I have men on command
I have always a shilling to spare
So be easy and free
When you're drinking with me
I'm a man you don't meet every day.
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 Honest Corporate Executive, though occasionally he might be an Affably Evil Corrupt Corporate Executive, or else probably one of the Idle Rich. He will often use his massive hoard of money to help people. Sometimes a Self-Made Man; although in older works, he's more likely to be an Upper-Class Twit who averts Aristocrats Are Evil.
Often The Team Benefactor.
This trope name comes from "Rich Uncle Pennybags", the mascot of the board game Monopoly (first name Milburn), who was renamed "Mr. Monopoly" because people just called him that anyway.
Compare/contrast with a Wealthy Philanthropist who focuses more on actually helping people with their money than having fun and Beleaguered Benefactor.
- In Beauty and the Feast, Yamato's mom Kyouka has no problems showing Yakumo her gratitude for taking care of her son, giving Yakumo an entire bag full of expensive designer perfumes as a thank you gift. She reasons that with how much her son eats, this is the least she could do to make up for the expenses.
- Souichirou Mikuni from [C] – Control. 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.
- Dragon Ball:
- Bulma has shades of this, being the heiress to the Capsule Corporation. She spares no expense at her birthday party in Dragon Ball Z: Battle of Gods, providing the best food and entertainment available and offering lavish games prizes such as a full-sized castle and the seven Dragon Balls. In Dragon Ball Super, she regularly feeds Beerus and Whis at the finest restaurants at great expense (though this is largely to keep them from destroying the earth), allows the Pilaf Gang to mooch off her hospitality for unclear reasons, and when the cast are arguing over who gets a wish from Shenron the wish-granting dragon, she gets most of them to rescind their claims by just buying what they want.
- In Super, Mr. Satan has taken up this role, using his wealth to buy nice things for his son-in-law and giving Goku the one-hundred-million zeni he'd won for the World Peace Prize, both to subsidize Goku's lifestyle, and to reward him for saving the world many times in the past.
- Eduard/Estonia from Hetalia: Axis Powers is a Brother Pennybags. He has much more money and resources than his "brothers" Lithuania and Latvia due to tourism and is willing to help them out if they need bucks.
- Sheryl Nome from Macross Frontier. She's kind of a Tsundere Alpha Bitch Idol Singer, but if someone she has a soft-spot for needs help and she can pay for it, she'll do it without hesitation. For example, she has a credit rating high enough to hire an entire high tech mercenary unit complete with their carrier flagship and Super Prototype fighters for a high-risk rescue mission... with just her credit card.
- Ayaka Yukihiro of Negima! Magister Negi Magi, 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.
- Her great-granddaughter Mizore fills the same roll in UQ Holder!.
- One Piece: Kaya is a kind young rich girl who is sweet, likes listening to Usopp's stories (which are lies), and has her butler Merry build the Straw Hats their first pirate ship, the Going Merry, as thanks for them saving her life and her village.
- Pretty much the entire cast of Ouran High School Host Club, aside from middle-class scholarship student Haruhi, but especially Tamaki.
- Pokémon Adventures 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.
- In Rebuild World, Akira foots the bill for Sheryl's gang on multiple occasions, such as paying for new clothes for Sheryl to help her with relic negotiations and laying down some cash for Sheryl to feed the younger orphans good food and teach them to read and write. While this is largely selfishly motivated due to his belief that these actions will either make him money or give him better luck, it also shows that he's not as stingy or unreasonable as he appears.
- Not that Shirobako's Aoi's older sister Kaori is rich, much less an Idle Rich, but even at her provincial bank she's paid several times more than Aoi and her friends (especially Ema), so she keeps her wallet wide open when she visits her sister on a vacation.
- Mimori Unyuu from Sket Dance is the heiress to the Fiction 500 Unyuu group who tends to use her wealth to help out her friends. Of course, being Rich in Dollars, Poor in Sense, her "help" often comes across as a nuisance instead.
- Hyoutei's captain Keigo Atobe in The Prince of Tennis. When he entered Hyoutei as a first year, his family upgraded all of the tennis facilities and even the cafeteria with five-star meals, and when Ryoma goes missing before the National tournament finals, Atobe takes Momo in his personal helicopter to find him. One of the data points in the fanbooks is what each character spends their allowance on, and Atobe spends his on spoiling and treating his club members.
- Charles Xavier used his considerable family fortune to open the Xavier School, a safe haven for mutants with nowhere else to go.
- Richie Rich. He's the world's richest child, yet has the moniker "poor little rich boy" precisely because he's kind and charitable towards others.
- Tony Stark, alias Iron Man, from the Marvel Universe.
- Janet Van Dyne, alias The Wasp, also from Marvel, started out as a Rich Bitch but evolved into this.
- The Green Team: Boy Millionaires from The DCU.
- Rebooted as Teen Trillionaires. They're constantly looking for fun ways to spend money — the first issue of the new series goes into detail about Commodore's "Pop Up Expos", where he takes his pick of emerging technologies to fund.
- Thomas and Martha Wayne from Batman were both philanthropists, as is 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.
- Disney Ducks Comic Universe:
- Scrooge McDuck didn't start out this way — as seen in The Life and Times of Scrooge McDuck— 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.
- Subverted in one of Italian comics, where his "projects to society" are actually a way to benefit himself. Double Subverted when it's revealed that the philanthropist guy got his funds from him.
- A recurring plot point in Italian comics is Donald Duck and others trying to get Scrooge to give money to various charities or otherwise being generous by winning a bet with him — with Scrooge helping them in secret because he doesn't want to appear generous or (worse) soft, and the rare times he's found out the others agree to keep the secret. An insert in the Italian Mickey Mouse magazine also reveals he regularly makes generous donations to charities, he just hides all evidence.
- Scrooge is sometimes written as a literal An Economy Is You, who has to spend money lavishly in order to keep himself in business — any given corporation being owned by him, he can't do anything that would save him money without costing himself an equal amount, so he might as well be generous.
- Scrooge will give out money to a worthy cause or an honest entrepreneur. The trick, however, is convincing him you are worthy, as he's heard so many handout requests that he dismisses most pleas for money out of habit. But he has invested in numerous business startups by honest people who are willing to work hard. In one story book, when Huey, Dewey, and Louie are holding a bake sale to save Grandma Duck's farm, Scrooge applauds their efforts and promises to match their dollar take two-to-one.
- One special Christmas comic shows Donald and the nephews lamenting Scrooge's alleged heartlessness, juxtaposed with a series of letters he receives over several years. A young girl orphaned by her mother's death has her entire education financed secretly by Scrooge, and she writes him regularly to show her appreciation. The salutation on the letters shows how he evolves from being "Mr. McDuck" to "Uncle Scrooge" in the young woman's eyes.
- Archie Comics: Veronica Lodge's father, Mr. Hiram Lodge, is really an overall nice guy and could be considered one of these, at least when accident-prone Archie or Jughead aren't giving him ulcers by destroying some priceless treasure or forcing him to pay millions to repair the damage caused by their adventures. However, 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.
- The Invisibles: Mason Lang is a good example of this. He is an incredibly rich Honest Corporate Executive, he fully supports La Résistance with all his wealth and influence (without really being a full active member), and he is overall a fine and friendly guy.
- In Circles, Paulie is a very friendly and rich man and a lot of fun to hang around with.
- R.J. Brand, the guy who decided to form the Legion of Super-Heroes in two of their three incarnations, is the third-richest being in the entire Milky Way, making his fortune off building suns/developing stargate technology (it depends on the continuity). After being rescued by Rokk Krinn, Imra Ardeen and Garth Ranzz, he decides to form them into the Legion of Super-Heroes, builds them a clubhouse/headquarters, and funds everything they do. He's known for being incredibly personable and has a heart of gold.
- In 1955, Charlton Comics introduced Uncle Giveaway, a portly, mustachoid older fellow not too dissimilar in appearance from the Trope Namer. Jack Kirby was at least partially credited for his creation. Uncle Giveaway wished to be a heroic crime fighter, but the only power he truly had was being obscenely rich ("moderately less than Santa Claus"). So instead, he resolved to do good by generously giving out prizes. This was the setup of Win a Prize Comics, a series in which Uncle Giveaway would host a number of different stories, and even star in a few adventures himself. At the end of each story, Uncle Giveaway would pose questions, and 500 of the readers that successfully answered would win a real life prize! Unfortunately for the old Uncle, Win a Prize Comics only lasted two issues. On the flipside, he's apparently now in the Public Domain, so feel free to create your own stories starring the selfless billionaire.
- Oliver "Daddy" Warbucks in Little Orphan Annie.
- In one chapter of Sister Floriana, Sister Isabel has an uncle who buys her and her friends a dozen pairs of roller skates at the drop of a hat.
- Naruto, of all people, become on in Kitsune On Campus when he reintroduces the Icha Icha series to the world by publishing it in Mahora. 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.
- This has become quite common in Naruto crossovers as a way of hand waving whatever monetary problems Naruto could have after becoming either a Dimensional Traveler or The Ageless (the most common causes of the crossover itself).
- Downplayed in Loud 10 where Lincoln sells some of the crystals Diamondhead makes to buy Leni a car.
- Varric is this at Skyhold Academy. He has plenty of Impossibly Cool Wealth, and his favorite thing to do with it (apart from spoiling his friends and Love Interest) is to buy ice cream and other treats for the students at the school where he teaches. Most of his gifts are made anonymously, because — in the words of one of his colleagues — he likes to feel sneaky.
- Roxas proves himself to be very generous with his munny in the Kingdom Hearts/Game of Thrones fanfic A Song of Fire, Ice, and Hearts when he pays off the 3 million gold debt the Iron Throne owes the Iron Bank of Braavos, with plans to also pay the equally expensive debt owed to the Lannisters.
- White Sheep (RWBY): Roman Torchwick invokes this with Jaune's sister Lavender, figuring being the "cool uncle" and buying her stuff like an apartment is a safe way to make himself indispensable. She actually has far more money than him and could easily make do without him, but she allows the charade to continue because it's convenient.
- Mr. Bigweld from the film Robots was, at least at some point, something like this.
- "Big Daddy" LeBouf of The Princess and the Frog is the richest man in New Orleans, but is quite friendly and treats his employees and other individuals (no matter their class or race) with genuine respect. Most of his money seems to go toward doting on his Spoiled Sweet daughter, who tends to be another economic force for good.
- Eddie from Sing qualifies; he comes from a very wealthy family, and is friends with Buster Moon, owner of the dilapidated Moon Theater. Early in the film, it's established that the only reason Buster's theater hasn't gone under yet is that Eddie invested heavily in Moon's productions, but after a series of flops, his family refused to allow Eddie to give Moon any more money. When Moon is reduced to washing cars after the theater collapses, Eddie gladly helps him and even acts as the light and sound technician when the talent show is performed in the ruins of the theater.
- Winston Deavor in Incredibles 2. He is a rather eccentric but kind, successful tycoon who heads a billion-dollar telecommunications company he inherited from his late father. He also inherited from his father a love of superheroes and believed superheroes being made illegal to have been the cause of his father's death. He wants to use his money and connections to organize a PR stunt to make superheroes legal again with Elastigirl as the head super in this (the logic being she caused the least amount of collateral damage). He pays her well for this and even gives her family a house to live in after they had been living in a motel following the events of the first film. When his sister tries to foil his plan to relegitimize superheroes, he refuses to escape with her and returns to the Everjust to destroy the screens hypnotizing the ambassadors and get everyone to safety.
- The Cannonball Run: In contrast to his Jerkass behavior in the first film, the Sheikh is quite generous with his money beyond the point of just showing off. He gives complete strangers enough money to buy a clothing store just because he thinks their clothes are shabby, offers a large prize for the winner, doubles it without needing to, and gives a business partner who is millions in debt twice what the man owes a Loan Shark so his new friend can have extra "petty cash".
- 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 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 The Bucket List.
- 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.
- Meet Joe Black: Anthony Hopkins' media tycoon.
- Pretty Woman: Ralph Bellamy's shipbuilder tycoon owns a company which is the target of Richard Gere's character's corporate raid; as we find out in the course of the story, though, he's an incredibly Nice Guy. By the end of the film, Richard Gere's character has become this as well.
- Fitzwilly: 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, requiring her servants to pull off one con after another.
- Rodney Dangerfield played roles like this in films such as Caddyshack and 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: Lost in New York is the owner of a toy emporium, a philanthropist, and generally a great guy. He apparently makes a habit of personally working the register at his stores so he can watch the children enjoying their new toys.
- Arthur Manleder from the Boston Blackie movies.
- Daniel Clamp, of Gremlins 2: The New Batch, was originally going to be a thoroughly-unlikable character (and, as the name implies, a parody of Donald Trump). The actor, John Glover, apparently sick of being Typecast as the Corrupt Corporate Executive, talked the director into letting him play the character as this trope.
- X-Men Film Series:
- X-Men: Professor X mentions that most of his students were runaways, so his school isn't just a centre for education, but also a safe haven for a lot of the youngsters who don't have a home.
- X-Men: First Class: Xavier's generous nature is alluded to in this exchange:
Sean Cassidy: (in awe of Xavier's mansion) This is yours.
Charles: (smiles) No, it's ours.
- The Wolverine: Ichirō Yashida was apparently a very benign and kind CEO, always helping the poor.
- X-Men: Apocalypse: Before the events of this movie, Charles wasn't interested in reinstating the X-Men, yet he still allocated a ton of cash to Hank so that the latter can create a new model of the Blackbird. There's no logical reason for Xavier to do this other than it being a very expensive way for him to assuage McCoy's worries that humanity might turn against mutantkind in the near future. Charles' attitude seems to be something along the lines of, "Hank, I think your fears are unfounded, but I'll let you build a warplane if it makes you feel better." Professor X is an extremely indulgent friend!
- The title character in both versions of Arthur (1981) comes from a ridiculously wealthy family and has never had to hold down a job, and thus spends his days being Fun Personified, cracking jokes to any prospective audience he encounters. His stuffy family and their social circle don't approve of his playboy antics and find him annoying and embarrassing, but people outside of it — including the working-class woman he falls in love with — are more forgiving. Ironically, this romance puts him on the path to actually maturing at long last, rather than the prospect of an Arranged Marriage to a rich woman he doesn't love.
- The protagonists of the various versions of Brewster's Millions are these across the course of the stories. They have to spend a ludicrous amount of money in a short amount of time and have nothing material to show for it in order to inherit an even more ludicrous amount of money.
- 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 P. G. Wodehouse protagonist, and most of their friends. Of particular note are Bertie Wooster, his Aunt Dahlia, and the Earl of Emsworth.
- Although Bertie's stories rarely have him in direct contact with the working class, he's shown to be generous whenever the opportunity arises, and he's established as a general tipper. The best example of this is probably in the novel Joy in the Morning, in which Bertie, discovering that it is Jeeves' birthday, insists on buying him a present, which Jeeves informs him is not required or expected. Relenting, Jeeves admits that he would very much appreciate a certain volume of the philosopher Baruch Spinoza, which Bertie somehow assumes is an exciting detective novel. He's also repeatedly shown to have no problem at all with members of his own social class (usually Bingo Little) wanting to marry commoners, which puts him at odds with the more conservative characters.
- Dahlia and Lord Emsworth both own large estates near smaller villages, and are known locally for their great generosity. Dahlia is often involved in community events, such as the fateful distribution of prizes at Market Snodsbury Grammar School in Right Ho, Jeeves, and we see Lord Emsworth's generosity directly in Lord Emsworth and the Girl Friend, where he befriends a pair of schoolchildren on the village Bank Holiday, providing them with a feast of luxurious food and allowing them to pick flowers from his garden, much to the horror of his gardener and his more class-conscious sister Connie.
- Watson Brewer, Kristy's millionaire stepfather, in The Baby-Sitters Club. He 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. And Scrooge had an example in his first employer, Fezziwig.
- Cordelia Naismith in the Vorkosigan Saga. Although it's 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 the 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.
- Harry Potter himself has shown an inclination to be an Uncle Pennybags, especially to Ron — to the latter's chagrin. He actually wishes the Weasleys would let him share more of the money, but knows they wouldn't accept it.
- Robert Asprin's Willard Phule of the Phule's Company novels. Very much a self-made man and Honest Corporate Executive, he uses his copious resources, connections and talent as a high-flying executive to forge the Omega Mob into a coherent fighting force and to keep the brass of the Space Legion off their backs. As a result, he's loved by the men and women under his command.
- Mr. Toad of The Wind in the Willows, although his Upper-Class Twit tendencies and lack of focus sometimes make his company tiresome for his friends.
- Jean Valjean of Les Misérables is incredibly wealthy and uses his wealth to bring prosperity to his town. When he is forced to go on the run, he becomes a loving family man and bequeaths all of his money to his adopted daughter.
- An unusual example is Pippi Longstocking, who's a young girl. Wealthy enough that money doesn't matter, and the most interesting and generous character to be around.
- The Cat Who... Series: When James Qwilleran inherits a couple billion dollars from his mother's best friend in book 5 (The Cat Who Played Brahms), he doesn't have the slightest idea what to do with it. So he sets up a philanthropic fund to assist with various endeavors around the community of Pickax, buys and revamps the dying local newspaper (and recruits his childhood best friend to be its editor), and gets involved with assorted charity activities and events. This generosity, coupled with his likable disposition, quickly endears him to his neighbors and he becomes one of the most beloved figures in the area.
- Old Mr. Laurence, Laurie's grandfather and the Marches' next-door neighbor, in Little Women. While Jo thinks Laurie gave him the idea, after he heard about how the March sisters donated their Christmas breakfast to a poor family, he sends over flowers and ice cream to make it up to them. Beth also tells a story of how she saw him in the fish market. When a poor woman asked the fishmonger for work in exchange for some fish, he refused her, but Mr. Laurence took the first fish he could grab and bought it for her. Later, when Jo and Fritz are saving up to get married and start a school, the narration mentions that he's been longing for an opportunity to help them discreetly and that he likes to pay for underprivileged boys to attend — that way, he gets to both help poor families educate their children, and help Jo by making sure that she gets some of the boys who need her mothering, not just the rich boys whose parents can afford to pay for schooling.
- Trustee from the Toolroom: Sol Hirzhorn. He’s a tough businessman, but quite willing to use his business clout to do right by those he thinks deserve it.
- Bilbo becomes this by the time of The Lord of the Rings, due to having taken a large amount of money home after his quest to Erebor. He spends his money quite freely, gives away lavish gifts on a regular basis, and holds large parties with hundreds of guests. That said, while he's popular amongst a large amount of the Shire, the more graspy and gossipy members hate him for it, partly out of resentment for his open and cheerful attitude and tendency to stir the pot, and partly out of naked jealousy.
- Enforced in Always Coming Home as the Kesh view of wealth is based on generosity, not possessions, and thus the only way to be rich is to give away in excess. When the Kesh woman Stone Telling travels to the city of the Dayao and meets people who are rich by possessions, she's baffled and wonders how you'd even know people are rich if they don't demonstrate their wealth.
- Hilda and Richie: Hilda is one of these. The books imply she is rich as she lives in a Big Fancy House and has servants while the supplementary material confirm indeed she has vast wealth.
- 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 NewsRadio.
- 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.
- The Addams Family: 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 tons of money on everything from supporting a local politician to saving a local swamp from being drained.
Gomez: How much for the suit?
Street Corner Santa: Twenty?
Gomez: All right... twenty thousand dollars.
Santa: Mister, you don't need the suit!
- Jed Clampett of The Beverly Hillbillies could and has given away his fortune to a cause or person he finds worthy without batting an eye, much to Mr. Drysdale's chagrin. He also loves a party and is quite willing to pay for food and entertainment, though typically such falls along his tastes.
- 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.
- Richard Castle, best-selling mystery novelist and unofficial volunteer consultant for the NYPD. 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. This 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 setting a sting for the hired assassin who killed Beckett's mother.
- 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 do (minus the poverty), threw great parties, and never hesitated to give out money to whomever needed it.
- Stewart Babcock, C.C.'s father, is this in the 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 his death 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 to 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.
- Cooper Barrett's Guide to Surviving Life: Cooper's brother, Josh, makes no secret that he is living vicariously through his brother, and is willing to pay for their partying if that's what it takes. This has apparently been going on since they were kids.
Josh: I always have to pay to bail you out. With the TV, and the bar tab, and the time you shot out the window...
Cooper: That was when I was ten.
Josh: And twelve, and fourteen...
Cooper: Okay, fine, but it was Dad's fault for buying me that BB gun in the first place.
- In Billions Bobby Axelrod is this in addition to being a Wealthy Philanthropist. He donates millions to charity but will also gather his old buddies and fly them out to Montreal for the weekend so they can attend a rock concert. If he feels like it, he will order lunch for all his employees from a restaurant in Boston and have it delivered to their New York offices.
- Patrick Jane from The Mentalist got filthy rich during his psychic days scamming people, but he decided to use his wealth for the good to balance it out. He likes giving presents to his colleagues and friends at the bureau — for example, when he wins at the casino in poker, he buys two large sets of jewelry with emeralds and rubies for Lisbon and van Pelt, and he gives very expensive watches to Rigsby and Cho. He also treats them all with dinner and drinks. (The ladies decide to give the jewelry back after the evening, but the guys keep their presents.) One time he gives Lisbon a pony for her birthday.
- It shouldn't be a surprise that the Trope Namer appears in Monopoly.
- 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' daughter and all.
- 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.
- Ted DiBiase Jr's gimmick while in WWE. 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.
- The Ace Attorney character Edgeworth often charters jets so that the impoverished-but-plucky heroes can arrive Just in Time to deliver vital pieces of evidence. Apparently his Heel–Face Turn did not lessen his bank account.
- Mansa Musa of Mali, in the sixth Civilization game, will act this way in the diplomacy screen, fitting with his real life story and civ ability. When sending you a delegation, he will offer you such trifles as indigo cloth, kikeliba tea and one hundred porters carrying sacks of gold dust. Oddly enough, the actual value of the gift he offers is the same as, say, when Teddy Roosevelt offers you apple pie.
- 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).
- Hawke from Dragon Age II. After regaining their family fortune, Hawke is mentioned as using their wealth to improve life for the poor and downtrodden in Kirkwall, double the wages for the miners in the Bone Pit (much to the chagrin of their business partner), fund their Gentleman Adventurer/Lady of Adventure pursuits, and often pay for rounds of drinks down at the Hanged Man.
- Also Varric, as seen in both that game and Dragon Age: Inquisition. He belongs to a wealthy merchant family and uses some of his money to do things like bribe thugs not to harass his friends. By the time of the Trespasser DLC for Inquisition, he has donated so much money to the rebuilding efforts in Kirkwall that his complaint about the lack of a Viscount is interpreted as volunteering, and he's given the job — whether he likes it or not.
- Dragon Quest V: Rodrigo Briscoletti is 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!
- The Dragonborn can potentially become a downplayed variant of this in The Elder Scrolls V: Skyrim. The dungeon crawling can eventually lead to a Money for Nothing scenario, in which your character has literally millions of gold pieces and not enough Money Sinks to eat it all. Money can be contributed to the various temples and given to homeless beggars (there's at least one in every major city), and with the correct perk (Investor, on the Speech tree) you can also invest in most of the businesses throughout the realm. This will still barely put a dent in your fortune, but it's something. Some players have actually gone so far as to devise mods which will allow you to give away more of your money.
- Pearl from Splatoon 2 comes from a very wealthy family and, despite occasionally being rude, is a genuinely friendly and helpful person, as seen in the Octo Expansion where she helps Agent 8 escape the Deepsea Metro.
- 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 their friend Chun Li clothes and jewelry as a gift/payment for her serving as their tour guide, to single-handedly arranging for a massive donation and Red Cross assistance to a remote Indian charity hospital.
- Kalim Al-Asim from Twisted Wonderland comes from a family so rich that he doesn't actually realize just how rich he is. He's perhaps the nicest and most optimistic student at Night Raven College, which Yuu and Grim point out on several occasions. Even the other students make note of how nice he is. Kalim doesn't hesitate to use his wealth on parties, food, and music—all so everyone can have a fun time.
- Shun Akiyama from Yakuza 4 is a Loan Shark by trade, but certainly doesn't act like your typical loan shark; he gives out generous amounts of money (as in, tens of millions of yen) to anyone that comes to him provided they can pass a Secret Test of Character, and charges no interest or collateral for his loans. Heck, most of the time he doesn't even collect his debts and just goes back to handing out money. He's also the owner of a number of clubs and businesses around town, always treats his employees and partners with great respect, and (again) enjoys showering them with free money which he doesn't expect to get back. While it exasperates his secretary Hana to no end and pisses off the other loan sharks in town, Akiyama is just happy to have some success and wants to spread his good fortune to others however he can.
- Ray Smuckles in Achewood.
- Llewellyn the Dragon 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 of.) But it isn't surprising that he's so rich — he owns the patent on fire, and his species secretly rules the world, being behind every conspiracy since recorded history.
- Stasia from Marry Me (Bobby Crosby) is a wealthy celebrity sensation, who also donates a large amount of her money regularly to various charitable organizations, and visits needy places in Africa on a whim.
- In The Inexplicable Adventures of Bob!, Rocko's newfound wealth hasn't 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.
- Mikel Fandango, the king of Quillotia, one of the larger and more prosperous islands in the Archipelago, is a lovable Large Ham and a Reasonable Authority Figure to boot. He gives the protagonists all the help he can, and not only because Tuff and Riley are his maternal cousins, including a large submarine.
- Whateley Universe:
- 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.
- Marcus Vansten from Welcome to Night Vale is rich enough to own every chimney in town, which means a lot in Night Vale. He crosses into this trope after buying his way into becoming an angel and starts donating to local services, such as the bowling alley, and later defeats StrexCorp and the rest of Desert Bluffs by buying them out.
- American Dad!: One of Roger's personas is this and the only one the family likes because he spends so much money to spoil them.
- The Legend of Korra:
- Hiroshi Sato 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. Unfortunately, it's really all to divert suspicion away from him being a member of the Equalists, whom he supports because a Firebender once killed his wife.
- Varrick, like Sato, built his own trading empire single-handedly. While he's much more openly amoral, he's also a charming and affable man who honestly seems to see Team Avatar (particularly Bolin) as friends, even as he's exploiting them for his own ends. Even after they get him arrested for trying to kidnap the President of Republic City, he still seems to honestly like them and holds no hard feelings. Eventually, in Season 4, he ends up becoming an ally after Kuvira decides to implement the Fantastic Nuke he created by accident against his wishes.
- My Little Pony: Friendship Is Magic:
- Fancy Pants, 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 and is even very kind towards the rest of the mane cast despite the latter's boorish behavior, and despite most of the other elite ponies looking down on Ponyville ponies.
- Diamond Tiara's dad, Mr. Filthy Rich. He wears his status on his sleeve, but he's pretty respectful towards Granny Smith because his family owes their success to selling the Smith family's crop in frontier-era Ponyville.
- Cherie in Pop Pixie is very wealthy and quite a bit vain, but she's a nice person to be around in general, frequent mood swings aside.
- The Real Ghostbusters episode "Sticky Business" had Marty Tillis, president of the Stay Puft Marshmallows Company. He asks the Ghostbusters to free the Stay Puft Marshmallow Man from their Containment Unit so he can be filmed in a commercial. The Ghostbusters are initially reluctant to comply, but agree to cooperate after Tillis kindly offers to pay them with the $50,000 needed to keep a children's hospital from shutting down. He even allows the children from the hospital to watch the commercial being filmed.
- Arthur Fortune was a one-episode character on The Simpsons (specifically, the episode "Monty Can't Buy Me Love"). He's exactly like this. He may have been an allusion to Arthur Bach, the titular character of the 1981 movie Arthur (1981) or Real Life adventurous billionaire Richard Branson.
- Stella of Winx Club. She makes it known she's a rich, spoiled princess, but she has no problem sharing the wealth and does not consider commoners beneath her. This is shown as early as episode three, where she drags Bloom on a shopping spree after the latter was sad about not having a dress for the school's dance, and was willing to pay for a very expensive dress (until Flora pointed out this might embarrass Bloom). Note that Bloom didn't ask her to do either of these things.
- The Young Justice (2010) version of Bruce Wayne/Batman isn't fun, by any means, but he operates as this character in the background. Besides taking in Dick Grayson after his parents died and his uncle was paralyzed, he also provides a credit card for Superboy's expenses after he's rescued from the cloning facility and pays the tuition for Artemis to attend the same private school he sends Dick to. Word of God is that he also offered to take in Zatanna after her father was absorbed by Doctor Fate and that he's the third Robin's legal guardian as well.
- 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). NASA is backing him up with the spaceship since they were going to have a five-year gap of not having a ship once they retired the Space Shuttle.
- George Harrison financed Monty Python's Life of Brian out of his own pocket when the studio rejected it, only because he was a fan and friend of the Pythons and wanted to see their next movie.
- Mansa Musa, the Emperor of Mali in the 1300s, was so absurdly rich that even the wealthiest humans on modern Earth have only a fraction of what he once held to his name seven hundred years ago. He was also absurdly generous with his wealth, to the point that he literally threw bags of gold at passers-by while on pilgrimage to Mecca and gave away so much money during the trip that he tanked the value of gold in the world economy for a decade afterward.
- Dolly Parton qualifies for this alongside Wealthy Philanthropist. On top of her numerous business and charities, she also owns and operates her own amusement park, her own water park, her own dinner theater, and her own spa resort to provide jobs and benefits to locals.
- Albert R. Broccoli, who produced the mainline James Bond films, was known for trying to make sure cast and crew enjoyed themselves when shooting on location in exotic locales. When morale was down during the Egypt shoot for The Spy Who Loved Me, he paid for a truckload of treats to be brought all the way from England. Unfortunately, the a lot of the contents were stolen along the way and what was left had spoilt. However, Broccoli saved the day by scrounging for ingredients and serving a massive pasta feast. Also, during the production of The Man with the Golden Gun, the stunt driver meant to perform the famous corkscrew jump was a no-show on the day so another driver, "Bumps" Willard, who happened to be present, hopped in the car and did it flawlessly without any preparation. Broccoli was so impressed and grateful that he ran up to Willard and slapped a fat roll of hundred-dollar bills into the driver's hand.