be a wealthy anesthetist- but he is also a womanizing jerk who could fairly be said to look like "Donkey" from Shrek. Believes that women with small breasts aren't worth resuscitating.
Charlie Harper from Two and a Half Men. In his defense, most of these come off as sensible or self-respecting, but his talent as a pickup artist borders on the supernatural.
Charlie's fairly handsome (not to mention rich); it's his personality that's gross. Probably more like "all girls want bad boys" in his case.
A Rare Female Example: Mimi from The Drew Carey Show is obese and slathers on makeup with a trowel(not to mention being kind of a sadistic Jerk Ass), yet has a long list of sexual conquests, including no less than three famous rock musicians, one of whom she was married to for a couple weeks.
Spike Thomson from Press Gang, despite being short, not particularly attractive, and insisting on wearing leather jackets and sunglasses indoors, apparently has no trouble both attracting a string of conquests that he uses to annoy Lynda, and continually stealing Colin's love interests.
Shawn Spencer from Psych is good-looking enough, but he's a sleazy con man who uses pickup lines that Leisure Suit Larry wouldn't touch with a ten-foot pole.
Rene from 'Allo 'Allo! has virtually every woman in the cast at some point (and even gets a few guys chasing him) and is a fat, middle aged, balding, greedy, cowardly fool.
Bobby and Tig from Sons Of Anarchy go through women despite Bobby being fat and middle-aged and Tig being both abusive and downright psychotic. Tig is good-looking for a man his age, though, and he has bad boy appeal.
Cook from the second generation of Skins is forever getting laid.
Det. Nick Vera on Cold Case has a succession of women despite being fat, slovenly, and so very, very uncultured, save for that one time he took a co-worker to see Wicked. Hell, outside of his wife, his longest relationship was with Kima Greggs from The Wire!
Vic Mackey from The Shield: An amoral, malevolent ball of stocky menace, who nonetheless manages to score with a string of women. Taken to an extreme in Season 5 when he seduces the hot wife of Detective Kavanaugh played by Forrest Whitaker, implying him to also be a Kavorka Man. So essentially Vic Mackey out-Kavorkas another Kavorka man. Impressive.
Played for comedy in Stella, which has a Running Gag where the balding and bespectacled David Wain will lock eyes with a beautiful woman and draw her in for a passionate kiss.
Olly Reeder from The Thick of It is a weaselly, pale, bespeckled prick who looks like a twelve year old...and over the course of the series dates both Hot Scoop Angela Heaney and Emma Messinger from the Opposition. This is really very good going in a series that seldom bothers to look at anyone's private lives (because most of them don't have private lives). This does just apply to the character rather than Chris Addison, the actor who plays him and is something of a Bishounen.
In the How I Met Your Mother episode "The Naked Man," a guy named Mitch (who's broke, out of shape, balding, talks about nothing but fantasy football, and it's implied, doesn't have a very impressive male organ) still manages to hook up with Robin and, he tells us, a bevy of past dates by using the Naked Man technique.
Step 1: Arrange a date with a woman.
Step 2: Find an excuse to go up to the woman's apartment.
Step 3: Wait until the woman leaves the room.
Step 4: Strip completely naked.
Step 5: When the woman returns, your sheer bravado (and a little bit of pity on her part) will get her to strip naked. And then it's on! (Two out of three times, anyway)
Life On Mars and Ashes to Ashes feature DCI Gene Hunt, "an overweight, over-the-hill, nicotine-stained, borderline-alcoholic homophobe with a superiority complex and an unhealthy obsession with male bonding" who treats women "like beanbags". The number of times he has spoken to a woman without mentioning something rude can be counted on one hand, and even the people who genuinely like him find him brutish. Tales of his sexual prowess mostly come from himself, but the staggering number of female fans willing to give it up for the Gene Genie possibly make him a semi-real-life example.
There was a nice inversion of this trope with chain-smoking, butch WPC Phyllis Dobbs. She nevertheless refers to herself as a "sex goddess" and has a healthy appetite for it, which even Gene acknowledges in his backhanded manner.
Todd Packer is a bald, overweight, incredibly chauvinistic jerkass. This does not stop him from scoring with, we're told, whole crowds of women.
Dwight. He's weird-looking, creepy, borderline psychotic, but virtually every time he bothers to pursue a woman, he's successful. To the point where he once had an entire WNBA team clamoring for his phone number. This seems to just be an aspect of his hypercompetence.
Frank is overweight, sees women as mere objects, has terrible hair and wears those weird hats. He also has "a lot of irons in the fire."It helps that his preferences run towards fat, past middle-aged women.
It is once lampshaded that Liz Lemon is female example of this trope. She is usually made out to be ugly and unattractive or having a poor personality, and yet she certainly has had a lot of conquests.
On The Golden Girls episode "Love me Tender" Dorothy dates a short, bald man who is still pining over his ex-wife (played by John Fiedler, aka Piglet). Yet they have fantastic sex and the other girls grow extremely attracted to him, with even Sophia leaping into his arms and wrapping her legs around him to give him a hickey.
On Arrested Development, Tobias is arguably one, he doesn't go out seeking people, but a lot of people throughout the series just fall in love with him, e.g. Gob's wife, the marriage counselor that he sees with Lindsay, and a CIA agent.
Dan Stark from The Good Guys. He's been known to attract women without even intending to, much to the utter bafflement of Jack.
Jack Klugman as the title character in Quincy who despite being a coroner who lived on boat, and looking like Jack Klugman managed to score a lot of women.
Earl Hickey in My Name Is Earl. He's got a receding hairline (with what hair he does have being very unkempt), a Porn Stache, and a very average build. He's lazy, drinks like a fish, and (until a certain incident involving a winning lottery ticket and the front end of a Cadillac) very selfish. He has slept with many women over the course of the series, and even gets his comeuppance for being so horrible to women in the past.
There's also his Fat Idiot brother Randy. He's chubby, he has Perma Stubble and Messy Hair, has a foul temper, and the IQ of a toaster. And he gets almost as much tail as Earl.
A Rare Female Example: Patty The Daytime Hooker. She's a Hollywood HomelyStreetwalker who is obviously in her 40's or 50's, and she's very open about being a prostitute. Yet she's slept with every straight and bisexual man in Camden...and all of them enjoyed it (even when she turned out not to be the comely young beauty in her newspaper ads).
Another female example. Leslie Winkle from The Big Bang Theory as she is (debatably) average looking with an unlikable attitude, and yet Leonard and Howard went out with her for a while and she boasts about having slept with different people in the majority of the time she appears.
Howard himself might also count as either this, or a Casanova Wannabe, depending whether you believe he's a sexually active as he says he is.
Sheldon is halfway to being one. Despite his infuriating/wacky/obsessive/borderline psychotic personality and taking no care in his appearance, he has a remarkable number of admirers, charming several attractive women and, during an incredibly blunt, thirty second conversation, a man. The reason he is only halfway to being a kavorka man is that he didn't realize, in any of these instances, what was happening, due to his social skills (or lack thereof), and never actually consummated his inadvertent "flings."
VH-1's reality show The Pickup Artist was basically the idea of turning average guys with little to no game into Kavorka Men.
Flavor Flav of the hiphop group Public Enemy, who starred in the VH-1 reality show Flavor of Love, where each season, twenty skanks (most of whom are almost half his age) fought over the affections of what must be the most unattractive man on the planet.
Pierce Hawthorne on Community has been divorced seven times. This means seven different women agreed to marry him in the first place.
In the second season he was shown to be engaged to a woman after only one date.
Stan and Jack in the On The Buses TV series. Both too old and ugly (especially Jack) but always have the hot birds fluttering after them.
Quark in Star Trek: Deep Space Nine is a short, badly-dressed, sexist pig with humongous ears and scary-looking teeth, but he, too, was usually seen with hot women over the course of the series. He's also an alien Ferengi, however, born into a culture where women are second-class citizens with no rights, so in that sense he's not unusual. Working around humans and other alien races in which equality of the sexes is a given, however, does make him unusual.
Most of the women he was seen with were attracted to his wealth and status, but a few were genuinely attracted to him. Probably his most impressive feat was landing a Klingon mistress, Grilka. In a society which lauds physical strength and detests the cowardly Ferengi on principle, this is totally unheard of (although what attracted her was his courage and straight-up audacity, which are values in both cultures).
There was also the Running Gag of the alien barfly, Morn, always being accompanied by a stunning woman. Supposedly he's a good conversationalist.
Another joke was Jadzia Dax shooting down any and all advances from Dr. Bashir, only to go out on a date with Captain Boday. One of these men is a handsome doctor with a British accent and long line of sexual conquests. The other has a see-thru head.
Franz Bieberkopf in Berlin Alexanderplatz had a string of beautiful women devoted to him despite being an overweight, unhandsome, unemployed ex-con.
More like Casanova Wannabe. He gets shot down by any female character we actually see him go after, and although we hear about his perverted exploits fairly often, we don't see them, and some of them are supposedly with prostitutes anyway.
Jeremy from Peep Show. Despite his receding hairline, spacey British teeth and a clingy, obsessed personality; Jez is consistently involved with many attractive women.
David Cross plays a few of these in Mr Show (and might be one in real life) as Ronnie Dobbs, Derwin in the Lifeboat sketch and possibly Lee in "Our Secret Love." The former is a lazy, white-trash, borish celebrity who had his first wife Tammy, also ended up with a second wife played by Jenny Mc Carthy (and in The Movie has a girlfriend played by Nikki Cox). Terry's inexplicable attraction to Ronnie as well might also be part of this trope.
There are a lot of legends surrounding Gene Simmons and his promiscuity. He was once voted #6 in a magazine's "Top 20 Ugliest Musicians" article.
A lot of rock stars fit this trope. Wealth and fame don't hurt when it comes to getting some, after all. Neither does talent.
The hip-hop world probably showcases it even more so these days. The majority of the rappers that actually have some talent these days aren't exactly attractive (Lil Wayne, Jay-Z, I'm looking at you), but the women they've hooked up with are beyond attractive (Jay-Z marriedBeyoncé!).
Notorious BIG was famous for sleeping with every attractive female in hip hop despite being a fat, ugly man, and often made mention of this (particularly the fat and ugly part) in his rap. Of course, it also helps to be known for having what Method Man called "personality like a motherfucker."
Lemmy Kilmister of Motörhead manages to be even uglier than Simmons, sporting a number of huge warts, yet by some estimates has had sex with between 1,200 and 2,000 women.
A woman famously crawled on-stage and began to fellate him mid-concert. It must be his gnarly riffs.
Similar to the Lemmy example, Mick Hucknall of Simply Red claimed to have slept with 2000 women. This was widely joked about when it was reported, because he is not conventionally attractive, especially in England where red haired men are often considered ugly. However, due to his fame nobody could deny that it was at least possible.
Calypso singer Lord Melody had the gimmick of being popular with women but considered ugly. A lot of his songs have women thinking he was ugly and wanted him just for his money. He also had a number of fat women who slept with him just so he could buy food for them. It is hard to know how many of his song lyrics are true and how many are not, but he nevertheless had several children in real life.
As Eddie Murphy stated in his stand-up act, "All you have to do is sing." His Ur example is Mick Jagger.
Joe Jackson's "Is She Really Going Out With Him" is about the narrator's distaste for one of these.
Argentine party classic ¿Qué tendrá el petiso? ("What does the short guy have?") by Ricky Maravilla has the (supposedly handsome) singer wondering what's with the bald, toothless, ugly short guy that gets all women. It turns out, he has a lot of money.
Reggae artist pioneer Shabba Ranks. Known for being very unattractive in the face, but has a reputation of having lots of women, because of his status as the original Dancehall King.
Newspaper Comics
Wimpy from Popeye is an overweight, squinty-eyed moocher, and yet can easily sweet talk any lady that he wishes.
Professional Wrestling
Scott Steiner. Steroided all to hell, loud, abrasive, obnoxious, can't go 5 seconds without insulting somebody, prone to random fits of violence... and he has "freaks" in every town just waiting for him to show up and show them a good time.
Theater
Shakespeare's Richard III is a hunchbacked, evil gnome of a man, and yet he woos the lady while simultaneously delivering a constant Hannibal Lecture to the audience. Keep in mind that Richard's designs on the throne are in part motivated by his ugliness and poor record with women. ("If I cannot play the lover in these fair well-spoken days, I am determined the play the villain, and hate these well-spoken days.")
Literally over her father-in-law's dead body — murdered by Richard's own hand, no less — which, for an extra-romantic atmosphere, happens to be still oozing blood from its wounds. Apparently, Anne just can't resist a Magnificent Bastard. Some productions like to play with the idea that Anne herself is ruthless enough to accept Richard's hand just so that she can have a tiara again.
In Lady In The Dark, Charley Johnson's female colleagues react with various degrees of offense to his habit of making drunken passes at them. However, he has little trouble getting pretty models to go out with him, even after pinching one on the behind.
Video Games
Ernie Eaglebeak of The Spellcasting Series, a scrawny geek in Nerd Glasses that still manages to bed dozens of gorgeous women in his travels.
Jimmy Hopkins of Bully. He's nice, sure, but there's probably a reason for that...
The main character in the Visual NovelRunaway City is blessed with incredible luck, resulting in being able to seduce just about every woman he meets. The game subverts the normal Unwanted Harem when the Genki Girl, Tsundere and Bokukko all start to mutate into his favored type of girl just to please him. It becomes even worse when women he would never have a chance with spontaneously fall in love with him the second he expresses attraction to them. This results in him seeing his ability as Blessed with Suck; it makes every conquest he has akin to rape.
Curtis, the protagonist of Phantasmagoria 2, has a girlfriend, another female coworker and a gay/bisexual male friend all attracted to him (and according to the actor who plays, even the Jerk Ass male coworker who keeps insulting and sabotaging his work does so to hide his attraction to Curtis), even though it's difficult to imagine anyone more generic in terms of looks and personality.
Mario: A short, chubby Italian plumber nevertheless manages to be a Chick Magnet, especially in the Paper Mario games. Apparently, they dig the 'stache.
Ebisumaru from Ganbare Goemon. This short, chubby, and effeminate guy is very popular with the ladies. The same goes for his Evil Twin.
Mad Scientist Hojo in Final Fantasy VII. Despite being middle-aged and creepy, he is shown to be surrounded by adoring, bikini clad young women when on his vacation. The backstory also reveals Lucrecia picked him over Vincent. The original game hints that he was a looker but in Dirge of Cerberus he still looked middle aged and creepy even in his youth and didn't even attempt to hide his repulsive personality.
Motorcyclist "Heartbreaker" Charles in Pokemon Black And White, an overweight, scruffy, middle-aged man who trained in obscure styles of Pokemon battling to impress girls, and offers to teach them to the player character.
Joe Rosenthal is a split between The Casanova and a Kavorka Man: he's got looks, brains and superhuman strength, but he took an approach that was so direct that it should have earned him a lot of slaps in the face. It never did. This may actually be one of his superpowers, though.
Joe in Punch an' Pie. He's a huge guy with an irritatingly uptight manner who nonetheless claims that few women can resist his "charms." The gigantic fistful of phone numbers he gathered in a few hours attests that he is telling the truth.
Jason from Something Positive is pretty similar. He has, as Aubrey explains, the right physique to play Santa Claus, and while he can be a really nice guy, he's also known to play horrible tricks on his friends and basically be an egotistical jerk. Still, he gets lots of girls until he gets married. He claims it's because he worked out a psychological formula which allows him to instantly plug into any woman's attraction, though we've never actually seen this process work onscreen. May have something to do with the fact that he has endowments that have been known to frighten webcam girls and offers his partners a contract promising a "minimum of two orgasms per encounter".
The trope is discussed in Manly Guys Doing Manly Things between Marv,Kratos, the Commander, and Jonesy. Marv is convinced the trope is bullshit. Jonesy claims it isn't and Marv could be one if he wouldn't let his self-esteem get the better of him. The Commander's only response is "Kratos gets girls", and when Kratos tells him to stop using him as an example, the Commander replies that Kratos should stop being an example.
Web Originals
Chad Vader. He's an awkward, deformed Nerd who works as the day manager in a grocery store and can't survive without his suit, and yet the ladies seem to like him quite a bit.
Pom Pom from Homestar Runner seems to be very popular with the ladies for a giant yellow ball with stubby arms...
Big Fat Reverend Burn is a highly unattractive, morbidly obese and pizza-faced individual... who talks about his experiences with women almost as much as he jokes about his own weight.
Do you have any idea how awkward it is to make a sandwich while your penis is inside a woman?! No!
Brian from Family Guy has dated a fair number of human women considering he's a dog.
Chris is sometimes this. Many women (and two guys) have had some sort of attracion to him, despite being fat and looking very much like his father.
Meg is sometimes a strange subversion. Although guys are normally disgusted by her, she sometimes gets dates like it's nothing.
Bender from Futurama. He's a rude, amoral, alcoholic, kleptomaniac robot, whose shacked up with several fembots and even a few human women, though this may be chalked up to All Girls Want Bad Boys.
Real Life
Jack Nicholson, even though he was quite attractive in his youth.
Woody Allen, the nebbishiest of Jews, married Mia Farrow, the ex-wife of Frank Freakin' Sinatra, and then dumped her for her much younger foster daughter.
Justified In the words of notorious Kavorka Man, Henry Kissinger (pictured above): "Power is the ultimate aphrodisiac."
John Wilkes of England and the French Count Mirabeau were famous not only as statesman but for having scores of conquests despite being notoriously ugly.
Wilkes commented on this, and provided an explanation (wittiness/charm) for his success, at least: he said that while at least some women were repulsed by his looks, it usually took at most half an hour to "talk away [his] face".
A female example: The French novelist Françoise Sagan was anything but gorgeous. She had a rather masculine face and a scrawny body with no curves but she had a very active sex-life and most of her suitors were handsome and wealthy men.
Catherine Deshayes, aka "La Voisin", was fat, squat and ugly◊, even by her days' standards. She would help people murder their relatives by poisoning them, she would abort unwanted babies and incinerate them in her oven. She organized black masses and was a notorious witch. Even the most promiscuous would blush upon hearing of just how many men would line up in front of her in hopes of having sex with her.
Artistic impressions of Lola Montez are beautiful, but photographs on the other hand make people nowadays wonder what her attraction was; some contemporary commenters were less than complimentary about her looks too. She probably fascinated by the sheer audacity and aggression of her sexuality.
Samuel Pepys was apparently a real ladies' man despite looking like this.◊ However, he apparently often paid for it, or intimidated his employees' wives into it.
Benjamin Franklin, who had quite the history even in old age. Legend has it that when Franklin returned from his post as the American ambassador to France (a post he was assigned at the age of seventy-two), he was afflicted with every venereal disease known to medicine at the time. He was also rumoured to have frequented the legendary "Hellfire Club." All this despite being bald, old and portly, though he was was considered handsome in his youth.
Gouverneur Morris was a less-known, but important, founding father (he probably wrote the Preamble to the Constitution, "We the People..."), who lost the flesh from an arm in an accident as a teenager, lost a leg in an accident in his late twenties, and started going bald fairly early, and still managed to keep up one heck of a tally.
MLB pitcher Brad Penny is fat, sweaty, and not even that great of a pitcher. Yet somehow, he has managed to nail both Alyssa Milano and Eliza Dushku. And now, he is currently engaged to Karina Smirnoff. Explanations are few and far between.
Gene Simmons. Ghoulishly ugly both in and out of makeup, and so unlikeable that he even lampshaded it by naming a solo album Asshole, yet he's been rumored to have slept with thousands of groupies.
Radek Stepanek, a Czech Tennis player consistently in the top 20 of the world, is not quite average looking at his best, but is notorious for the number of gorgeous female tennis players he has been involved with over the years despite this.
Jean-Paul Sartre was ugly, short and a jerkass even toward his former friend Albert Camus, but had numerous affairs - about which he gossiped with his equally, um, active girlfriend Simone de Beauvoir (see the book Philosophers Behaving Badly for more information). His intellect and fame probably helped.
Many famous authors, including Balzac, Thoreau, Ayn Rand, and H.G. Wells qualify.
On woman was asked what was so attractive about Wells. The only answer she could give was "His skin smelled of honey."
Ron Jeremy, the most popular (male) porn star who ever lived. Sure, his equipment is nine and a half inches, and he was buff back then, but now he is middle-aged, short, and fat. Despite this, he's got a world record for the most porn sex scenes (over 2,000!), and the ladies claim that, once they get past his looks, he's really good in bed.
Alain Prost. This man ran off with fellow French Formula One driver Jacques Laffite's wife.
Fisher Stevens, at least according to Adam Savage and Penn Jillette, who reportedly refers to him as "the pussy-gettingest man alive." He was married to Michelle Pfeiffer.
Most accounts give the impression of a particularly great personality, such as being a "compulsive listener", coming to the rescue of a drunk woman who collapsed in the middle of a New York street, and recently making the extremely adventurous documentary The Cove, exposing the slaughter of dolphins by Japanese corporations, and winning an Oscar for it.
The Russian mage Grigori Rasputin had syphilis, never bathed or brushed his teeth, and wasn't known to have the best manners. Yet he was known to be quite a hit with the ladies.
Although part of the appeal (among the female aristocrats anyway) was in sleeping with a dirty, unhygenic peasant. That's slumming for you.
Former French President François Mitterrand◊. He was short, out of shape, and even in his youth was far from being handsome, but he could have any woman want him to impregnate her just by saying hello. And, apparently, that was so even before he was a supposed hero of the Resistance and a politics.
75 year-old Japanese porn star Shigeo Tokuda. Just read the article.
Former Canadian Prime Minister Pierre Trudeau. The least of his unlikely conquests was marrying Margaret Sinclair (who was a bit out of his league and half his age when they got married).
W. C. Fields wasn't exactly a looker, but was certainly a charmer.
Other French female example: Writer/Artist Catherine Millet is plain-looking at best and was a Butter Face in her younger days. Her book, aptly named "The Sex Life Of Catherine M.", simply relates that this woman had the sex life of a porn star and was a regular client of swingers' clubs and an orgy fiend whose sole days of abstinence were her period.
Diego Rivera◊ was notorious for his conquests, cheating on every wife he had with a series of models.
Italian actor, singer and one-time sex symbol Adriano Celentano, who, in a move of Self-Deprecation, famously quipped that "a man should be slightly more handsome than an ape".
Russian singer and actor Vladimir Vysotsky, who charmed lots of women with his brutal looks and raspy voice.
Norwegian classical pianist Kjell Baekkelund [1]◊ was a major ladies' man.
Some reports of Cleopatra contradict her reputation as a gorgeous woman. She was described as not being particularly attractive with a short stature, a very large nose, and terrible breath, though she supposedly had a beautiful voice and lively personality. But really, with that she bedded Julius Caesar and Marc Antony?
Harold Bloom is a Yale literary critic who quite charitably resembles a oversized turtle. Up until major health problems caught up with him, he was quite infamous for his affairs with graduate students.
Hustler magazine founder Larry Flynt. Though being shot and paralyzed from the waist down has left him unable to have sex for over 30 years...
Serge Gainsbourg wasn't really physically attractive... It didn't stop him to charm beautiful women, including Brigitte Bardot (who was one of the most beautiful popular stars back in the day. Nowadays? Not so much).
Joseph Goebbels, Nazi Minister of Propaganda, was a "remarkably successful" womanizer, managing to wed (and have six children with) his famously attractive wife Magda as well as an affair with a Czech actress called Lida Baarova. All of this despite his really unremarkable looks (and, you know, that whole Nazi thing).
The "whole Nazi thing" does not really count, since almost nobody expected the Nazis to become murderous racial fanatics prior to 1940 at least. Womanizing would have been much more complicated for Goebbels after 1945, had he survived the war.
Actually, the "whole Nazi thing" counted in reverse. The Nazis came to power by popular vote in the early 1930s.
Former Speaker of the US House and candidate for President in 2012 Newt Gingrich has been described (on The Daily Show) as looking like Dwight Schrute on a good day. He nevertheless has had not one, not two, but three wives—two of which he had had an affair while still married to the previous one while the previous one was diagnosed with a serious disease. note His first wife was in the hospital with cancer when he served her with divorce papers. His second wife had just been diagnosed with multiple sclerosis when, according to her, he asked for an open marriage. And according to many in Washington, he kept up quite the tally at least until his third marriage. Again, we must emphasize: he has been compared unfavorably to Dwight Schrute. Not Rainn Wilson. Dwight Scrute.
Casanova himself. No, really, look at the surviving pictures of him. He was frankly pretty weird-looking. He was also perpetually impoverished and emotionally stunted. He moved from job to job and woman to woman his whole life, because he was smart and charming enough to get both but never cared enough to keep them. Women knew this, they just never seemed to care.
Rose O'Neal Greenhow. She was a Southern socialite and spy for the Confederacy during the American Civil War. She was hugely successful because men seemed incapable of refusing her anything. On multiple occasions, she seduced Union officers and politicians to where they were willing to betray their duty (and left a few suicides in her wake). Looking at pictures of her, it's not obvious how.
Serial Killer Angelo Buono (one of the Hillside Stranglers) was sexually violent, misogynistic and merely average-looking—and constantly surrounded by teenage girls too foolish to realize that they deserved better.
George Sand, (real name Lucile Aurore Dupin) was a 19th century French noblewoman and female example of this trope. Even while married, she took many lovers including Fryderyk Chopin, and was rumored to have a lesbian relationship with another woman. However, she was considered very unattractive by the standards of society at the time, and deliberately bucked the conventions for feminine dress and behavior, which were particularly strict for noblewomen. She wore men's cloths and smoked freely in public, both considered vulgar in the extreme for a woman. To quote one of her biggest criticsnote Charles Baudelaire at the time:
"She is stupid, heavy and garrulous. Her ideas on morals have the same depth of judgment and delicacy of feeling as those of janitresses and kept women.... The fact that there are men who could become enamoured of this slut is indeed a proof of the abasement of the men of this generation."
Ned Young, the man who famously slept through "The Mutiny on the Bounty". He was considered one of the least attractive men on board, but he was the most popular with the ladies.
, and the man looked like a troll doll you'd hang from the rear view mirror."
