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Millionaire Playboy

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Hugh Hefner knows how to accessorize.
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, swank tailored suits, lavish living in a downtown penthouse loft and a countryside mansion, 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 draws women to them in droves — and he exults in it, because he can have his pick among supermodels and starlets. Even if he's the type to love 'em and leave 'em, he knows there'll always be another to take their place, ensuring you'll never get as much action as he does. He is The Hedonist, so there may be a bevy of live-in girlfriends and mistresses.

The classic suit is the smoking jacket. Their 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 Product Placement. 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 La Bohème, and debate political issues.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 gourmands with a refined palate. Their wine cellar and liquor cabinet includes rare, imported bottles. Their drink of choice is an elegant cocktail. Pipes and fine cigars are also appreciated.note 

Favorite playboy hobbies include gambling at elite casinos (Blackjack, roulette, etc); hanging out with business elite at wood-paneled private club; gala, black tie Classical Music events; art openings at fancy galleries; auction houses for fine art; posh equestrian events and other Snooty Sports; 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 Caper Crew. Usually as the one covering the group's expenses, and just as likely to use their connections to bail the team out of a tight spot, should it become necessary.

Ones with fighting skills are likely to be Cultured Badasses. For villainous examples see Man of Wealth and Taste.

Spear counterpart to the Socialite.


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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 & Manga 
  • Roger Smith from the anime The Big O is a heroic millionaire who protects people with his giant robot.
  • 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.

    Comic Strips 

    Comic Books 
  • 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.
  • Green Arrow
    • 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 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.
  • Tony Stark, especially in the movies.

    Fan Works 
  • Billionaire Neptune in Roadside Assistance 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 so is his wife).

    Films — Live-Action 
  • Subverted in The Lover where The Girl's eponymous lover is a handsome and wealthy Asian hedonist, but is physically weak and lacking in self-confidence.
  • Tom Cruise's character in Vanilla Sky.
  • 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 cameo.
  • Bruce Wayne in Batman Begins pretends to be one as part of his Idle Rich guise, but only as a distraction to provide cover for his Batman Secret Identity. It wasn't played up in subsequent films, as the point had cinematically been made.
  • Derek Flint in Our Man Flint 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, In Like Flint, he was 'trying to cut down' and had only three (live in, anyway).

  • Tsu Ma in David Wingrove's Chung Kuo series. It helps being the supreme lord of West Asia.
  • 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 
  • Kang Hyun-min from Cinderella and the Four Knights 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 Desperate Housewives.
  • Chuck Bass from Gossip Girl.
  • Smallville's Lex Luthor, although the playboy part is more reputation.
  • Amos Burke on Burke's Law.
  • Arrow. Oliver Queen along with his Romantic Wingman 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 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 
  • 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.

    Visual Novels 

    Western Animation 
  • Xander Crews from the show Frisky Dingo 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.

    Real Life 
  • Hugh Hefner was one, as reflected in the name of the magazine he founded. As such, he is the trope namer, in addition to being an iconic example of the luxurious, hedonistic lifestyle.
  • 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.)
  • 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 an entirely new trope.