"Gentlemen, I'm sure we can sort this out amicably. Look at it this way: if you could do what I could do, you'd do it too! But you can't. I can. And I have. And I'll do it again. So you should be happy for me, just a little tiny bit, don't you think?"
Miroku from InuYasha is The Charmer and is always flirting with women since his goal is having a child, his catchphrase being “Will you bear my children?”. While in the series is implied subtly that he has actually slept with several women, it is left to interpretation leaving it as an Urban Legend Love Life. That is until Word of Godcomfirmed it saying he used to have a 90% success rate with the ladies, but it went to zero after joining the team. It also didn’t help that he fell in love with Sango.
Guiche from Zero no Tsukaima. Possibly Julio as well, although he tends to have girls pursuing him.
Koon Eduan from Tower of God, father of Koon Aguero Agnis, has slept with so many women that he has the second largest amount of children in the whole Tower. There are so many, that in order to stop family feuds and succession wars, he has them perform in blood sports to establish a hierarchy.
Hol Horse has the same way with women, which he uses to take advantage of them - not in that way (at least, not that we're shown), but in order to use them to make his escape when needed.
Akio Ohtori and Touga Kiryuu from Revolutionary Girl Utena use, manipulate and abuse women and men alike using in great part their sex appeal for More than Mind Control effect. Then Akio does it to Touga, establishing him as a sort of Alpha Casanova.
Ruka Tsuchiya counts as well. He takes a Hands-On Approach with the female fencing club members, dates and beds Shiori, whom he later utterly humiliates, and is very forceful with Juri, despite the fact that he's supposedly trying to help her break free of her self-destructive cycle.
Aoshima in Ah! My Goddess, who is explicitly referred to as a "casanova." Fortunately, when he's not busy being a slimy excuse for a human being, he tends to be the Buttmonkey.
Paptimus Scirrocco from Zeta Gundam is a very evil version of this. He's basically what happens when you combine a Casanova with a Magnificent Bastard and give him the psychic powers of a Newtype. Generally the kind that uses his charms more to use woman as tools than just as sexual objects, though.
Explored to an extent in Golgo 13. The title character tends to have sex before a job, and does have good luck at getting women to join him in bed. However, he just as often hires prostitutes, and due to his notorious blank expression not changing, a number of readers have theorized he doesn't actually enjoy it.
Ryoji Kaji from Neon Genesis Evangelion is implied to be this. The only people he doesn't hit on are the underage ones (much to Asuka's chagrin), leading to the derogatory Fan Nickname "man-whore". That doesn't stop him from teasing Shinji about him living at Misato's.
Lord Aleister Chamber of Black Butler is implied to be this.
Agon of Eyeshield 21 has this trait tacked on to his already unpleasant personality. It's not especially relevant to the story, it's just another extension of his Jerk Jock personality and serves as yet another reason for the heroes to dislike him ("Down with guys who have girlfriends!").
He's also one of two characters that has luck with women in the entire series. The first one is Hatsujou None of the Nagas have any luck with women since they attend an all boys school, and Ikkyu and Yamabushi are very jealous.
Loki is a far more blatant example, until The Reveal and his return to the spirit world. When he thinks he's dying and starts withdrawing from everything, he's revealed to have had four girlfriends at once.
Different versions of Batman have either portrayed him as being with many women or as avoiding most women. A common feature to most versions is that he ends up alone.
His public persona as Bruce Wayne is one of these, constantly dating and breaking up with multiple women to keep up the Rich Idiot with No Day Job facade.
Jack from Fables and his spinoff comic Jack of Fables.
Also the entire point of Prince Charming. The reason he's in so many stories is because he constantly marries and abandons various princesses. This leads to him originally being less than popular in Fabletown.
Starfox of The Avengers. It's revealed in She-Hulk that he's an inadvertant rapist who unconsciously uses his psychic powers to get women into bed, but the canonicity of She-Hulk is sometimes dubious.
It's been firmly established what his powers are and how much control he has over them. She-Hulk just pointed out Unfortunate Implications that already existed.
In the case where Starfox was accuse of being a rapist in the same story it was revealed this was not true. He has not used his powers to get women. The woman who accused him did so to try and cover up the affair since she was a married woman.
For your consideration ladies and gentlemen, the Incredible Hercules. Pulls about as much tail as James Bond.
It should be noted with the above example that, contrary to the stereotype that Bond regularly kills the women he sleeps with (invoked by the "kiss kiss bang bang" catchphrase of the 1960s), in truth this has happened exactly three times in the history of the movie franchise ( Fiona in Thunderball, Fatima in Never Say Never Again, and the above example of Elektra in The World is Not Enough. And in the case of Fiona it's debatable whether Bond intentionally uses her as a human shield.).
He was apparently expelled from Eton after an "incident" with one of the maids...
Tony Stark in the Iron Man movie. Claims to have gone 12-for-13 in one year with Maxim cover girls (he couldn't make his schedule work with March, but December was twins). Seduces Christine Everhart, leaves her to wake up alone in his bed, and while showing Everhart the door, Stark's assistant Pepper Potts says that she's "taken out the trash" before.
A deleted scene set right before the Golmira scenes has Tony seducing and leading a woman off to bed... and picking up another in the hallway along the way. He then gives a lame excuse to bail on the apparently inebriated women. "I'm going to get ice for the champagne" or something like that. In the distance, we see Iron Man taking off.
Subverted in the movie and book Kiss The Girls where the kidnapping/rapist/murderer bad guy takes the alias "Casanova". After he drugs and attempts to murder one of his victims a character remarks "Yeah, he's cunning, but he doesn't know his history: The real Casanova would never have approved."
What's New Pussycat? stars Peter O'Toole as a man who just can't say no to women. He sees a psychiatrist to help him swear them off and be faithful to his fiancee, but the doctor is a deranged lech himself.
Shame presents a deconstruction. Brandon is a young handsome successful businessman who can easily pick up girls. But he's also a sex addict and will resort to prostitution and masturbation to satisfy his needs. And none of it ever gives him happiness.
Oscar Diggs, aka The Wizard of Oz, is one in Oz: The Great and Powerful. He's made his assistants, the strongman's wife ( really bad idea, that one), Theodora and Glinda fall in love with him.
Mr. Wednesday from American Gods is a lecherous old man with supernatural charm, a penchant for virgins, and no respect for age-of-consent laws. The book's protagonist, Shadow, reluctantly finds himself witnessing the seduction of a teenage waitress, deciding it was "like watching an old wolf stalking a fawn too young to know that if it did not run, and run now, it would wind up in a distant glade with its bones picked clean by the ravens." In fact, this is exactly how Shadow got conceived.
Casanunda the dwarf from Discworld is a parody of this trope.
But we can't really be sure, since he is also a self-proclaimed Outrageous Liar.
Well, it worked on Nanny Ogg. Of course, expressing a vague interest would work on Nanny Ogg...
The odds are that he's not lying about this one, at least. He's proven it to other women as well.
Anatole Kuragin from War and Peace. He's a well-known womanizer whose first interaction with a semi-main character is mademoiselle Bourienne, a maid at Prince Bolkonsky's house, while Anatole was there to court the prince's daughter Marya. He later marries the daughter of a Polish farmer in exchange for room and board during one military campaign, and then, just for fun, sets out to marry-and-kidnap Natasha Rostov.
Lude from House of Leaves, who actually keeps a list of his conquests, their prominent features, and how he had sex with them.
A character in ''Don Quixote' is also portrayed like this in the male villager's stories about her. We later find out these injuries were imagined, she was just being chaste and as she wisely points out, she can't help being beautiful.
Fictional comedian Monti Tree from My Screwups fit this trope to a T, losing his virginity at 13, to bedding supermodels well into adulthood. However that all comes to a complete stop when he finds out he had a son he didn't know about.
James Bond again. This is brought out most clearly in the last paragraph of the series, effectively describing how he can never settle down with one woman.
In the books it's a little more Byronic. For example, in Moonraker he expects to automatically be rewarded for his efforts by sex with Gala Brand, only for Brand to reveal that she wasn't kidding about being engaged.
In Dan Abnett's Gaunt's Ghosts novel Necropolis, Gaunt after a wartime fling thinks of his mentor Otkar who had left a trail of tearful women behind him and warned Gaunt not to get involved, as it would weaken him. Gaunt realizes that although as soon as the war is over, their social classes would separate them (which she knows too), he would now fight to the end to save this woman, and that his emotional investment in the Ghosts has in reality kept him on the job.
Larry Douglas in The Other Side of Midnight. The first "book" of the novel tells the life stories of two of his many conquests, Catherine Alexander and Noelle Page, via alternating chapters. The former marries him, unaware of his true nature; the latter, whom he abandoned years before he met Catherine, devotes her life to destroying him. The remainder of the story is about what happens when Noelle manipulates events to bring Larry back into her life.
Mr. Knightley fears Frank Churchill may be this in Emma, given the mixed signals he keeps sending both to Emma and Jane Fairfax. It turns out he's just an innocent if sometimes foolish Chick Magnet in a committed, Secret Relationship with Jane Fairfax.
Spyros Stavaronas, the attractive young shrimp fisherman in Alexandra by Scott O'Dell. At first, he uses his charms to distract Alexandra so his henchmen can smuggle cocaine on her boat. When Alexandra finds out, he further tries to seduce her into keeping his secret and not turning them into the cops.
Pretty common among the main male characters of the Sword of Truth series. Nathan Rahl, the prophet, often badgers the Sisters of the Light to send women to his rooms while he is in his Gilded Cage, and can often be seen with a woman on each arm after getting out. Zedd is implied to have interactions with several women over the course of the series. Richard himself, while more content to just have his one significant other, still manages to end up married to three different women and have several more who want him. The male villains are darker versions of this.
Although, as revealed in Mockingjay, this may actually be a subversion. He does love one single woman, Annie, and was forced into becoming a sex slave by the Capitol to protect her. His heartbreaker reputation is just the public front for what's really going on.
Jimmy (Snowman) in Oryx and Crake and The Year of the Flood by Margaret Atwood, is this and also a harbors a years-long romantic obsession with the same girl (then woman) as his sociopathic genius best friend, which leads to trouble
In a rare example of one in children's literature, The Roman Mysteries features Publius Pollus Felix, who is revealed as a Casanova in The Sirens of Surrentum.
Murillio of the Malazan Book of the Fallen specializes in seducing and bedding married women. He notes that all the students of the man who trained him in dueling ended up pursuing some vice; his was just a bit less dangerous. Ended up quitting after a younger woman seduced him and he nearly died when her suitor defended her "honor".
Apollo's Grove: Atollon, a priest of Apollo, at one point seduces a village woman using the same words his mentor had used to describe the sacred nature of Apollo's grove.
In On Fairy-Stories, J. R. R. Tolkien pointed out that first use of "faerie" in English was to refer to a Casanova, dressed up to seduce when he attended church. (The Fair Folk sort of faerie, not the little winged thing sort.)
Marcus of The Mark of the Lion begins the series as one; he is apparently quite skilled at seducing his family’s female servants with a mere glance, despite his string of girlfriends on the side.
You have to read between the lines in Lord Chesterfield's Letters to His Son, but it's there. "I repeat it again and again to you, Let the great book of the world be your principal study. 'Nocturna versate manu, versate diurna'; which may be rendered thus in English: Turn Over MEN BY DAY, AND WOMEN BY NIGHT. I mean only the best editions." (letter 137)
Menedemos in H. N. Turtletaub's Hellenic Traders series.
Aiden's very first scene in Of Fear and Faith ends with him convincing a woman who's angry at him for trespassing on her property to go to bed with him. He proceeds to charm almost every woman he meets from then on.
Patrick of Coupling behaves like a cold hearted seducer, unable to see women as anything but potential conquests, dumping his girlfriends almost immediately, and compiling a vast collection of sex tapes of his conquests. Interestingly, he avoids being loathsome, as he's portrayed as stupid rather than deliberately malicious.
Barney from How I Met Your Mother. There's barely been an episode in the series where he hasn't hit on at least one woman, and uses a number of bizarre means to seduce them (which are surprisingly successful).
Slightly deconstructed — for the most part, he only does well with bimbos and desperate women.
Ted: Does that ever work for you? (referring to one of Barney's numerous pick up lines and schemes)
Barney: Ted, the question is do they ever not work for me? Either way the answer is about half the time.
In a recent episode Barney was revealed to have slept with 200 women (and counting). Marshall, while disgusted, decided to crunch the numbers based on the number of women Barney hits on on average every week and calculated (albeit with quite a bit of leeway) that based on that information and his years of sexual activity, Barney's success rate with women works out at a little over 1%. There's no telling if that is anywhere near accurate though.
It varies from season to season. In one episode he successfully nails seven different girls in seven days, most of whom leave the bar with him within seconds of being hit on.
In season 7, it is revealed that he will be married soon. Season 8 has him propose to the woman (after having proposed to someone else in season 7) he will marry.
Kramer claims to be this, and while he actually has fewer girlfriends than either of them, the ones he DOES get tend to be better and theoretically harder to attain. See: Uma Thurman, nuns, lesbians, Elle MacPhearson. See also Kavorka Man.
Latka's alter ego Vic Ferrari from Taxi, introduced at the end of Season 3 and the catalyst for a Split Personality problem that unfolded over much of the following season. This climaxed when he had to win back his old girlfriend Simka from Vic (whom he referred to as "a two-bit bossa nova"). Once he managed to convince her that Vic wouldn't actually love her, she was able to convince Vic to leave for good.
Bulldog: [on the phone] Come on now. No tears. I'll never forget you either, Sandy. Linda? Really? I thought I was talking to your sister. Oh well, tell her same goes.
Roz Doyle was always played as a female version of this trope in particular, rather than just Really Gets Around. While the characters often cracked jokes about her promiscuity, they nearly always implied a predatory and perpetually lustful person who loved the chase and would jump through ridiculous hoops (including construct elaborate lies and hook her friends into facilitating hook-ups) in order to get laid, rather than misogynistic jokes indicative of a cheap slut, as would be expected in a comedy featuring a promiscuous woman. Also, Roz was always portrayed in a far better light than Bulldog because while Roz would sleep with loads of guys, she also had very clear standards that she rarely compromised (which is perhaps the reason her dates were so often men who required her to come up with hilarious schemes in order to get them to put out).
Al Mundy of It Takes a Thief (1968) seems to pick up a new woman every episode, and even the ones who are initially frosty are charmed by him in the end. He doesn't seem to get much actual sex, though, because Noah always puts a stop to things just when the woman is softening up.
An episode of The Equalizer had a handsome chronic womaniser get kidnapped by industrial spies who keep insisting that "she said she gave it to you" and refuse to believe his claims of innocence. Realising he's going to be tortured he quickly "confesses" and promises to get "it" to them in 24 hours — he then has to hire the Equalizer to help him sort though the multitude of women he's dated to find the right one. "It" turns out to be a microdot on a matchbook handed to him with a girl's phone number written on the inside.
Before Nathan of One Tree Hill fell in love with Haley, he was most definitely one of these, even if he was taken at the time. Haley is not happy when, in Season 4, after they are married and pregnant, she finds out that Nathan made a sex tape with their friend Brooke (though it was before he even knew her).
Nathan: You want me to write a list of every single girl I've ever... Haley: No, no, I guess not every single girl. You can cross Peyton, Brooke, and my sister off of that list. Nathan: You really think that's a good idea? Haley: Yes! And here. I'll make it easy for you. Take the phone book and just cross off the name of every girl you haven't been with.
Sam Axe of Burn Notice seems to make his living "sponging off every rich divorcee in the greater Miami area."
This brings in an Evil Counterpart when they meet Charles, a womanizer who manages to seduce rich women into revealing their bank codes and bleed them dry. In comparison, Sam just finds himself a sugar-momma and provides genuine affection, company and is monogamous.
Played with (as with pretty much every spy trope) on Chuck. On several occasions Chuck is asked to pretend to be this, even though he's very much not. Outright parodied with Seduction School expert Roan Montgomery (another John Larroquette role). Despite his methods often being played for laughs, they still work.
On the backglass art for Eight Ball, even as "the Fonz" playing pool with his girl, a waitress in the background is hungrily eyeing him.
Ma Ha Suchi from Exalted was one of these in the First Age. Every character in Exalted has a guiding Motivation. His was, "Sleep with every Celestial Exalted in Creation." It didn't hurt that he was ridiculouslyBishōnen. Then the Wyld happened to him...
One of the major traits of Elminster Aumar of Shadowdale, the great archwizard from the Forgotten Realms setting, is that he'll flirt and/or sleep with just about anything that has two X chromosomes and isn't related to him. Just in his own novel series he's bedded humans, elves, a lich, several avatars of a goddess, and a song dragon in human form (and he sired a daughter with that one). The only thing keeping him out of Extreme Omnisexual is that he's straight.
Cowboy Casanova, by Carrie Underwood.
He's a good time, a cowboy casanova leaning up against the record machine, Looks like a cool drink of water but he's candy-coated misery. He's a devil in disguise, a snake with blue eyes and he only comes out at night, Gives you feelings that you don't wanna fight, you better run for your life.
In Spring Awakening, handsome, creepy, and arrogant Hanschen Rilow is mostly played for laughs, though it's a little sad when he seduces his classmate Ernst. The scene they share is tragically unbalanced, given all the power Hanschen has over Ernst:
Ernst: I love you, Hanscen, as I have never loved anyone. Hanschen: And so you should.
Even older than the original Casanova was the character Don Juan, whose first recorded appearance was in the 17th century Spanish play The Trickster of Seville and the Stone Guest.
Don Juan was the subject of Mozart's opera Don Giovanni (of which we see an excerpt, and a vaudeville parody, in Amadeus).
In psychology, a person who displays a need to dominate and have multiple sexual relationships with woman is said to have Don Juanism.
Into the Woods has an amazing parody of this in the songs 'Agony' and the reprise by the two princes.
The Duke in Rigoletto certainly qualifies, and is a Karma Houdini to boot.
Willmore from The Rover by Aphra Behn is definitely this,his name literally means 'Wills for more sex',and he comes complete with Karma Houdini
"Dear Van De Graff bride, I must make love to you, and transport you to the place of ecstacy. Sooner is better than later. Signed, Aldolpho."
Panther Caruso from Star Fox relentlessly pursues Krystal, and is described more than once by Nintendo as being a self-proclaimed ladies' man. He could, however, be a slight subversion in the sense that he never really gets anywhere with Krystal (who shares a mutual affection with Fox McCloud), whom tends to either ignore, humour or outright reject his advances in Assault and their cameo appearances in Super Smash Bros. Brawl. The only game where he does seem to succeed in any way with her is Command, and whilst he is depicted as devoted to her, it's very much implied the only reason she's with him is because Fox kicked her off the Star Fox team (for her own safety, though she didn't take it that way) and that she joined Star Wolf as a means to get backat him rather than falling for Panther's charms. That, and Command seems to be a case of Canon Discontinuity if the current status quo is any indication.
Gannayev of Neverwinter Nights 2: Mask of the Betrayer regularly abuses his Spirit Shaman powers for the sake of jumping into the fantasies of innocent young farmgirls and having hot dream-sex, although most of his exploits occurred prior to the plot.
Goto, from Mana Khemia 2, is seen going on dates with various students in groups (as well as some one on one time with the Chairman). When the main cast doubt his claims of natural desirability they take a school-wide poll, only to find out that 100% of the girls want him as well as 1/3 of the guys, and the only reason the members of Ulrika's workshop aren't effected is he's purposefully toning down his charm around them. Then things get a bit complicated when the son of one of his old flings shows up looking for revenge...
To some extent, the protagonists in Persona 3 and Persona 4 can be this, depending on the player's decisions. If you're dating more than one girl and they discover what's happening, chances are you'll have to deal with some VERY pissed off girls and generally put the situation right. This is less so in Persona 4 where you won't be penalised as much, but you can still date/flirt with nearly every girl in the game (except for Hanako and Nanako, thankfully), AND you even get called an emotional heartbreaker during the cross-dressing pageant:
MC/Presenter: "She" has made more girls cry than there are stars in the sky! Presenting our transfer student who's been breaking hearts in the second year Class 2, character name!
Assassin's Creed II has beat-up missions, which usually revolve around a woman looking for a random dude to beat up their cheating bastard husband. Hilarity Ensues when they are caught with their lovers, then beaten the shit out of.
You also meet Casanova himself who has you deliver love letters to two women at the same time.
Plus Ezio himself, who gets compliments from every woman in Italy.
In the Lair of the Shadow Broker DLC for Mass Effect 2, The Illusive Man is revealed to have slept with six Playboy-caliber women in the past week. One of them came back for seconds.
Zelos Wilder from Tales of Symphonia. Yeah he doesn't get anywhere with Tsundere Sheena, but any other woman in the game he addresses IMMEDIATELY fawns over him.
At the beginning of The Sims 2, Don Lothario is engaged to Cassandra Goth, despite having a total of four lovers simultaneously.
Any Romance Sim, for that matter.
Diablo: The second game indicates that Deckard Cain was this in his youth. He says about Anya being like some Zakarum priestesses he had known. He also says that they did not have to take vows of chastity. Do the math.
Makoto from School Days is flanderized into this about halfway into the story. In the anime and at least one game ending, this comes back to bite him in the ass when he is murdered by one of his spurned lovers.
Really, the anime version acts a deconstruction of the more malicious version of this trope: Makoto is skilled at bedding women almost to the point of straining credibility enough to push him into Kavorka Man territory considering his (not outstanding) looks and Jerk Ass attitude, but this shouldn't obscure the fact that when it comes to anything deeper and more lasting than this, Makoto is an absolute idiot who doesn't understand the female heart at all, and indeed only turns to his life of serial affairs because he was too impatient and thick-headed to win the heart of the girl he had a crush on in the first place.
Itsuki in SHUFFLE! and Tick Tack'' is pretty much always seen failing when he flirts with girls, but he's actually pretty popular. He has no known true relationships and it's hinted that he's actually in love with his friend Mayumi.
Adam Terrence from the webcomic Loserz. As seen here.
Vlad, the Make-Out King, from Achewood. (Or so he claims)
Joe Rosenthal in It's Walky! takes this to the point of practically being another super-power: he managed to have sex with an astonishing 2030+ women before settling down with Rachel. This is all the more astonishing given his somewhat kavorka-ish horndog attitude: one time, he set out intentionally to sleep with 30 women in one day (to 'get the gay off of me' after having his head shoved in Walky's crotch in an attempt to obscure his face), and succeeded.
While he stands out, he is hardly the only Abductee who is highly successful in bed, either - which is rather ominous given that the Aliens and Linda Walkerton apparently meant to breed the Abductees to make the next generation of their Super Soldier army.
El Chupecabre ("Chuy") from Girly is irresistably attractive to women. He took this as his calling and left a string of naked, immensely-satisfied women in his wake until Winter and Otra helped him to mend his ways.
Zach, of Girls with Slingshots is arguably a subversion. Sure, he's slept with hundreds of women, but he sees it as a community service thing. He gives virgins a good first time and helps service the elderly to make them feel loved again.
Zii from Ménage à 3 has a borderline superpower to seduce (presumably) straight women into sleeping with her and is pretty much single-handedly responsible for everyone being bi. The only girl she's tried and failed to get with so far is DiDi, but Zii still managed to convince her that she might be bi as well. Of course, Zii has also slept with a lot of men as well, but it's not exactly difficult to do that.
Thomas the bard from Yet Another Fantasy Gamer Comic is such a master at the game of love that he can have any woman he wants, even one who wants to clobber him. Take this comic for example, in which he demonstrates his prowess to Clover the halfling. He tips a waitress by flicking a coin into her cleavage, causing it to fall through the bottom of her dress and roll away. As she bends down to pick it up he smacks her on the rear. She understandably prepares to kick his ass, but he whispers something in her ear that has her making out with him immediately afterward. All Clover can say after witnessing this is "Wow... you're good."
Nolan from Regular Guy: Women seem to find his beard irresistible, and he had his "thingy" declared a work of art. He's pretty modest about it, though.
Ted from Greg, is constantly the target of women's scorned hatred. While he is not avoiding ex-lovers, he is seeking out new women to love and leave.
Don Sebastiano, at the Super Hero School Whateley Academy in the Whateley Universe. The Don (as he is also known) is a major campus supervillain, and enjoys romancing women. Once he's gotten what he's after he likes to dump them with as much public humiliation as he can arrange. He seems to enjoy the 'hurting them' part more than the 'boinking them' part, which makes this more like a Kavorka Man activity.
Hugh Griffin, president of the *USA in Decades of Darkness. As the author writes, his wife knows when to look away.
Boomhauer from King of the Hill. Despite the fact that most of his conquests don't seem to mind, he gets a cruel comeuppance when the tables are turned on him: the one woman who he does fall in love with turns out to not even be able to get his name right, and tells him, to his face, in the arms of another man, while he's on his knees after proposing to her, that whenever he talks, she just nods and smiles until his pants come off. Ouch.
Mayor Joe Quimby from The Simpsons, who is an exaggerated, evil-mirror-universe parody of Edward F. Kennedy.
Glenn Quagmire from Family Guy. He is a step forward from being just a regular Casanova - he is a pervert, victimizer, and a rapist as well.
Anthony Quinn. Three marriages, ten legitimate children, three acknowledged illegitimate children, and a string of acknowledged and confirmed sexual conquests stretching across four continents.
Errol Flynn. He was such an accomplished and charming seducer that when he got into legal trouble in the early 1940's about having an affair with a teenager, he not only charmed the mostly-female jury into acquitting him, but ended up marrying the L.A. country sheriff's daughter, who was running a concession stand in the courthouse during the trial. The slang expression "in like Flynn" reportedly was coined as a result of that particular scandal. (This may also be an expression of Values Dissonance, in that Flynn would probably have had his career wrecked today, charm or no charm.)
David Niven, in one of his autobiographies, recounts a practical joke he and a couple of Flynn's other buddies once pulled. They hired a beautiful young prostitute to play the role of an innocent teenager. Just as Flynn was about to consummate his seduction of the girl, another sexy streetwalker, playing the girl's aunt, walked in. Much Hilarity Ensued as the other woman roundly scolded both Flynn and the girl and ordered her "niece" out of the room. When the girl had left, the older woman asked Flynn, "Do you know why I did that?" Errol said no, and the woman said, "Well, Mr. Flynn, it's because...I wanted some of that myself!!" and jumped him.
Screamin' Jay Hawkins estimated he had about 57 children by different women— and the number could have in fact been as high as 75 (!!!).
Gene Simmons of KISS fame, who has the pictures to prove it. Though his claims are still probably exaggerated. In fact, could be applied to many rock stars to some degree.
One is well-advised to take some of his wilder claims with a grain of salt, since he's been "happily unmarried" to former Playboy playmate Shannon Tweed for over 2 decades and has had two children with her. Then again, his reputation certainly doesn't seem to bother her all that much...
Wilt Chamberlain famously claimed to have slept with "20,000 women" in his autobiography. This, however, is all but disbelieved by anyone with a brain. Dennis Rodman, no paragon of monogamy himself, wrote: "Wilt Chamberlain lied out of his ass and made some money. He said he slept with 20,000 women. Think about it. That's three or four women a day every day for fifteen to twenty years. I defy anyone to keep up that kind of pace."
Cracked's calculations are a little different, but no less unlikely.
Hugh Hefner. Interestingly, despite his reputation, he was a late bloomer, and did not lose his virginity until he was 22 years old.
Anthony Kiedis of Red Hot Chili Peppers is infamous for this, in his book Scar Tissue it appears he is with a different girl in every chapter or so. However, he averts this trope somewhat in that he only has one child who was born fairly recently.
Bryan Ferry likes to cultivate this image both in his music and in real life. He has regularly been in relationships with women considerably younger than him (in one case, 35 Years younger). He was however happily married for 21 years (from 1982 to 2003) and had several children, ironically his wife wanted the divorce because she was having an affair herself.
There is a story that during World War II, Stalin received a report about one of the military commanders (usually stated to be Rokossovsky) being that, and was asked "What shall we do"? His answer? "We shall envy"!
Stalin himself was that, at least in his younger years. Probably explains his attitude to the above.
Clint Eastwood. Seriously, just look at his Other Wiki entry. To quote: Eastwood told biographer Richard Schickel that he lost his virginity at age 14. He has fathered at least seven children by five different women and been described as a "serial womanizer". According to biographers Marc Eliot and Patrick Mc Gilligan, Eastwood always had a strong sexual appetite and had many affairs with women through the years, including actresses Catherine Deneuve, Jean Seberg, Peggy Lipton, Kay Lenz, Jamie Rose, Inger Stevens, Jo Ann Harris, Jane Brolin, Jill Banner, script analyst Megan Rose, and swimming champion Anita Lhoest. Biographers claim he has also fathered at least four children that have been aborted, and another who was given up for adoption in 1953. Biographers and friend Paul Lippman have claimed that Eastwood was particularly sexually active and promiscuous in the 1970s and that he used his apartment close to the Hog's Breath Inn which he purchased in Carmel in the early 1970s to meet young ladies for "nooners" and "five in the afternooners". According to Lippman, "Eastwood seemed to get a bang out of this kinkier side to himself and rarely concealed it, often gloated about it".
Neil Strauss wrote a book about it. See Literature.
Chico Marx was known by his friends (and fellow Marx brothers) for his uncanny ability to attract women. According to one anecdote, he could wink at a lady in the car next to him at a red light, and within ten minutes they'd be in a hotel room together. (In fact, his name is actually pronounced "Chick-o", due to the fact that he was a "chick-chaser").
Cao Cao could count as this. 25 sons from different women, and unknown number for daughter. No less than 14 wives (or concubines).
By way of explanation: Franklin was a notorious womanizer throughout his life. As a young man, he was smart, handsome, charming, and buff (printers back then carried large cases of heavy lead type all the time, plus Franklin was fond of swimming), which naturally made him a hit with the ladies (to the point that he identified it as his biggest vice); after he opened his print shop, he could add "successful" to that list. As an older man, he was rich and famous, which helped him keep the ladies even as his looks went away and his physique turned from chiseled to double-chinned.note As an illustration, when a French lady asked Franklin about his flab, "What would you say if that was on a woman?", the septuagenerian Franklin said, "My lady, twenty minutes ago, that was on a woman". His skill at seduction—both literal and figurative—probably helped in getting France to make a firm alliance with the US during the American Revolution.
If Real Life was fiction, than Prince Felix zu Schwarzenberg would be a very dark take on this trope, possibly verging on deconstruction. A major ladies man in his younger days, Felix slept, drugged, and drank his way across every major court in Europe, and scored with some of the most sought after women of the time period. And by the time he was forty, he was so burned out that people who knew him said that there was nothing left, save cold, icy ambition (for his country, not himself). Becoming Foreign-Minister of Austria in 1848, Felix served as advisor and mentor to Emperor Franz-Josef advocating a pragmatic, cynical foreign policy based on what was best for Austria. When asked if Franz-Josef should show mercy to the rebels of 1848, Felix responded that "Mercy is a fine quality, but first, we must have some hangings." He later stated that Austria would "shock the world by the depth of its ingratitude." He died prematurely in 1852 of a stroke, mourned in Austria, and hated everywhere else. In London, his duplicity and his womanising actually earned him the nickname "The Prince of Cadland."
Felix reportedly got a woman pregnant, than proceeded to end the affair and inform her husband of what had occured, getting her thrown out in the street. The woman in question was well-known for her inability to keep her legs closed (she was in fact famous in the tabloids for sleeping around), but Felix's behaviour was so callous that the press actually sided with her.