Main/Millionaire Playboy - Television Tropes & Idioms

Hugh Hefner knows how to accessorize.

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 get as much tail as him.

If he is moonlighting as a superhero, see Rich Idiot with No Day Job.

Examples:

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Advertising

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.

Anime and Manga

Roger Smith from the anime The Big O is a heroic millionaire who protects people with his giant robot. He also averts Rich Idiot with No Day Job, as he has an extremely difficult, high-profile and well-paying day job as a negotiator that funds Big O's upkeep, even.
Ukyo from Samurai 7 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 The Wallflower fits this trope very well.

Comic Books

Bruce Wayne acts like this in some continuities.
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.
Oliver Queen, before he gave away his fortune in the Seventies.
Tony Stark, especially in the movies.
- Ultimate Tony Stark takes this to somewhat ridiculous degrees.

Film

Tom Cruise's character in Vanilla Sky.
In Marvel Cinematic Universe, Tony Stark is this and revels in it. After his change of heart, though, he starts trying to behave better. Key word being "try".
- Stan Lee is hinted to be one in his Iron Man 1 cameo.

Literature

Tsu Ma in David Wingrove's Chung Kuo series. It helps being the supreme lord of West Asia.
Lamont Cranston.
Deconstructed in The Great Gatsby with Gatsby himself.
In The Flea Palace by Elif Shafak, Edith is somewhere between this and a Kavorka Man (a Rare Female Example 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.

Live-Action TV

Zack Young tried to emulate this kind of character during the third season of Desperate Housewives.
Chuck Bass from Gossip Girl.
Smallville's Lex Luthor, although the playboy part is more reputation.
Amos Burke on Burkes Law.
Oliver Queen in Arrow.
Julian from Deception.
Castle is introduced as one at the beginning of the show.
Downton Abbey: 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 does have some rules, though.

Video Games

Tales of Symphonia's Zelos Wilder
Devin Weston from Grand Theft Auto V, who frequently brags about his sexual conquests on the in-game social networking sites.

Western Animation

Xander Crews from the show Frisky Dingo acts as the super hero Awesome X. Xander is also a Rich Idiot with No Day Job. He killed all of the bad guys in the town but it is hard to consider him heroic as he is an asshole.

Real Life

Hugh Hefner is one, as reflected in the name of the magazine he founded.
Porfirio Rubirosa had been one: five times married, former son in law of Rafael Trujillo, inverted the trope by becoming millionaire because of his talent with ladies, had a brilliant career as a diplomat, was a great racing driver and airplane pilot. (Unfortunately for him, he died appropriately, by crashing in a Ferrari.)
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.