Uncle Pennybags



This is a person, usually male (if not, meet Aunt Pennybags), who, despite being ludicrously wealthy, is actually a fun guy to be around, even if you're dirt-poor. He's often an Affably Evil Corrupt Corporate Executive or an Honest Corporate Executive. He will often be a Good Samaritan, using his massive hoard of money to help people. Often a Self-Made Man; if not, likely to be a grown up Spoiled Sweet.

Not to be confused with Rich Idiot With No Day Job, which is when this is used as a cover for a Secret Identity.

This trope name comes from the mascot of the board game "Monopoly" (first name Milburn), who was renamed "Mr. Monopoly" because people just called him that anyway.

A Sub-Trope of Idle Rich.

Anime and Manga

 * Eduard aka Estonia from Axis Powers Hetalia is a BROTHER Pennybags.
 * Ayaka Yukihiro of Mahou Sensei Negima, willing to fund trips to the south seas, fly a dozen people to the UK, and entire festival games well into the millions, usually without being asked. At points, she will add in "My peasant friends" and the like to hold her Rich Bitch status. Her character assures that The Author has no unavailable plots.
 * Pretty much the entire cast of Ouran High School Host Club, aside from middle-class scholarship student Haruhi, but especially Tamaki.
 * Pokémon Special has Misty and Gold qualify for this role, even if Gold happens to be a jerk at times. Steven, for being the Champion of Hoenn, is one of these due to being Devon Chairman Stone's son. While she has the money, Platinum doesn't qualify... yet.
 * Souichirou Mikuni. Granted, he may not be all nice, and he's not cheery and sociable per se, but he's still much nicer than everyone else with his kind of money.

Comic Books

 * Richie Rich.
 * Tony Stark, alias Iron Man, from the Marvel Universe.
 * The Green Team: Boy Millionaires from The DCU.
 * Thomas and Martha Wayne from Batman are both philanthropists as well as their son, Bruce, who runs his Wayne Foundation as a way of preventing and mitigating crime in ways Batman can't. One Jonah Hex storyline shows that the Waynes' ancestors were also good people who were not corrupted by their wealth and power.
 * Scrooge McDuck didn't start out this way, but evolved into one in most interpretations. He's still ridiculously greedy, of course.
 * He's not very friendly or sociable, but if you get into his good graces, he'll take you along for countless incredible adventures - you won't see any of the possible profits, though, and expect below minimum pay, if even that.
 * Veronica Lodge's father Mr. Lodge is an overall nice guy and could be considered one of these, at least when accident-prone Archie isn't giving him ulcers by destroying some priceless treasure.
 * In the Alternate Continuity timelines of Life With Archie: The Married Life, he has pretty much crossed over into Corrupt Corporate Executive territory, sabotaging Archie's marriage to Veronica in one universe and destroying Archie's musical career in revenge for breaking Veronica's heart in the other.
 * Iron Fist.

Fan Fic

 * Naruto, of all people, become on in Kitsune On Campus when he . Needless to say, he does not comprehend. His money is used to fund part of the Mahora Festival, which he has absolutely no problem with.

Film

 * The hero's best friend becomes one of these in the movie Envy. He continues to treat the main character well, even as the main character's envy causes him to hate and ignore his friend.
 * The main characters' ludicrously wealthy friend in Benchwarmers, who is implied to keep $1 billion on his person, and uses his colossal money to build his friends a baseball stadium
 * The old guy whom Morgan Freeman's character befriends in Bucket List.
 * Thornton Melon from Back to School.
 * Mr Bigweld from the film Robots was, at least at some point, something like this.
 * Johnny's girlfriend's uncle Mike is one of these in Poolhall Junkies. After being impressed with his pool skills earlier in the movie, he shows up to back Johnny up with a Briefcase Full of Money during the showdown at the end with Johnny's old hustling partner. The hustling partner promptly dubs him "Daddy Warbucks".
 * In Garden State, one of the main character's old friends made millions by inventing noiseless velcro, and seems to do nothing but throw parties for his friends.
 * "Big Daddy" LeBouf of The Princess and the Frog is the richest man in New Orleans, but is quite friendly and treats his employees with genuine respect. Most of his money seems to go to doting on his Spoiled Sweet daughter - who, being Spoiled Sweet, tends to be another economic force for good.
 * Meet Joe Black: Anthony Hopkins's media tycoon.
 * Pretty Woman: Ralph Bellamy's shipbuilder tycoon whose company is the target of Richard Gere's character's corporate raid. At the end of the film, Richard Gere's character as well.
 * Fitzwilly's Miss Woodworth is all too willing to give money to any worthy cause, a matter complicated by the small fact that she doesn't actually have a fortune, necessitating her servants pull off one con after another.
 * Rodney Dangerfield played roles like this in films such as Caddyshack or Back To School. While not as ultra-rich as most examples, his characters tended to give away gifts or money like there was no tomorrow, and were rude, yet fun to be around.
 * Mr. Duncan from Home Alone 2. An owner of a toy emporium, a philanthropist and generally a great guy.

Literature

 * One of Kinky Friedman's friends in his novels is a "decamillionaire" who's happy to help him if he needs a flight to Hawaii or something.
 * Just about every single PG Wodehouse protagonist, and all of their friends.
 * Watson Brewer, Kristy's millionaire stepfather, in The Babysitters Club. Doesn't mind inviting six or seven extra teenage girls to most family vacations.
 * Lord Peter Wimsey acts as an Uncle Pennybags to almost any character who is not wealthy or an antagonist. He's an excellent tipper, for instance, and being a bit character who helps him with an investigation is almost always profitable.
 * Charles Dickens was fond of this trope. See the Cheeryble brothers in Nicholas Nickleby, John Jarndyce in Bleak House, and of course Ebenezer Scrooge after his reformation.
 * Cordelia Naismith in the Vorkosigan Saga. Although its established that The Vorkosigan clan wasn't exactly stingy with its subjects before she married Aral, Cordelia established a hospital (because she noticed that only military got the best medical assistance in Barrayar) and several scholarship projects (including one that sends lucky Barrayaran girls to ultra-liberal Beta Colony), among other projects. Miles also became a serious supporter of public works and education in his district, following his experience among his rural subjects in The Mountains of Mourning.
 * This is a very clever move if you realize that Barrayarans can only vote with their feet. Her actions resulted in her district getting a young highly educated population, it will make the Vorkosigans long term winners in the demographics game.
 * This happens all the time in 'The Paid Companion' by Amanda Quick.
 * Harry Potter himself has shown an inclination to be this, especially to Ron—to the latter's chagrin.
 * In M.Y.T.H. Inc. Link, Tananda is sent to collect on a debt owed by a fellow who turns out to be one of these.
 * On the Discworld, specifically in Raising Steam, Sir Harry King is revealed to be this. He worked his way up from the gutter and hasn't forgotten what it was like. He'd punch you in the mouth (and he's still got a hard punch) if you called him a philanthropist, but his employees get pensions when they retire, and their significant medical expenses tend to be taken care of once Sir Harry learns about them.
 * When two fellows who weren't his employees — they were in fact trying to become his competitors — accidentally blew themselves up, Harry thought about their widowed and now childless old mother ... and arranged a pension for her.

Live Action TV
"Gomez: How much for the suit? Street Corner Santa: Twenty? Gomez: Allright ... twenty thousand dollars. Santa: Mister, you don't need the suit!"
 * The dad on Silver Spoons.
 * Pete Becker from Friends. This is justified by him being a Bill Gates spoof who invented the premiere operating system in the world in his garage at a ridiculously young age.
 * Charlie Crews in Life has millions due to a lawsuit against the police department. He's a pretty fun guy to be around, too.
 * Jimmy James in News Radio.
 * Rocky, Lionel's dad, on As Time Goes By.
 * Alastair is a younger version of this, though he often comes across as an Upper Class Twit at times.
 * Gomez Addams would be practically the embodiment of this trope if not for the fact that, as an Addams his idea of "fun" tends to be "somewhat different" from what normal people might consider fun. Still, he's unfailingly kind to everyone he meets and throws away craptons of money on everything from supporting a local politician to saving a local swamp from being drained.


 * The Secret Millionaire is a reality show based on this concept. A rich person goes undercover in an underprivileged area of the UK, meets the locals and, in The Reveal, then hands out massive cheques to help them with projects to improve the area.
 * Besides the "money bringing him disgraces" part, Hurley from Lost.
 * Despite the name, Rick Castle (say it fast), is one of these. If a problem can be solved by throwing money at it, he never hesitates to reach for his wallet, and he throws great parties for his friends.
 * Which becomes plot-relevant every now and then when he contributes large sums of cash to police investigations that couldn't move forward without a budget, such as.
 * Bill and Judy's neighbor in Still Standing
 * Shrug (that was his name, don't ask) on the short-lived sitcom It's Like, You Know..., was a "retired internet billionaire" who had gone into acting. Despite being rich, he lived like most struggling actors lived (minus the poverty), threw great parties, and never hesitated to give out money to whomever needed it.
 * Stewart Babcock, C.C.'s father in The Nanny episode "Ode to Barbara Joan", despite C.C.'s warnings of him being the complete opposite. It turns out that he's just not that way towards her. Ultimately, the conflict brought out of this leads to a father-daughter reconciliation thanks to a little help from Fran.
 * In the short lived TV series Three Moons Over Milford, one episode focused on a happy wealthy old man willing to pass around outlandish amounts of money to random people in exchange for them doing childish dares, such as asking a waiter to do a headstand in the middle of work. He does this solely because the world could end any minute and he wants to give people gifts while getting a few people to smile at the same time.
 * Faith in Buffy the Vampire Slayer, believe it or not. Throughout the series she is more the Perpetual Poverty type, however in the comics she works with Giles. After  she discovers that she had been left a fortune. As well as being really fun to be around, Faith uses the money to help, such as using it to bail out a Slayer from a beating.
 * In Smallville, Clark and his friends benefited vastly from a series of sugar daddies. First, from Seasons 1-4, Lex Luthor often bailed Clark & friends out of their money troubles, as he was still essentially trying to buy Clark's friendship. After Lex gets caught using armed and superpowered thugs to hold Clark's parents hostage (and thus force him to reveal his secret if it had gone as he'd planned) in Season 5, Clark distances himself from Lex. However, Lex's Archnemesis Dad Lionel steps in and starts eagerly playing the role of Uncle Pennybags in a desperate attempt to impress Martha with his generosity. Lex occasionally still chips in money, but only in odd circumstances when he and Clark are thrown into a position where their interests coincide. Then from Season 6 onwards till the end, Oliver Queen steps in as Team Clark's big financier, as he is the major backer of the Justice League, eventually being joined in this role by former Dark Action Girl Tess Mercer in the later seasons.

Music

 * The "true love" in "The Twelve Days of Christmas", FULL STOP. Some folks have actually done the math and discovered how much all those gifts would cost. It's A LOT, considering they're gifts.

Newspaper Comics

 * Oliver "Daddy" Warbucks in Little Orphan Annie.

Professional Wrestling

 * WWE wrestler Triple H was implied to be an Uncle Pennybags to his friends in one storyline. As the story goes, Shawn Michaels lost his life savings in the stock market crash of October 2008, and so was forced to work for JBL as a "bodyguard" and interfere in matches on his behalf. Triple H approached Shawn and asked him why he didn't just come to him for the money; he certainly had enough, and he'd be willing to give Shawn as much as he needed, no strings attached. Shawn replied that he didn't want to take money from HHH, for fear of it ruining their friendship.
 * This could have been a rare shout out to Triple H's original gimmick in the WWF - Hunter Hearst Helmsley, ultra-wealthy American blue-blood. Although at the time Helmsley was much more of a Mr. Burns than an Uncle Pennybags.
 * Or, it could be because he IS filthy rich now, being married to the boss's daughter and all.
 * Ted DiBiase Jr's current gimmick in WWE is Uncle Pennybags. He's been given a massive trust fund from his father, "The Million Dollar Man" Ted DiBiase, and he mostly uses it to give gifts to the fans, have massive tailgate parties in the parking lot of WWE events with his Twitter followers, and donate to charity.

Video Games

 * Ken Masters, notably in the Street Fighter II: V anime series. During the first half of the series while he and Ryu are Walking the Earth, he uses his family's mammoth fortune to help those around him; from the relatively minor instances of setting he and Ryu up in a 5-star penthouse suite and buying Chun Li clothes and jewelry as a gift for her serving as their tour guide, to singlehandedly arranging for a massive donation and Red Cross assistance to a remote Indian charity hospital.
 * David Sarif from Deus Ex Human Revolution is ultimately one of these, despite committing a handful of shady actions (which mostly tend to come across as a necessary evil to survive in the cutthroat Cyberpunk business world).
 * Rodrigo Briscoletti from Dragon Quest V is this trope in spades. He's world famous for his wealth and generosity, and he gets a lot of that wealth from running a casino resort. You can choose in the game to marry one of his two daughters, and he'll lavish gifts on you on your journey. But even if you marry your childhood sweetheart instead, he'll still give you a family heirloom (a legendary artifact you're searching for), pay for your wedding to Bianca, let you stay for free at his casino, and give you one of his ships to set off in just because he likes you. What a guy!

Webcomics

 * Ray Smuckles in Achewood.
 * Llewellyn from Ozy and Millie fits in here, too. He cites gold as stuff he and his family throw at people when they want them to go away, and in one collection, tries to make gold into cookies. (It works, sort'a.)
 * Stasia from Marry Me, who is a wealthy celebrity sensation, who also donates a large amount of all her money regularly to various charitable organizations, and visits needy places in Africa on a whim.
 * The Inexplicable Adventures of Bob—Rocko recently became rich. So far at least, it doesn't seem to have gone to his head. When Bob had to leave on a long trip, Rocko agreed to man Bob's newsstand for him, since he was bored having nothing to do since he got the money. He's also paid to fix Bob's incessant roof damage twice.

Web Original

 * Whateleyverse's Ayla fits in here (when his friends don't forbid him from spending money on them, anyway). Depending on the story, it varies from being implied to outright stated that he was raised both to view money as just a tool to do things with, and with a strong sense of noblesse oblige; the combination means that he doesn't see the point in not using his money for good works. It's generally implied that his family is in the habit of doing the same thing; it gets mentioned off-hand in one story that there are a lot of buildings and public works out there named after various members of the Goodkind family.
 * He's rich enough to take certain luxuries for granted, and kind enough to feel bad that other people don't have them. And he's smart enough to actually invest her money in other things, and half of his good deeds make his money in the long run.
 * The Goodkind family as a whole play with this trope: while they see causes that they contribute as being necessary for the good of everyone, and honestly are trying to improve the welfare of humanity as a whole, the fact remains that they are also seen by most of the protagonists as a corrupt family who want to see the genocide of mutantkind. That view isn't necessarily wrong.

Western Animation

 * Fancypants from My Little Pony Friendship Is Magic, an upper-class Canterlot unicorn with a huge amount of pull in with the Canterlot elite. He's also a true gentleman who treats Rarity with the utmost respect
 * Diamond Tiara's dad, Mr. Filthy Rich. He wears his status on his sleeve, but he's pretty respectful towards Granny Smith.
 * Arthur Fortunes was a one-episode character on The Simpsons (specifically, the episode "Monty Can't Buy Me Love"). He's exactly like this.
 * Which may have been an allusion to Arthur Bach, the titular character of the 1981 movie Arthur, who was also like this.
 * Mr. Dink in Doug.
 * Jerrica 'Jem' Benton from Jem and The Holograms fits here as well....and Howard Sands to a lesser degree.
 * Most of the cast of Beverly Hills Teens, aside from the two Rich Bitch characters.
 * Goldie Gold, from Goldie Gold and Action Jack
 * Scrooge McDuck is like this in some interpretations, most particularly the 1980s cartoon DuckTales.
 * The cats from Catscratch.
 * Sunny and Eddie from Class of 3000.
 * Hiroshi Sato from The Legend of Korra is a Rags to Riches Self-Made Man who gave Republic City the Satomobile, the affordable common man's motor car. He runs a huge factory, and shows up at the most important social occasions. But he is a very easygoing man who is sympathetic to Mako, whom he sees as someone like his younger self; motivation but no means. Hiroshi honors his own Uncle Pennybags benefactor from his younger days by acting in the same manner to Mako by sponsoring his pro bending team.

Real Life

 * Millionaire philanthropist Andrew Carnegie held himself up as an exemplar of this trope (though the reality of the matter differs depending on who you ask). He certainly did give away mountains of moolah to charity and public works, in any case.
 * Similarly, whatever else you say about Andrew Mellon, you have to admit that he dumped his entire—phenomenal—art collection on the Smithsonian Institution, funded (through a trust) the construction of a place to store it, and placed as condition only that it not be named for him.
 * As the linked website should suggest (all Smithsonian sites are si.edu), the National Gallery of Art is NOT part of the Smithsonian. (Just try and use a member or employee discount in their gift shop.) That's right, Mellon gave them so much money and art they created a whole new museum organization instead of just sticking it in the one they already had. (James Smithson himself probably qualifies as well—he left his entire fortune to the United States government to create an institution for the dissemination of knowledge, despite never having set foot in the U.S. in his lifetime.)
 * Similarly, other huge-scale philanthropists like Alfred Nobel (who combines this with The Atoner, as he had gotten rich as an arms merchant) or Bill Gates.
 * Nobel's an interesting case, because his invention of dynamite was itself a philanthropic effort that saved many lives by putting the explosive nitroglycerine into a form that could be handled safely. It's said he became The Atoner after journalists began painting him as a merchant of death after others started using it for more nefarious martial purposes.
 * Billionaire Warren Buffett plans to be the most generous philanthropist in history, with over 83% of his fortune earmarked for charity. He has already made the single largest charitable donation in history, at over $30 billion. He also lives in a house he bought for $30,000 (in the 1950's, but still ) and takes pride in living only on his $100k salary.
 * Richard Branson seems to be the modern-day embodiment of this trope. He's ridiculously wealthy and spends his free time going on adventures, trying to float around the world in a balloon, and building a spaceship (which he dubbed "Enterprise", of course).
 * Of course NASA is backing him up with the spaceship since there's going to have a five year gap of not having a ship once they retired the Space Shuttle.
 * Being around Bill Gates and Richard Branson seems to have rubbed off on Yoshiki Hayashi, who just began an official charity. Though there may be another motive for this....
 * J. K. Rowling has donated a buttload to charities. Case in point.
 * She's also an outspoken democratic socialist, having lived in poverty.
 * The entire Rockefeller family. Adjusting for inflation, John D. Rockefeller died worth $318 billion. He gave away (again, adjusting for inflation) $9.5 billion. His descendants have given away even more.
 * John Rockefeller was a great guy to work for too, paying no attention to a new accountant who was fantastically rude to him when before he knew he was speaking to Rockefeller.
 * $9.5 billion is a lot of money, but it's underwhelming when one looks at it as less than 3% of the total worth.
 * Still pretty nice though and definitely counts as this trope.
 * Many lottery winners become this. It rarely lasts long.
 * Largely because most lottery jackpots, while huge from the perspective of an ordinary person, don't settle you for life unless you invest it responsibly, something that most lottery winners have hard time understanding. That, and if you become known as the guy who practically throws money away, you quickly are swamped by plenty of people with dubious intentions.
 * Actually, it's not just lottery winners. A study was performed and they found that this happened when anyone got a big (relatively speaking) sum of money. For instance, they gave a homeless man $40,000 dollars. Within a month, he was homeless again and had spent/given away/otherwise used up all that money. People generally do better handling small windfalls, such as a few hundred bucks, than large ones, such as thousands, due to having more experience with the smaller amounts.
 * After his famous climb, Sir Edmund Hillery in gratitude to the Sherpa people devoted his life to helping them. Several Sherpa students at schools he founded know him better as the founder of their school than as a climber.
 * Walt Disney.
 * Santa Claus, who is often described as a reverse Robber baron.
 * Hoqua, perhaps the most famous hong (guild) master in Canton had that reputation amid hard nosed Ammerican and British clipper barons. Several dynasties have a portrait of him in their collection and one clipper was named after him.
 * It was one of the traditions of the early middle ages that a Teutonic noble should be this and give out dramatic gifts. In a sense that was his warband's pay. This tradition continued, indeed is well-known in a lot of times and places. But it was an especially important part of the code of honor of the time. For instance a poetic word for King was "ring-giver".