Despite always being desperate for cash, food or other supplies, some people never seem to actually run out. They might always be desperate for money, but somehow manage to live in the same house for the duration of their show, never getting kicked out once. Or they might always complain about being hungry but never starve. This is even common in works where the characters own a Cool Starship or Humongous Mecha, and somewhat justifiable given that the maintenance, repair and fuel bills on those things have gotta be huge.
Stereotypically, anyPrivate Detective is always broke.
A subtrope of Failure Is the Only Option: Most plots are driven by the characters making a living doing something entertaining to audiences such as catching criminals for money (or maybe being criminals), and if they ever had a windfall they might actually choose to do something less troublesome and therefore less entertaining.
Contrast with Infinite Supplies. Compare Broke Episode. See also Pottery Barn Poor.
The heroes in Outlaw Star continue to get deeper and deeper in debt from the costs of operating, repairing, and re-arming their Cool Ship. Unlike Cowboy Bebop, this never really cuts into their budget for food, because they have a financier who is sweet on Gene and will offer them a job any time they're genuinely strapped.
In Get Backers the title characters are always starving and are frequently denied credit at the Honky Tonk. That still doesn't stop them from being incredibly powerful fighters.
In Urusei Yatsura, Ataru's parents are always struggling to make ends meet, even though Ataru's "wife" is a princess from a highly advanced alien planet (at one point, she casually pays an intergalactic taxi fare which amounts to the value of all the oil on planet Earth).
Ataru's dad regularly worries about how many more payments he needs to make on the house. Not once does the word "foreclosure" ever come up, and at the end of the series he and his family still have their home (despite it being completely destroyed several times).
Lucy in Fairy Tail is always worrying about making the month's rent, despite being the daughter of one of the wealthiest men in the country (she ran away from home) and taking on the most high-paying jobs available (most of the reward money gets swallowed up by the bills for her teammates' property damage).
In Zoids: New Century Zero, the protagonists have a huge mobile base shaped like a giant robot snail, from which they launch their Humongous Mecha, but have trouble scraping together money for repairs.
Can you imagine what the payments are on those things?
This is pretty much said outright in one episode, where an off-the-books scuffle leads to the team withdrawing from the next day's tournament, as replacing enough ammo for Leena to compete with the team would put them below the break-even point even if they got top prize.
Considering that even the design of the thing was ludicrous (More Dakka to the point where Bit was wondering why she didn't stick a few nuclear missiles on it), all those weapons were probaby really expensive, too.
A regular theme in the manga series Lucu Lucu is that the characters are genuinely, and realistically living in poverty for most of the series.
Hell Teacher Nube: Meisuke "Nube-sensei" Nueno often doesn't have enough money even to eat properly, as he is often seen eating a single ramen for one (or two) days. He was outright haunted by the actual God of Poverty once.
It's explained that he could make more riches, but that would involve leaving his work post as a teacher and/or doing either illegal or shady things, which he refuses out of principles. As much, he'll use once or twice his demon hand to cheat at the Pachinko games, where his students can't see him.
Lampshaded by the principal in one episode, when he asked Nube where all his salary went.
Yusuke and his mother Atsuko in YuYu Hakusho. In fact, it's not clear how they pay for the small apartment they live in, since neither of them seems to have a job. The only real hint is an offhanded joke in the seventh chapter that seems to imply that Atsuko moonlights as a prostitute, and late in the manga Yusuke's father briefly appears, suggesting he might help.
In Excel♥Saga, various individuals fit this trope since the manga was poking fun at the recession Japan was going through. But the heroines in particular are always starving since they cannot hold down a temp job. However, their "emergency food ration" survives to the last episode.
This trend is broken in the manga after Hyatt and Elgala become executives of ILL (Il Palazzo's current and most successful world conquest vehicle). Menchi (the aforementioned ration) gains quite a bit of weight because of this.
This development led to brief poverty for Dr. Kabapu and his employees as Il Palazzo revealed his embezzlement and general corruption, but he bounced right back since his secretary Momochi managed to hide most of the money even from himself.
Miyako in Hidamari Sketch fits in this trope. She is generally low on cash, to the level that in one strip, since she didn't even have the 300 yen for lunch, she decided to drink water instead.
This is actually a depressing example of Truth in Television—some people fill their bellies with water when they don't have anything to eat. Of course, this being HidamariSketch, it's more funny and cute than it is sad, especially when Yuno offers to split her lunch, despite losing some of the bread she brought as charcoal erasers to Miyako's hunger.
Lack of funds is a main theme in Binbou Shimai Monogatari—no surprise, since the title translates as "the story of the poor sisters".
Team Rocket in Pokémon are constantly hungry, to the point that they'll offer temporary loyalty to anyone who'll feed them, even Ash and the gang, yet they never seem to starve. They also very often complain of having no money. This is because they always blow their salary on Humongous Mecha in their schemes to steal Pokemon.
On occasion, they have taken regular jobs. But only until they have enough money to pull off whatever scheme they've been concocting.
In one episode they even comment that they never keep any cash more then 24 hours.
In Pokémon Special, Maylene, the Veilstone Gym Leader, is initially jealous of Platinum's wealth and is usually shown to be hungry. At the battle at Mt. Coronet, she outright states that she is poor. This is probably due to the fact that she has a deadbeat dad who does nothing but play slots at the Game Corner all day, much to her chagrin.
The Makino family in Hana Yori Dango. They started out as just comparatively poor, which made sense given that 99.5% of the main cast were ridiculously wealthy, but by the end of the series they were living in a shack, drying seaweed for money.
Train's group in Black Cat are almost always strapped for money, constantly having to take on new sweeps despite managing to catch several bounties worth millions. Apparently their debt tends to be caused by Train breaking things or eating too much.
Ryo-san, the main character of Kochikame, spends all of his money on video games, models, and gambling and is in debt to most of Katsushika (in stark contrast to his two companions at the police station who each have more money than God).
Also Greece. In the CD drama Hetalia Phantasia, he says he suffers from trade deficit and can't play online games because of that.
Claire in Red Garden has trouble with her job and rent, even to the point of her phone line and gas getting shut off, but still manages to make it through.
Most of the cast of Kurosagi Corpse Delivery Service have a problem with this, being university students fresh out of a Buddhist college with no real skills apart from the ones that come in handy in corpse-collecting.
Kobato from Kobato seems to only possess her clothing, her futon and the magical bottle where she stores the suffering of others.
Abel Nightroad in Trinity Blood generally gets very little to eat, to the point of sometimes subsisting on 13 scoops of sugar in his tea. Justified by the fact that he's a priest and has taken a vow of poverty.
Apparently there is no need for money in the Rave Master universe as you never see the main characters working, and tend to spend all their money at the casino. This is very obvious in one episode when they lose ALL their money at the casino and are complaining about being broke while sitting in a first class cabin on a train before going to the food cart for lunch.
Of course, they bought those train tickets before losing their money at the casino. And Elie always wins said money back at every casino (she never even loses once in the manga). There are a couple chapters dedicated to looking for someone to sponsor them, or ways to raise funds. And on occasion you'll catch them being self-sufficient.
A major point in Niea_7 is that Mayuko's troublesome finances get strained even more by Niea's freeloading.
Akihisa Yoshii, the lead of Baka to Test to Shoukanjuu, lives in a state of constant financial woe. It's noted that he frequently prioritizes new video games over his food budget, so it's mostly self-inflicted. He has to eat salt and sugar water for energy, has no hot water, and divides up his meals into 1/64ths so he can survive. His situation improves somewhat after his big sister moves in, but not by much.
The basic premise of Nerima Daikon Brothers is that the eponymous band needs money to build their concert dome, so of course they're always broke to keep the plot going. Ichiro is the most popular host at a host club and does make a good bit of money but saves most of it for the concert dome, Mako is extremely materialistic and tends to blow whatever money she gets, and Hideki is usually the one she gets money from in the first place.
Despite most of the cast being Ojou, Hayate the Combat Butler's Hayate Ayasaki and Yukiji Katsura are pressed to the limits of their pocketbooks continually. Hayate for his selfless giving to his harem, Yukiji for her love of drinking.
The manga series Dai-Tokyo Binbo Sekatsu Manyaru ("Tokyo Poverty Daily Life Manual") revolves around a laid-back main character, Kosuke, who has deliberately chosen to adopt a life of poverty. It's easier that way: you don't need to take care as much stuff, you have less responsibilities, and you can focus on the things that matter like friends and spiritual wholeness. (This could in some ways be a kind of manga manifesto for the freecycle culture.)
Kanba, Shoma and Himari Takakura from Mawaru-Penguindrum live in a run-down house with their penguins and are almost always short of cash. Episode 5 has Kanba discussing matters related to their lack of money with their uncle Ikebe, who is worried about their well-being and how their parents have been gone already for a while; he tells Kanba that he should sell the house and move with his siblings to a smaller apartment, but Kanba refuses to do so. By the end of the episode, however, Kanba has somehow gotten a hold on enough money for the month. This is very important, plot-wise, as we later learn that he's in cahoots with a certain terrorist cell...
The Kunisaki troupe in Kunisaki Izumo No Jijou, despite being a relatively well-respected kabuki house, somehow always seems to be one failed show away from bankruptcy.
The Yorozuya in Gintama are motivated to take all sorts of weird jobs to pay the rent and afford food. Despite constant warnings, they are never evicted.
In A Certain Magical Index, Touma often complains about being low on cash, since he has to pay for Index's meals and for the hospital bills of his battles.
Much to his army's dismay, Eita Touga of 12 Beast cannot resist helping the needy and broke. They are almost always in the red, and considering the size of the army and their composition, it's miraculous he can actually feed them and maintain their gear. Still no victory feasts, though.
Deconstructed at Muteki Kanban Musume: Miki has little money, no TV or video games... because she is The Slacker sponging out his mother. Kayahara Sensei tries to be a Save Our Students teacher who is so depressed that only manages to be The Dreaded among her students... her room is completely empty except for a calendar and a TV she won at a contest. Maybe she has a Limited Wardrobe because her jumpsuit is her only clothes.
Pretty much the entire premise of the Lucky Star spinoff Miyakawa-ke no Kuufuku: the titular sisters are perpetually in poverty because of Otaku older sister Hinata's constant spending and wasteful habits. The end credits song even has them singing about how poor they are.
Variable Geo: Satomi has had to support herself and her brother, Daisuke, ever since their parents died in an automobile accident. But, because of Daisuke's condition and the cost of his medical expenses, she's had to work two jobs and barely makes enough for them to live on. Which is how The Jahana Group manipulates her into joining the VG tournament.
Yuugen Kaisha: No matter how many cases Phantom Quest manages to solve, they stay up to their ears in debt thanks to Ayaka's reckless behavior and excessive spending habits. Each episode ends with Mamoru going over their commisions while deducting the costs of expenses and damage claims filed against them; which always ends with them being worse off than they started.
Durarara!! has Shizuo Heiwajima, who has been fired from several jobs as a result of his Super Strength and (unfortunately) Hair-Trigger Temper. His current job has more toleration for his destructive tendencies, simply taking monetary compensation by deducting his pay (which is presumably a lot considering Shizuo gets angry so easily), yet Shizuo doesn't really seem strapped for cash at any rate. He doesn't even mind the deductions from his pay — if anything, he's surprised that he's paid at all.
Spider-Man is the premier example of this. Despite being a super genius inventor who created a revolutionary new super strong bio-degradable adhesive, friends with several billionaires, married to a model/actress, and being a member of the world's greatest superhero team (the Avengers), he still seems to be utterly broke in most storylines, to the point where he just put up with a dislocated shoulder until it healed to avoid paying the medical bills.
In the Marvel NOW!Avengers relaunch, Tony Stark lures Wolverine, The Falcon, and Spidey back to the team by each offering them something. His offers are respectively: beer, birdseed (sarcastically), and in Peter's case, money. Peter is then shown dramatically hugging Tony while crying "Thank God!"
This is part of José Carioca's character in his Brazilian comic series. He's avoided paying for things so much, his debt collectors have formed their own group known as the A.N.A.C.O.Z.E.C.A. He is not above bathing in a public fountain, or pulling a dine and dash◊. Some of his earlier stories have him balancing this out while also trying to put on the appearance that he's rich (mostly to justify the suit he wore; José wasn't designed with Perpetual Poverty in mind).
In John Kovalic's Dork Tower, Matt and his friends are always short on funds for their hobbies and toys (not to mention the rent), yet somehow manage to stay in the same apartment and drive a car for years.
Donald Duck in any of the DuckTales comics is an even older example than The Simpsons. Somehow, circumstances always conspire to keep him from any riches he may find in the course of the stories.
A running joke, at least in Italian stories, is that Donald puts everything on the tab, and now has an enormous debt to every grocer, vendor, repairman, etc. in Duckburg. Paying off all his debt seems to be a case of Failure Is the Only Option, and his creditors can get downright brutal. Yet he's hardly ever evicted from his big suburbia house. ... Because his landlord is Scrooge. In lieu of rent, Donald does any task Scrooge asks of him, from life-threatening adventures to polishing every coin in the money bin.
Dylan Dog and his assistant Groucho live in a state of Perpetual Poverty.
This seems to be status quo for Old Master Q, where the protagonist of the same name is often seen living on less than meager means. This is doubly true of the first animated film, where he lives in a tiny wooden shack on top of a high rise and running water appears to be his only amenity.
Chester and Deck in Havoc Inc, in part due to Chester's spending habits. When their daughter (something of an economics prodigy apparently) gets into the company books she finds a bill adorned with little skulls.
The Godinez family from Los Miserables, ever since the comic started they are shown living (or as the author said, surviving) below the poverty line: They live in a shack on a landfill and they get their income from re-selling bootleg items they buy from the Chinese. In some story arcs they manage to obtain a large sum of money... only to lose it by some Diabolus ex Machina, or in another they manage to start a business that will lift them from poverty only to be out-competed by the Chinese.
Ghostbusters: The Ghostbusters are never shown to have gained any material benefit from their work. In the first film they start out desperately broke as their business gets off the ground. Even after business starts booming, we never see them spending any money. In the second film, Snap Back causes them to be broke again, as a result of New York City suing them for damages caused by ghosts in the first film.
Most protagonists of fairy tales start out in Perpetual Poverty (because of an Evil Stepmother or whatever) and eventually work their way up the social ladder. Extra credit goes to the poor schlub who thought it was a good idea to worship the god of poverty.
Harry Dresden is always broke in the first several books. Magic doesn't pay well. Even later on, when he gets a job with the Wardens that makes a decent amount of money, he stays in the same grotty little apartment and keeps the same run-down car - both because he's still far from rich, and because magic's tendency to mess with technology means that he doesn't get along too well with electricity (e.g.: icebox rather than freezer) much less anything more complex. (And because his landlady is remarkably understanding about things like zombies trying to break down his doors, and because Harry's not that big on change.)
In Skin Game, Harry takes part in a heist, where he is promised two million dollars upon completion, plus whatever he can grab from the vault and stuff in a bag (which is estimated to be about twenty million, if he's smart and grabs gems). He doesn't get paid or even get a bag, but one of the other survivors was smart enough to fill her backpack with diamonds. Harry gets one-fifth, which, assuming the estimate was correct, is four million dollars. Though he gives half of it to Murphy.
Source and Shield Pairs in the Hero Series are subsidized by the government. They aren't paid for their work, but get free housing, and by law all merchants are supposed to give them whatever they want when they ask for it. On a social level, this isn't nearly as good as it sounds when everyone resents you for walking into their bar and getting free drinks.
In The Name of the Wind, a major part of the story is Kvothe's constant struggling with his complete lack of money. The close narration makes it possible to follow exactly how much money he has at any point in time. Any time he pulls off some ridiculous feat to scrounge a few extra coins, they go straight to paying off his debt to the friendly neighborhood Loan Shark. His money problems are mostly resolved after he returns from his trip in The Wise Man's Fear.
The Weasley family in Harry Potter, whose wands, books and robes have been handed down through seven children in order to save money. Despite this, the Weasleys have no problem letting Harry and Hermione (both well-off) stay with them for all or part of the summer. They even manage to hold on to their Perpetual Poverty despite winning the lottery in Prisoner of Azkaban. Rather than buy new robes, they opted to blow the lot on a trip to Egypt. This could be simply because the Weasleys feel that a family trip is more important than material possessions, though; and it was the first time they'd seen Bill, who worked there as a curse-breaker, in years.
The Weasleys' situation never seems to improve, even after the five oldest children move out. Although once the Weasley twins receive seed money from Harry at the end of Goblet of Fire, they become wealthy in short order (and all the Weasley siblings become very successful in their chosen fields, even if those fields don't always pay well.)
Remus Lupin is always described as thin and shabby looking, because no wizard will employ a werewolf and between transformations he's often ill or injured. There is no indication that his two very wealthy childhood friends helped him out after graduation, and Sirius doesn't leave him a cent in his will, instead bestowing his family fortune on Harry (who was already more than comfortably well off).
In the Dirk Gently series, Dirk lives the stereotypically broke life of the Private Detective, all the more so because karma has apparently latched on to him and decided that no matter how many mysteries he successfully solves, none of his clients will ever pay him.
Fafhrd and the Gray Mouser tend to go on epic benders whenever they come into any loot, and most of their stories begin with them flat broke and either monumentally hungover, on the run from creditors, or both.
The Young Ones are prey to the oddest swings of fortune: they complain of hunger, but never run out of lentils (which, admittedly, only one of them actually likes); they wind up burning all their furniture for fuel at one point, but suffer an unlikely windfall shortly thereafter; and, indeed, they never get kicked out of their lodgings until the last episode of the series.
Firefly's crew is usually struggling to make ends meet, even keep their ship flying, on top of their higher goals. At one point, Mal actually manages to sell something without shenanigans going down... and then you see the laser sight on his buyer's forehead...
The tabletop game based on the series actually added a negative character trait that enabled players to roleplay this; taking it meant that there was something like a one-in-four chance that the character would lose all the money they were supposed to be getting paid at the end of a quest. It was named after Mal's catchphrase, "It Never Runs Smooth".
There were a few episodes following a heist where they stole a few hundred pounds of pharmaceuticals in which they could afford fresh fruit. But they spent it all, quite a bit of it on ransom in the episode mentioned above.
Even more the case in Farscape, who for long periods had no higher goals other than finding a way to get enough to eat to stay alive and avoiding capture. They knock over a bank in the climax of the second season, however, which eases most (but not all) of their money troubles.
Not quite as severe day to day (but with a worse overall situation given the population difference) was Battlestar Galactica, which also included several episodes attempting to get enough food, water and fuel to keep surviving. The ships were constantly getting more damaged and even the clothes getting worn out, and even when they had enough supplies to get by it was still eking out a miserable existence in rooms the size of closets (if you were lucky enough to get a room — very few did even among the senior crew, Admiral Adama being a notable exception) with nothing much to relieve the crushing monotony and basic nature of their lives, eating algae processed muck as a staple. It comes as no surprise they always made sure they had plenty of booze around. Much like the students' example in the trope explanation.
This was also the case, though less emphasized, in the original; at least two episodes revolved entirely around getting new seed, or supplies of fuel, and a segment of "War of the Gods" showed just how low living standards are for most of the Fleet's population.
Practically every character living in the neighborhood in El Chavo del ocho, with the possible exception of Dońa Florinda, judging by her house, her solvency, and the little greasy restaurant she owns later in the series (Still, one could ask why, given her snobbishness, she couldn't move to a better place).
Don Ramón being the most proeminent example, so much it's a Running Gag having his landlord, Sr. Barriga, charge him from his 14 months due of rent.
Justified by the Bundy Curse, which keeps Al alive only to suffer. No, Really.
Al even gets sent to Hell in one episode, but he's so thrilled to be away from his family that no matter what torture Satan enacts, it's still an improvement over his normal life. Naturally, Satan eventually figures out the one thing that could bring him eternal anguish: return him to his home and preserve the status quo.
Private detective Seiji Hayami from Cutie Honey THE LIVE fits this trope to a tee. He claims to be living in poverty as a way to infiltrate the underworld of Japan... whether or not that can be believed when you consider his luck with clients and general ineptness at his job is up to the viewer.
Honestly, how would Magnum survive without the good graces of Robin Masters and the loyalty, gullibility and infinite patience of his friends?
A major theme of The Honeymooners. Both Ralph and Norton have steady blue-collar jobs, but Ralph is constantly throwing away their wages on foolish get-rich-quick schemes. And there's an infamous episode where he quits, and the situation isn't rectified by the end of the show.
While not impoverished, one can understand why she may feel she is, since she's best friends with a hotel heiress, one who constantly remarks how poor she is, at that.
The main family in Malcolm in the Middle. There are several episodes throughout the show that emphasizes how much they are struggling to make money and support their four, dysfunctional children. The fifth and oldest goes through this as well, but subverted in that he constantly travels around trying to make ends meet. Justified as neither Hal or Lois earn very much (he's an average blue-collar office worker, and she works in convenience store) and providing for 4 (then 5) children and sending Francis to military school costs a lot.
The parents frequently engaged in actively destructive behavior that kept them in poverty, and the father admitted as they sabotaged Malcolm's attempts to get away to a school in Europe that the financial benefit of his being gone didn't matter to them as much as keeping him around to fix the problems that their on self-destructive behavior caused.
Jim Rockford of The Rockford Files fits the stereotype of the perpetually broke Private Detective. While he does have many successful cases, the various methods that his clients use to avoid paying him is one of the show's Running Gags.
For The Monkees, there's often a threat of running out of food or being kicked out of the beach house for non-payment of rent, but the status quo is maintained.
The main characters of Scrubs often complain about being short on money. Despite being doctors. The only one who never seems to have any money trouble is the janitor.
This is more an issue in the early seasons when they're interns and residents (a clear case of Truth in Television; any real-life doctor has spent their education and the early years of their careers as the hospital's Butt Monkey). When they finish their residencies, money doesn't seem to be an issue nearly as much.
Penny from The Big Bang Theory is a waitress who is struggling to be an actress, but only getting in a few plays. She complains about being poor, yet somehow can afford living in a single bedroom apartment and keeping an impressive collection of clothes, given a new outfit of hers every episode. She also freeloads off her neighbors.
Stuart is also said to be so poor as to be living in his own store.
Frank, however, is explicitly very well off and is stated or implied to have bailed Dennis and Dee out of trouble on more than one occasion.
The main cast in Only Fools and Horses seem to be just a few days/weeks from failing to pay rent and ending up evicted. The episodes with the poker game and the psychic reading one come to mind here, since it's mentioned in universe how everyone's pretty much completely skint. Somehow the Trotters still don't run out of money for food or other essential items, or get thrown out.
Max on Happy Endings switches between jobs frequently, though most of the time he doesn't have one at all. He inadvertently reveals that Dave, who had moved in with him, was deceived into paying all of the rent while he believed he was only paying half. One episode revealed he did things like go to various support groups for the free food.
Joey from Friends would fall squarely into the trope if it wasn't for his friend and roommate, Chandler. Joey is an actor that goes from gig to gig, so the pay isn't very high or stable while Chandler has a steady and well paying job in an office. Despite how desperate for money Joey needs to get by, he refuses to accept money from Chandler directly, believing that he shouldn't borrow money from a friend.
In Noob, the player behind Gaea and the Noob guild itself. Gaea has a few schemes going on to make extra money, but she loops back into being a Starving Student between her investements into the MMORPG everyone is playing and Crack is Cheaper (just check out that bookcase in her living room). The Noob guild is in that situation partly due to Gaea (who is The Scrooge in-game) always finding a excuse to not contribute to its fund.
In the webseries, when they do have game currency to spare, their Psycho for HireHonorary True Companion suddenly remembers that she's a mercenary and wants to get payed for that dungeon run she joined on her own initiative (unsuprisingly, she's Gaea's best friend and roommate).
In the novels and comic, it turns out that Omega Zell and Sparadrap aren't contributing that much either. Sparadrap uses his spare income on his pet collection and Omega Zell got Arthéon to delay the arrival of a potential new recruit he didn't like for a year in exchange for a steady contribution to the guild's fund during said year.
Many songs are about families or couples who struggle to survive but never go completely broke, mainly because they depend on each other. Examples:
Andy Capp lives off his wife's wages and is usually behind on the rent. He is occasionally evicted, but always gets his home back so that the neighbours (Chalky and Ruby) and rent collector (Percy) are always the same.
The Lives Of Harry Lime: If Harry every succeeded in one of his get rich quick schemes, he would lose all of the money by the end of the episode.
On Cabin Pressure, MJN Air is always about to go under due to lack of resources. The plot usually revolves around A Simple Plan to keep the company open.
Genius The Transgression has this as a rapidly increasing problem for Geniuses: mad science is expensive, time-consuming and difficult to make a profit on. One of the few remaining advantages Lemuria has is a lot of money and weird science supplies.
Fortunately for most Geniuses, there are workarounds: a Merit that makes mad science cheaper, working in sane technical fields or education, building giant robots and robbing banks with them...
This is usually the flavor of most Shadowrun groups. The Runners are either completely broke or are cheated out of their money by the corporation they're hired by, or blow all of their money buying guns, cybernetics, and the like.
In GURPS characters with the Dead Broke disadvantage will always lose any money they get.
An unlucky crew in Traveller can easily end up in this situation despite transporting cargoes that can be worth millions of credits considering mortgage payments on the ship, plus maintenance, life support, and the necessity of having enough left over to buy the next cargo.
An especially egregious example of this trope is found in Warhammer Fantasy Roleplay, seeing as the 2nd edition of the game, as it got more and more supplements, got exact prices on every damn expensive thing the creators could think of. The most expensive object in the game would be a best craftsmanship galleon, which following game rules costs a stunning 120 THOUSAND gold crowns in a game where players have much better odds scavenging their equipment than working to make enough money to actually afford pistols or plate armour - both of which at common craftsmanship cost almost 1/500 of the galleon. Yeah... it's basically just a Take That to players.
Reign encourages players to do this to themselves by offering bonus Experience Points for squandering your wealth, in the style of the Fafhrd and the Gray Mouser stories mentioned above. The effect is somewhat diminished once your Company has much of any Treasure score (which might be right at the start) and you can easily meet all your personal needs out of the petty cash, though. Then again, Game Masters are advised to keep note of that practice and penalize the Treasure score if done too much, meaning you could potentially set a whole town, business, or kingdom into this trope through overindulgence in frivolities.
Detective Dick Gumshoe, although not a private eye, fits the trope and is constantly taking cuts to his police salary. At one point, he mentions that he can no longer afford ramen. It is hinted though, that Edgeworth rewards his moments of competence handsomely and would never let him become too broke.
Phoenix doesn't do much better, to the point where it's a Running Gag he gets made to foot the bill for everyone else. Then again, pretty much every other client of his is wealthy to some degree and probably reward him generously.
The whole village of Kurain, once prosperous and in high regard across the country, seems to suffer from this nowdays, to the point of the Fey family keeping a "sacred" scroll entitled "Hundred-and-X ways to save money". ("X" because the list is continously expanding.) It explains how Maya, the daughter of the Master and thus pretty much the Princess of the village, is addicted to Junk Food.
Phoenix and Trucy live on very little in Apollo Justice: Ace Attorney after Phoenix gets disbarred. Although Trucy has apparently been the major breadwinner for years, there are hints that this isn't quite so.
Robot Alchemic Drive features Nanao, an impoverished Japanese high school student. One "episode" of the game gives you her delicious recipe for "water soup": Water, oil, and bread.
Sam and Max are shown as living in perpetual poverty conditions despite Max becoming the President of the United States, explicitly moving the Oval Office to their familiar squalor.
It goes so far as to his choice of pet - look up the market price for Scottish Fold kittens one of these days.
And in the sequel it's revealed that at one point he commissioned a full scale and fully functional replica of a Humongous Mecha from one of his favorite animes. Granted, it turned out to be useful but still...
This is actually averted in canon, though. She still doesn't get donations, but she's never been shown to lack for anything she needs or wants, and she's only gone as far as unsubtly hinting at people to donate once or twice. Supposedly she gets some income from youkai hunting and incident resolution.
Reimu's main problem is her work ethic, not that she doesn't do her job, but she does it wrong. Her job description is youkai extermination, and lots of humans aren't particularly happy that she just befriends them instead, meaning she gets less donations than she might like.
Gabriel Knight is shown as being rather poor - at least in the first game; where he pretty much sells a family heirloom to make $100 and get past a specific plot point. He does manage to afford flights to Germany, West Africa, and back mostly because he charged them all to Mosley's credit card. In the sequel, a book deal and some loot from the Voodoo syndicate base has given him the means to move to Germany and live in the family castle.
Thief: Garrett, despite looting ludicrous amounts of gold, trinkets, and artifacts, seems to still be dirt poor and is constantly worried about paying the rent. His fence must be stiffing him.
Team Fortress 2's Soldier has always suffered some form of this trope. He was first shown to be a sort of Crazy Survivalist, living in a run-down, windowless, unlit apartment, surviving on army-surplus soup and ribs. While he later gains a roommate (in the form of the wizard that caused the events of Monoculus and DeGroot Keep), he has a hilariously 'real' cheap children's-style Halloween costume made of discarded trash, while the other eight classes all have high-quality outfits (in-universe). He is then apparently kicked out of his apartment by his wizard roommate, as the Pyromania update has cast the Soldier as a crazyhobo who is reduced to cobbling his armor and weapons out of junk and garbage. He also believes that his Tinfoil Hat will keep people from stealing his thoughts and is reduced eating expired army-surplus soup from dented, rusty cans he wears as grenades. Given the nature of Team Fortress 2's setting and the Soldier's notably deranged, moronic personality, this is all Played for Laughs.
In The Wizard Of Oz Beyond The Yellow Brick Road, you don't obtain coins from battling enemies. You obtain them by finding them lying around the areas you explore. There are never more than 3 or 4 on the same path, meaning coins are in low quantity. If you buy any items, ever, you'll be perpetually broke.
Ragna from Blazblue tends to be this as so long as the meal is free, he won't refuse.
He's a wanted man. His opportunities for making money are limited, establishments that would take it without calling authorities even more so, and people and places sympathetic enough to harbor him generally have the goodwill to feed him as well.
Yayoi Takatsuki from The Idolmaster is easily the least well-off of all the idols. This is due to her parents' insufficient income combined with the amount of children they must support (Yayoi is the oldest out of six). The status of 765Pro as a relatively small agency also means that Yayoi's income isn't all that big either, and she is perpetually doing domestic jobs in the office for chump change. She even borrows small amounts of money off the Producer occasionally.
The cast of Sluggy Freelance are broke almost enough to be in perpetual poverty.
Around 2003, this poverty was maintained in part because (a) more than half the cast refused to seek jobs and (b) Gwynn, who had actually made a godly amount of money last Halloween, kept the profits secret from the rest of the gang.
As of December 2008, Torg's and Aylee's funds gained by the collapse of HeretiCorp were unfrozen. They are now millionaires (likely to be nullified by fraud, theft, or having to pay for collateral damage).
Harold and Clancy from +EV win millions in poker, but shit it all away.
In Three Jaguars, Business Manager is afraid of this, ending in starvation.
Everyone in Dork Tower save Ken is generally short on funds, although they're usually able to salvage the rent from somewhere (usually via procedures that may or may not involve selling blood plasma) after Igor steals it. Ken, at least, has a steady job and has occasionally offered to spot Matt the rent money in an emergency.
Jade Sinclair of the Whateley Universe runs away from an abusive father, is staying at school on a scholarship, and cleans the school sewers (amongst other maintenance tasks) for the little money she can scrape together — and then spends it on weaponry, defense systems, upgrading her "sister", and maintaining her cover story. She is regularly unable to afford things like more or better clothes, and refuses anything which smacks of charity. Her obscenely rich teammate has to resort to all kinds of subterfuge to reduce Jade's costs and/or get her to accept the occasional gift. It also doesn't help that she's dating someone who has several dozen million dollars to throw around, but she will still only accept very personal and at least psuedo-romantic tokens of affection. As a result, she owns at least two nearly priceless mithril-based artifacts, several (dozen?) thousand dollars in custom precision-worked superhero devices, materials, and uniforms, and a casual-wear selection of clothes that hobos would consider sparse.
Vork of The Guild is able to keep his house only by continuing to recieve his dead grandfather's Social Security check. He steals his Wi-Fi connection from a senile neighbor and raises pigeons (excuse me, squab!) for food.
The Diresoldiers guild have to constantly freelance work just to get by with their pathetic budget. It doesn't help that they can't steal electricity from a zoo anymore to power their HQ, but the polar bear habitat was starting to look like an exhibit on global warming.
Viciously deconstructed in John Cheese's Cracked article "5 Things Nobody Tells You About Being Poor" in which he outlines just how insanely hard escaping from poverty is and how there are almost endless landmines in the process that prevents people from ever escaping it.
Kenny McCormick of South Park is impoverished to the point of eating frozen waffles and bread sandwiches on a regular basis.
Yet somehow, they are able to afford a halfway decent computer and a World of Warcraft subscription.
And a brand new PSP!
And a freaking Xbox One during Black Friday.
Dr. Zoidberg on Futurama is always poor, hungry, and lonely. Something of a Belated Backstory, as he was none of these things in the first season.
When told most doctors are, in fact, rich, he refuses to believe it.
Although his poverty is at least partly because he is very bad with money, and he doesn't have too much trouble with food as he can eat practically anything.
The Simpsons are repeatedly said to be always strapped for cash and having to use sub-standard food. They also have a giant house, two cars, and always seem to have money in their savings for Homer to spend to get the family into trouble.
Of course, there have been some instances where Marge has been shown to secretly be thrifty so that when Homer does do something stupid, they can bail him out. Sub-standard food is apparently the trade off for a happy ending. She also has been shown to secretly buy regular meat instead of Veggie Meat for Lisa and trick her into eating it, as the Veggie Meat is more expensive.
Apparently, Marge also pads Homer's meatloaf out with sawdust. Sawdust.
Their need to scrimp on one occasion became so great that one night of the week became "chub night".note Chub is a type of fish which at the time was inexpensive.
And they (usually Homer) manage to suddenly get rich and poor again at such a regularity that it's lampshaded, surely they have some money left over.
Homer constantly stealing things from Ned Flanders may be motivated in part by this.
Played straight in Homers Enemy when Frank Grimes is shown to be incensed that a buffoon like Homer can skate by in life and still afford better food, a bigger house and 2 cars, whereas the hard-working Grimes has nothing to show for it except "this briefcase and this haircut!".
Though according to Grimes' son, "he liked hookers." If Homer ever had to pay for sex, it was because Marge was padding out the "Homer Was Stupid Again" fund.
The Two Homeless Orphans are constantly on their last dollar (which they then gave to the Simpsons when they thought the Simpson Christmas had been ruined).
Depending on the story in Ren and Stimpy, the duo are usually portrayed as poor and homeless trying to find a home or food, while other episodes depict them as living together in a house and are relatively well off.
Other episodes depicted them as married to Slavic ladies and living in Yugoslavia, so take that as you will.
Chester McBadbat on The Fairly Oddparents is shown to live in a trailer, has to reuse paper plates, and has mentioned eating out of the garbage. Despite this, he seems to afford a few frivolities.
It seems most of his money goes to his dentist who in turn gives him free passes to the local skateboard grounds where he injures his teeth severely.
Bob of Bob's Burgers never seems to make any money off his business, and has stated that he's never actually paid his landlord rent on time. The fact that they continue to be forgiven on missing payments is odd considering their landlord is so greedy he tears nuts and bolts out of roller coasters while people are still on them.
It was explained away in a season one episode: Mister Ficheoder is incredibly eccentric, and he is much more lenient with Bob's rent because he reminds him of his father, and because he considers Bob more interested in creating food than making money; "A Beef-artist! A Befartist! You're like a greasy, heterosexual Walt Whitman!"
Family Guy shows the family occasionally cutting back on spending and have at least lost their house to their debt once (Peter had gone through several jobs before finally landing a stable job as a shipping clerk at a brewery, which doesn't pay too well), but the family is seen with two cars a nice sized house with a backyard and four bedrooms despite whatever money problems that hound them from time to time. While Peter's job doesn't pay a lot, it's implied that Lois may borrow money from her rich parents whenever things get tough.
At one point in "Hanna Banana" when Chris is showing a video to try and prove the Evil Money's existence, among other things shown is Lois stealing from Chris' wallet, showing that the the Griffins might not be able to really financially support each other.
Hanna-Barbera's Lippy the Lion and Hardy Har Har seek their fortune time and again, and never attain it.
H-B's Top Cat uses conniving and hucksterism to keep his gang fed in an otherwise impoverished organization.
J. Michael Straczynski claimed that this was part of why The Real Ghostbusters is so funny—they're a world-famous ghost-hunting team, yet they're always just teetering on the edge of bankruptcy.