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[[quoteright:350:[[Pinball/PlayboyBally https://static.tvtropes.org/pmwiki/pub/images/hef.png]]]]
[[caption-width-right:350:Hugh Hefner knows how to accessorize.]]
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You know him. The fabulously wealthy guy, who rubs shoulders with the rich and famous, the movers and shakers of industry, and may even have connections in the political arena. The one sitting on top of more capital than most people can imagine and more than they themselves will ever be able to spend in a lifetime. Add dashing good looks, boyish charm, [[SharpDressedMan swank tailored suits]], lavish living in a downtown penthouse loft and a countryside mansion, [[WealthyYachtOwner a huge yacht]], luxury cars, hanging out in VIP-only lounges in nightclubs, and weekend excursions on the Rio Grande or the Virgin Islands and it's no wonder they're regarded as part of the "jet set".

The combination of wealth, power, and charisma [[GoldDigger draws women to them]] ''[[ChickMagnet in droves]]'' -- and he ''exults'' in it, because he can have his pick among supermodels and starlets. Even if he's the type to [[TheCasanova love 'em and leave 'em]], he knows there'll always be another to take their place, ensuring you'll never get [[ThePornomancer as much action as he does]]. He is TheHedonist, so there may be a bevy of live-in girlfriends and mistresses.

The classic suit is the smoking jacket. Their [[BillionaireWristband luxury accessories aim to impress]]. If they light a cigarette, it's with an engraved platinum lighter. If they sign for a huge suite at a luxury hotel, it's with a silver Cartier fountain pen. They wear a Philippe Patek or Tag Heuer watch. For this reason, live action shows featuring playboys are great works for luxury ProductPlacement. When relaxing at home, silk pajamas and a robe are the favorite garb.

In addition to wealth and a glamorous personal style, playboys are cosmopolitan and well-read. They can discuss the novels of Norman Mailer, and Kurt Vonnegut, chat about Nietzche's philosophy or Picasso's painting style, favorite stagings of ''Theatre/LaBoheme'', and debate political issues.[[note]]"Hugh Hefner, Iconic Playboy, Dies at 91" in ''Vanity Fair''. By Donald Liebenson, September 27, 2017.[[/note]] The playboy has a well-rounded education, which allows them to be at ease conversing with everyone with from authors and artists to [=CEOs=] and heads of state.

Playboys are also [[ManOfWealthAndTaste gourmands with a refined palate]]. Their [[WineIsClassy wine cellar]] and [[LuxuriousLiquor liquor cabinet includes rare, imported bottles]]. Their drink of choice is an elegant cocktail. [[DistinguishedGentlemansPipe Pipes]] and fine cigars are also appreciated.[[note]]The lead illustration depicts Hugh Hefner with his iconic pipe.[[/note]]

Favorite [[SnobbyHobbies playboy hobbies]] include gambling at elite casinos (Blackjack, roulette, etc); hanging out with business elite at [[SmokyGentlemensClub wood-paneled private club]]; gala, black tie ClassicalMusic events; art openings at fancy galleries; auction houses for fine art; posh equestrian events and other SnootySports; and luxury travel in their private jet to glamorous and exotic locations (French Riviera, Paris, Rome, tropical beaches).

In spy thrillers and heist films, they may be part of a CaperCrew. Usually as [[TheTeamBenefactor the one covering the group's expenses]], and just as likely to [[ScrewTheRulesIHaveConnections use their connections]] to bail the team out of a tight spot, should it become necessary.

Ones with fighting skills are likely to be [[CulturedBadass Cultured Badasses]]. For villainous examples see ManOfWealthAndTaste.

Spear counterpart to the {{Socialite}}.

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!!Examples:
[[foldercontrol]]

[[folder:Advertising]]
* "Advertising/TheMostInterestingManInTheWorld" series of advertisements for Dos Equis beer centers around a yet-unnamed older gentleman who has no shortage of interesting tales about his life. He also appears to be quite wealthy and is always surrounded by beautiful women.
[[/folder]]

[[folder:Anime & Manga]]
* Roger Smith from the anime ''Anime/TheBigO'' is a heroic millionaire who protects people with his giant robot.
* Ukyo from ''Anime/SamuraiSeven'' could be seen as a variation of this, considering his extensive harem and insane amounts of wealth (the room all his harem girls gather in has a ''whale in a tank'').
* Ranmaru Mori from ''Manga/TheWallflower'' fits this trope very well.
* In ''Manga/TokyoGhoul'', Tsukiyama's grandfather was apparently an infamous womanizer. His father worried he would turn out the same as a result of his SchoolIdol status, but this turns out to be an unfounded concern.
[[/folder]]

[[folder:Comic Strips]]
* In ''ComicStrip/CalvinAndHobbes'', "Six-year old millionaire playboy Calvin" is the SecretIdentity of Calvin's superhero alter ego, Stupendous Man.
[[/folder]]

[[folder:Comic Books]]
* [[Franchise/{{Batman}} Bruce Wayne]] acts like this in some continuities. During the No Man's Land arc, he pretends to be sunbathing with hot chicks on a beach during a voice call to Lucas, with Oracle providing real-time giggling and noise effects. Batman, in costume, even adopts his "careless playboy" body language.
* Post-''Crisis'' Lex Luthor is a villainous example. Some writers have him actually ''preferring'' that the women are only attracted to his money and influence. It's a turn-on for him that he's a turn-off for them.
* ''ComicBook/GreenArrow''
** Oliver Queen, before he gave away his fortune in the Seventies. The girls, the wining and dining and partying. Then he started dating Black Canary and founded a center for troubled youth.
** Averted on round two: After the events of "Quiver", when Stanley transferred all his considerable funds to Queen's name [[spoiler:because he expected to take over his body]], Green Arrow didn't go back to being a playboy; he wanted to try to patch things up with Black Canary, and he had a new sidekick to care for.
* [[ComicBook/IronMan Tony Stark]], especially in [[Film/IronMan the movies]].
** [[ComicBook/UltimateMarvel Ultimate Tony Stark]] takes this to somewhat ridiculous degrees.
[[/folder]]

[[folder:Fan Works]]
* Billionaire Neptune in ''Fanfic/RoadsideAssistance'' is married to Weiss but he gives off the persona of a womanizer nevertheless. In actuality, it's just for show and he's gay (and [[TheBeard so is his wife]]).
[[/folder]]

[[folder:Films -- Live-Action]]
* Subverted in ''Film/TheLover'' where The Girl's eponymous lover is a handsome and wealthy Asian hedonist, but is physically weak and lacking in self-confidence.
* Creator/TomCruise's character in ''Film/VanillaSky''.
* Franchise/MarvelCinematicUniverse:
** Tony Stark is this and revels in it. After his change of heart, though, he starts trying to behave better. Key word being "try".
** Creator/StanLee is hinted to be one in his ''Film/IronMan1'' cameo.
* Bruce Wayne in ''Film/BatmanBegins'' pretends to be one as part of his IdleRich guise, but only as a distraction to provide cover for his Batman SecretIdentity. It wasn't played up in subsequent films, as the point had cinematically been made.
* Derek Flint in '' Film/OurManFlint'' could be the codifier.
** Penthouse? Check.
** Private jet? Check.
** Bevy of beauties at his beck and call? Check, Check. Check! And CHECK!! (He was up to five at one point, but by the sequel, ''Film/InLikeFlint'', he was 'trying to cut down' and had only three (live in, anyway).
[[/folder]]

[[folder:Literature]]
* Tsu Ma in David Wingrove's ''Literature/ChungKuo'' series. It helps being the supreme lord of West Asia.
* Deconstructed in ''Literature/TheGreatGatsby'' with Gatsby himself.
* In ''Literature/TheFleaPalace'' by Creator/ElifShafak, Edith is somewhere between this and a KavorkaMan (a RareFemaleExample in either case). She uses her wealth and taste to welcome a crowd of men to her house (prefers intellectuals) and they're fascinated and want to sleep with her although she's ''extraordinarily'' ugly.
[[/folder]]

[[folder:Live-Action TV]]
* Kang Hyun-min from ''Series/CinderellaAndTheFourKnights'' was raised to be heir to the fantastically wealthy Haneul ''chaebol''. He throws money and luxuries around without a care in the world and has a new girlfriend every week.
* Zack Young tried to emulate this kind of character during the third season of ''Series/DesperateHousewives''.
* Chuck Bass from ''Series/GossipGirl''.
* ''Series/{{Smallville}}''[='=]s Lex Luthor, although the playboy part is more reputation.
* Amos Burke on ''Series/BurkesLaw''.
* ''Series/{{Arrow}}''. Oliver Queen along with his RomanticWingman Tommy Merlyn.
-->'''Tommy:''' There's this girl that I'm interested in. And I am really not sure how to pursue it.
-->'''Thea:''' Have you tried using your usual lines? Hi, my name is Tommy Merlyn and I'm a billionaire, but I don't look like Warren Buffet.
* Julian from ''Series/{{Deception|2013}}''.
* Series/{{Castle|2009}} is introduced as one at the beginning of the show.
* ''Series/DowntonAbbey'': Harold Levinson, Cora's brother, is "rich as Croesus" (in his niece Mary's words) and fond of "pretty girls" (in his own words). He [[ChivalrousPervert does have some rules]], though.
[[/folder]]

[[folder:Video Games]]
%%* ''VideoGame/TalesOfSymphonia'''s Zelos Wilder
* Devin Weston from ''VideoGame/GrandTheftAutoV'', who frequently brags about his sexual conquests on the in-game social networking sites.
* Lorne de Havilland, one of Agent 47's targets in ''VideoGame/HitmanBloodMoney''. In addition to publishing a very Playboy-esque magazine, Lorne owns a series of strip clubs. His clubs have hidden cameras in them, and he uses the footage to blackmail famous patrons.
[[/folder]]

[[folder:Visual Novels]]
* ''VisualNovel/UminekoWhenTheyCry'' has Battler and Ange's father Rudolf Ushiromiya, known for being an extremely shrewd businessman (bordering on CorruptCorporateExecutive) ''and'' a legendary womanizer. His second wife ''and'' business partner, Kyrie, has... [[YanDere some issues]] about it.
[[/folder]]

[[folder:Western Animation]]
* Xander Crews from the show ''WesternAnimation/FriskyDingo'' acts as the super hero Awesome X. He killed all of the bad guys in the town but it is hard to consider him heroic as he is an asshole.
[[/folder]]

[[folder:Real Life]]
* Hugh Hefner was one, as reflected in the name of [[Magazine/{{Playboy}} the magazine he founded]]. As such, he is the trope namer, in addition to being an iconic example of the luxurious, hedonistic lifestyle.
* [[http://en.wikipedia.org/wiki/Porfirio_Rubirosa Porfirio Rubirosa]] had been one: five times married, former son in law of [[Literature/TheFeastOfTheGoat Rafael Trujillo]], [[InvertedTrope inverted the trope]] by becoming millionaire ''because'' [[TheCasanova of his talent with ladies]], had a brilliant career [[{{Ambadassador}} as a diplomat]], was a great racing driver and airplane pilot. (Unfortunately for him, he died by crashing in a Ferrari.)
* Actor George Clooney has a reputation for being one of these.
-->'''Kevin Smith:''' See, George Clooney doesn't fucking give a shit [if his movies bomb]. He would just be like, "They didn't like it? Fuck it." (''mimicks getting head from a woman''). Or it'd be like (''counting stacks of bills'') "10 million!".
* Donald Trump ''used'' to have this reputation when the media documented his private life before he ran for office (married several times, dated pornstars, owned a beauty pageant), but proved to be such a unique character that he spawned [[{{Trumplica}} an entirely new trope]].
[[/folder]]
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