Eccentric Millionaire

""I can do whatever I want. I'm eccentric. Rowr! Rowr!"

Donald Sinclair (John Cleese), Rat Race"

""Eccentric is Loopy with money."

Bob the Tomato, Veggie Tales"

The rich guy who believes in having fun with his cash, buying rich parties, helicopters, trips to the Titanic, whatever. This guy is definitely more fun than the standard tightwad image that accompanies most millionaires.

He also might just be an excuse for the main characters to be able to spend their time doing something besides earning money, since this guy is keeping them fed. When the writers of a comedy aren't in the mood to come up with a unique premise, he may also have set up a bet/challenge/goofy will/whatever for a huge amount of cash; Hilarity Ensues of course.

Compare with Uncle Pennybags, which is equally nice but not that of an overspender. Compare/contrast Upperclass Twit, Rich Bitch, Spoiled Brat, and Upper Class Wit. May be a Socialite, a Rich Idiot With No Day Job, as well as Rich in Dollars, Poor In Sense.

Anime and Manga

 * Honey, Sunako's aunt in The Wallflower who spends her time globe-trotting in a helicopter and schmoozing at parties. She also wants her dark niece to turn into a lady, and gives the job to four Bishonen in exchange for free rent in a mansion...if they succeed.
 * Lory Takarada, from Skip Beat, seems to believe that you couldn't enter in any building without a parade imported from the Rio de Janeiro's Carnival and dressing like the lovechild of Charirman Kaga and Walter Mercado. And pray he doesn't hear that you're planning a party, because he'll bring you the same design team who decorated Willy Wonka's factory. Well, he is the president of a big talent agency, so his eccentricities can be sightly handwaved, but still...
 * To a certain degree, Gary Oak from Pokémon. He is fairly rich, due to Professor Oak's research, and would easily qualify seeing as he not only spends all of his money buying cruise tickets, a week at the spa, a sports car most people would dream about and his faithful busty cheerleaders. He's ten, for Christ's sake.
 * Not to mention, spending your fortune on travelling across the world searching for pets (in a nutshell) is... Pretty wacko in itself.
 * Ouran High School Host Club....the Club itself, but hell, the entire freaking Ouran Academy. When Haruhi says "Rich Bastards" she isn't kidding!

Comic Books

 * Bruce Wayne, who, as a Rich Idiot With No Day Job, has a public image as above, but his real eccentricity is that he is the superhero, Batman (and borderline psychopath, depending on the writer).
 * Surprisingly, Marvel's Hercules. After his death, Namora and Venus go about trying to put all his affairs in order, and discover he owns everything from pleasure resorts to a hospital/orphanage for the children of mythological monsters. Also, a good chunk of his still-living ladies were gifted homes. Apparently, he made a few really smart investments, then just never bothered to keep up with them and bought whatever he damn pleased on the (correct) assumption that he just could.
 * Tony Stark, anyone?

Film

 * The deceased uncle in the various film (and theatrical) adaptations of Brewster's Millions (named Rupert in the Richard Pryor version, but given different names in other versions). Part of the bit is that he was the classic skinflint tycoon in life, but had enough guile to leave a booby trap in his will intended to make his inheritor hate spending money.
 * The Magic Christian revolves around Sir Guy Grand, a millionaire who uses his fortune to play cruel practical jokes on others.
 * Peter Sellers, who played Grand in the film (it was adapted from an earlier novel), was an excellent real-life example of this. In particular his passion for cars was so infamous it was referenced in The Goon Show and a sight gag in the short film Simon, Simon (his lovely sports car is run into; he steps out, snaps his fingers, and a new one in a different color is wheeled out for him to drive off in). His poor money management due to his tastes left him almost insolvent in the early 1970s. He was also a practical joker, but less cruel and destructive than Grand.
 * As the page quote indicates, John Cleese's character in Rat Race.
 * Felix Happer of Local Hero, a Big Oil executive whose office doubles as a planetarium and is willing at the end to spend untold millions  building an oil refinery.
 * Adam Sandler's uncle in Mr. Deeds fits the description before he dies.

Literature

 * Samuel Westing of The Westing Game fits this trope. He loved fire works, playing dress up, and generally messing with people. He also involves all the main characters in a complicated game for his inheritance.
 * Roarke, from In Death, is a multi-bazillionaire former thief with Only One Name who helps his wife solve murders as a hobby.
 * Elon Tessic of Shattered Sky is an eccentric multibillionaire who wants to spend his fortune in unusual ways. In one of his earliest scenes, we see him buy a restaurant-owner friend's pie recipe for millions of dollars.
 * Mr Toad in The Wind in The Willows could be a deconstruction on this trope; he enjoys blowing his inherited money on whatever he thinks is most enjoyable, from a caravan, to a motor car, but got in trouble when his obessive with motor cars went too far. And he risks losing his fortune on his obsessives when he could have used it responsibly to help him live his entire life comfortably.
 * Hubertus Bigend, the massively wealthy and Bunny Ears Lawyer-ish advertising exec whose plans and interests form the core of William Gibson's "Bigend Books".
 * In the highly metatextual Complete World Knowledge series, author John Hodgman claims to be the "Deranged Millionaire" he plays in some They Might Be Giants' work. See below under Music.

Live Action TV

 * Jimmy James from News Radio.
 * John Beresford Tipton, the mysterious Millionaire from the series of the same name. Even though he doesn't actually appear on screen, he acts as a trickster by throwing a disruptive catalyst (i.e., a check for a million dollars) into people's lives.
 * A Lampshade Hanging example from Mitchell and Webb.
 * Chairman Kaga in Iron Chef and his nephew Chairman Mark in Iron Chef America. The former is on record as stating he spent ¥843,354,407 just on ingredients for Kitchen Stadium (roughly $8 million at the time), while the latter has several Kitchen Stadiums built (including one In Space). And let's remember, this is to host Cooking Duels. If that ain't eccentric...
 * Thurston Howell III on Gilligans Island. He's so eccentric he uses his money as leverage on a deserted island.
 * In the 2007-09 series Life, Detective Charlie Crews definitely fits the bill. (If you were in the LAPD and they railroaded you for a murder you didn't commit, then you were exonerated years later and received a multi-million dollar settlement from the LAPD for your false imprisonment, would you really go back to work for the LAPD?)
 * In one episode, Crews encounters a support group for multi-multi-million dollar lottery winners.
 * One of the lottery winners in that episode had become so paranoid that he became a gun hoarder who built a high cinder block wall around his house.

Music

 * The Deranged Millionaire, a recurring character from the work of They Might Be Giants, played by author and comedian John Hodgman. He hosts the music video compilation/ConceptAlbum "Venue Songs" (and figures into the Myth Arc explaining the project), and has appeared in some of their stage performances and podcasts. See Literature, above.

Western Animation
"Minnesota Cuke: He's Loopy!
 * Señor Senior Senior and his son Señor Senior Junior on Kim Possible. The former decides to take up villainy as a post-retirement hobby and the latter is obsessed with hair gel and becoming a world famous pop sensation.
 * Franklin Sherman from The Critic
 * A one "Humphry Muffet" in a Veggie Tales short was one of these.

Bob: No, he's Eccentric.

Minnesota: What's the difference?

Bob He's rich. Eccentric is Loopy with money."


 * Super Chicken from George of the Jungle. His identity is millionaire playboy Henry Cabot Henhouse III (Hunt Strongbird Jr. in the unaired pilot).
 * An episode of American Dad has a popular hair dresser, named Beauregard, who moves to New York City from Langley Falls to carry on the city's tradition of "wealthy obnoxious weirdos".

Real Life

 * Canadian financier Charles Vance Millar was an infamous practical joker. His best known eccentricity was the Great Stork Derby, wherein Millar, having no heirs at the time of his death, left the majority of his estate to the Canadian woman who gave birth to the most children in the ten years following his death. Truth in Television, indeed.
 * The late Steve Fossett. He flew around the world in a balloon and a jet that didn't need refueling, both times solo, and set more world records than can be recorded here.
 * Howard Hughes was considered this back in the day, spruce goose Hercules being a major obsession, in hindsight though he had debilitating mental illness.
 * Billionaire clown(and CEO of Cirque du Soleil) Guy Laliberté plays high stakes poker for fun, and does quite well, possibly because the money involved is nowhere near enough to make a difference to him. In 2012 he announced a $1 million buy in tournament to raise money for a charity he founded. He's also been to space.