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- 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.
- In Tokyo Ghoul, Tsukiyama's grandfather was apparently an infamous womanizer. His father worried he would turn out the same as a result of his School Idol status, but this turns out to be an unfounded concern.
- 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.
- 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".
- Bruce Wayne was one in Batman Begins, as part of his Rich Idiot with No Day Job guise, but grew out of it in subsequent films.
- 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.
- 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 Burke's 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.
- 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.
- Lorne de Havilland, one of Agent 47's targets in Hitman: Blood Money. 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.
- 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 by crashing in a Ferrari.)