1. Sean Parker
Ways to measure your success as a playboy billionaire:
A) You’ve helped found several groundbreaking business ventures, including Napster, Facebook, and Spotify.
B) You’re a nonstop party-tron worth $2.1 billion at 32 years old, and regularly cited as the Andrew W.K. of the tech startup scene.
C) Justin Timberlake played you in a movie.
2. Richard Branson
What else is there to say about this jet-set billionaire Brit, Virgin Group mogul, and Conquerer Of Space And Time that hasn’t already been said? He’s like a dapper (and very English) Bruce Wayne, but without all of the horrible emotional trauma and bat fetishization.
3. Prince Azim
The playboy prince of Brunei is known just as much for his riotous partying as he is for the mile-long guest lists at each of his extravagant soirees. This is the guy that shelled out megabucks for Michael Jackson to play his 25th birthday party while we were slugging Schnapps in a McDonald’s PlayPlace ball pit. I guess doors really open for you when you look this much like Turtle from Entourage.
4. Paris Latsis
Poor, rich Paris Latsis. Despite being an heir to a multi-billion dollar shipping industry, this Greek socialite will always be known to the tabloid-reading public as “that guy that was engaged to Paris Hilton.” Or, perhaps more plainly as “the other other Paris. You know, the one that isn’t a city and didn’t make a sex-tape? Yeah, that one.”
5. Albert Von Thurn Und Taxis
How rich is German royal (and amateur Frodo impersonator) Albert Von Thurn Und Taxis? So rich that he bought a second mansion to house the rest of his last names! takes puff from comically oversized cigarette, novelty bow-tie spins But seriously, anyone who can afford to collect racecars as their personal hobby can, er, obviously afford pretty much anything.
6. Lapo Elkann
Formerly a staple of seedy tabloid exposés, this ultra-rich Italian industrialist has moved past, if not fully abandoned, his reckless playboy roots. Worth something to the tune of $7 billion, you’d think that this well-to-do womanizer could afford to fill up on gas. This economy, amirite?
7. Vikram Chatwal
Billionaire hotelier Chatwal might be better known to us blog-scouring commonfolk as the latest guy to get tangled up in the hornet’s nest of crazy that is Lindsey Lohan’s personal life. Or, oddly enough, as that guy in that scene in Zoolander, because what better measure is there for success than sharing a screen with Ben Stiller?
8. Gunter Sachs
Although he preferred “gentleman” over the more headline-friendly “playboy,” this classy Casanova did his fair share of wooing in his younger days. Like the time he flew over blonde bombshell Brigitte Bardot’s French home in a helicopter and dropped literally hundreds of roses on her lawn. This was admittedly some time before sexting became a thing, but it’s still pretty damn romantic in retrospect.
9. Stavros Niarchos III
Despite sharing his name with a chip dish at Chevys, this tabloid headline mainstay is known more for the rotating arm-candy he’s seen with than the billions in his bank account.
10. Matthew Mellon
Although this billionaire businessman is the heir to an impossibly wealthy banking family fortune, there’s a slight chance he’s not the sharpest tool in the shed. Or, in the words of his ex-wife during their very public divorce, “Matthew can’t even read a comic book, let alone a legal document.” Oof, I hope he used those billions to stock up on some burn cream.
Inspired by The CW’s “Arrow”
Devil-may-care billionaire playboy Oliver Queen’s core concerns were fast cars and faster living, but that was before the accident. Stranded alone on a deserted island, Queen recasts himself as a hardened survivor, willing to do whatever it takes to make it home alive. Long thought dead in the public eye, he returns to Starling City as the vigilante archer Arrow, hellbent on quashing the criminal element that’s run rampant in his leave.