Millionaire Playboy

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.

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 fits this trope very well.

Comic Books

 * Bruce Wayne acts like this in some continuities.
 * 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.

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 while the playboy part is more reputation.

Real Life

 * Hugh Hefner is one, as reflected in the name of the magazine he founded.

Video Games

 * Tales of Symphonia's Zelos Wilder

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.