History Main / MillionairePlayboy

* Julian from {{Deception}}.

You know him. The suave millionaire who surrounds himself with beautiful women. Yes, they're only attracted to his money and influence-- but he ''knows'' it. He ''exults'' in it. And you're never, ever, ''ever'' going to [[TheCasanova get as much tail as him]].

* The "Most Interesting Man in the World" 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.

* In 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".

* [[Radio/TheShadow Lamont Cranston]].

* ''VideoGame/TalesOfSymphonia'''s Zelos Wilder

* Hugh Hefner is one, as reflected in the name of [[Magazine/{{Playboy}} the magazine he founded]].

* Deconstructed in ''TheGreatGatsby'' with Gatsby himself.

** [[UltimateMarvel Ultimate Tony Stark]] takes this to somewhat ridiculous degrees.

* Xander Crews from the show ''FriskyDingo'' acts as the super hero Awesome X. Xander is also a RichIdiotWithNoDayJob. He killed all of the bad guys in the town but it is hard to consider him heroic as he is an asshole.

* [[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 [[HoistByHisOwnPetard appropriately]], by crashing in a Ferrari.)
* Actor George Clooney has a reputation for being one of these.

* [[GreenArrow Oliver Queen]], before he gave away his fortune in the Seventies.

* Ranmaru Mori from ''TheWallflower'' fits this trope very well.

* Lorne de Havilland, one of Agent 47's targets in ''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.

* Ukyo from ''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'').

* Actor George Clooney has a reputation for being one of these. In 2007 he stated that he will never marry again (he had been married once before from 1989 to 1993). And his relationship history includes several beautiful actresses and models.

* Lorne de Havilland, one of Agent 47's targets from ''HitmanBloodMoney''. In addition to publishing a very Playboy-esque magazine, he owns a series of strip clubs. His clubs have hidden cameras in them, and Lorne uses the footage to blackmail famous patrons.

* TomCruise's character in ''VanillaSky''.

** Creator/StanLee is hinted to be one in his ''Film/IronMan'' cameo.

* {{Smallville}}'s Lex Luthor while the playboy part is more reputation.

* Zack Young tried to emulate this kind of character during the third season of ''DesperateHousewives''.
* Chuck Bass from ''GossipGirl''.

* Oliver Queen in "Series/{{Arrow}}".

* {{Castle}} is introduced as one at the beginning of the show.

* Tsu Ma in David Wingrove's ''ChungKuo'' series. It helps being the supreme lord of West Asia.

You know him. The suave millionaire who surrounds himself with beautiful women. Yes, they're only attracted to his money and influence-- but he ''knows'' it. He ''exults'' in it. And you're never, ever, ''ever'' going to [[TheCasanova get as much tail as him]].

[[folder: Real Life ]]

* Hugh Hefner is one, as reflected in the name of [[Magazine/{{Playboy}} the magazine he founded]].
* [[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 [[HoistByHisOwnPetard appropriately]], by crashing in a Ferrari.)

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* [[TheWallflower Ranmaru Mori]] fits this trope very well.

* [[{{Batman}} Bruce Wayne]] acts like this in some continuities.

* [[TheShadow Lamont Cranston]].