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- Brainy Smurf wears one in The Gambler Smurfs after losing everything at gambling (even his glasses).
- In Carl Barks' "Statuesque Spendthrifts", Uncle Scrooge competes with maharaja of Howdoyoustan about who can raise the biggest statue of Cornelius Coot, which to the latter ends with this trope.
- In the album "De fez van Fes" of the Belgium comic book series De Kiekeboes, we twice see a man in a barrel; one is walking out of a tax office and the other out of a casino.
- In the Lucky Luke book The Daltons Escape, Luke runs into a man in such attire. The man explains that he was transporting a tequila barrel on donkeyback and the Dalton robbed him of everything, including the tequila (which they drank) and the donkey (which they ate).
- Jose Carioca (or Ze Carioca) once became invisible in order to manipulate a soccer game so he'd win the lottery. (There's one lottery in Brazil where people bet in the results of a series of soccer games) Because his clothes didn't become invisible, he took them off and went to the field. The invisibility potion wore off while he was at the field. Wearing nothing but a barrel, Zé was seeking revenge against the witch who sold him the potion and the guardian devil who goaded him into seeking her help.
- The page image for Gone Swimming, Clothes Stolen shows Captain Marvel in one, which really raises more questions than it answers.
- Disney Ducks Comic Universe: Used in a more recent Scrooge McDuck story where Scrooge and his nephews travel into the future to sell some items which they believe might be rare and valuable then. It works well enough but then they miss their window to return to the present and have to wait 24 hours in the future for the next window, which is when they learn how much things really cost in the future due to inflation. By the time their time window opens again, they've had to not only spend all the money they made, but also sell some of their clothing, wearing barrels instead.
- In "Stitch Pitch" in Mad House Comic Digest #5 superhero Mighty Inch is shown standing on the counter wearing the world's smallest barrel while the tailor who's the subject of the story is making him a new costume.
- Black Moon Chronicles: After Wismerhill and Pile-ou-Face rob a merchant, they leave him with only a barrel.
- Appeared in one short Dilbert arc. "Our new dress code is barrels." The impracticalities of wearing a giant stiff tube of wood are explored for comedy such as them sliding up when sitting down.
- Long ago, Popeye managed to beat the Sea Hag at gambling so badly she ended up wearing one of these.
- Hägar the Horrible's looting sometimes results in the castle owners wearing barrels.
- An old Donald Duck daily strip contained a "lost clothes" example. In the first panel, one of Donald's nephews is shown coming home from school wearing a small barrel and looking embarrassed. The remaining panels show Donald going to the school with a ladder and retrieving the nephew's gym shorts from the top of a pole vault bar.
- The character "Uno Who", an elderly man who wears a beat-up barrel, who appeared in editorial comics. He usually represents the hard-done-by taxpayer.
- The very first issue of German politics magazine "DER SPIEGEL" contains a cartoon where (symbolic) Germany wears a barrel. Since it appeared almostnote directly after WWII, a very justified depiction.
Films — Live-Action
- Although no one wears it, there is the barrel in the neighbourhood of El Chavo del ocho where the titular Chavo seems to reside. Quico did once, because Don Ramón was wearing Quico's clothes.
- Quentin on Welcher And Welcher expressed disapproval at the fact that this wasn't seen anymore, describing it as a very funny image.
- Mentioned in an episode of Seinfeld. Elaine finds out the man she's dating is poor, and Jerry asks, "Does he wear the barrel with the straps?"
- Saturday Night Live (which can be like a living cartoon at times) had this on a Weekend Update segment where Lehman Bros. CEO Richard Fuld (played by Jason Sudeikis) comes out wearing a barrel because his company was the first to go under because of the 2008 economic crisis. Lampshaded when Fuld explains that he can't sit down because he's wearing a barrel.
- Ross and Moose end up wearing these during the You Can't Do That on Television episode about theft, when their clothes (and most of the set) have been stolen. Moose's has still has water, and a rubber duck, in it.
- A part of Brazilian game show named Topa Tudo por Dinheiro ("Agree to Everything for Money") consisted of an employee making an unusual proposition to a random person and the contestant had to guess if the random person would accept for less than a certain amount of money; for that amount or more; or not accept at all. At least one occasion had the random person was offered to exchange his/her pants for a barrel and some cash.
- Horrible Histories's version of Diogenes, much like the Real Life one, lives naked and penniless in a barrel.
- Maude: Walter uses this trope during a Kitschy Local Commercial advertising the low prices at his store. Maude is shocked and humiliated that her husband would parade himself around like that.
- On The Ricky Gervais Show, Ricky and Steve pictured Karl going to school in one of these as a child.
- There was a fairly popular early 1990s Dungeons & Dragons supplement called The Book of Marvelous Magic, which contained a cursed item called a Barrel of Poverty. The first person to look inside of it would have all of his personal items, including all clothing, weapons, armor and even spell components, magically transported back to his home, wherever that was. The Barrel would then become non-magical, but would grow straps to allow the now naked adventurer to wear it to avoid embarrassment and because it was slightly better than no armor at all.
- The "Stripped" consequence, which discards all the player's Trick cards, in Kitsune: Of Foxes and Fools shows Cori wearing one.
- In Sierra's Jones In The Fast Lane, failing to buy new clothes for one of your character every once in a while will eventually cause the character to resort to wearing a barrel. Others walk around using censor bars.
- Also in a Sierra game, the first Leisure Suit Larry featured a broke guy with just a barrel and an apple he'll sell for 10 bucks. You'll need to buy it. (The guy in question is implied to be Apple's Steve Wozniak).
- There is a gambler in Jak and Daxter: The Precursor Legacy who lost all his winnings. For some orbs to get him back on his feet he'll hand over your Plot Coupons. Mild degrees of discomfort can result when he hands you the coupon he's keeping inside the barrel.
- SpongeBob SquarePants: Legend of the Lost Spatula for the Game Boy Color includes a mission where SpongeBob [the player] has to help Patrick find his lost shorts. Patrick is seen wearing a pink barrel and looking very sad.
- One of the sponsors for the Wrong Answer of the Game in the 2011 release of You Don't Know Jack is "Fashion Barrel", a chain of stores that sells wearable barrels.
- The main character in the freeware game Nonsense Madness wears a barrel, for no other reason than to amplify the nonsense.
- This is one of your first equipment sets in Half-Minute Hero, reflecting how your character is being fleeced for all his money by his hyper-capitalistic Goddess. Other characters remark it makes him look poor.
- In Kevin & Kell, when Kell's mother Elanor loses her life savings day-trading, she suddenly goes from wearing a coat composed of live minks to wearing a barrel.
- In The Princess Planet, Princess Christi and her snowman friend briefly wear barrels after losing at Strip Poker, but Christi later has to cover her nudity with leaves.
- After making one too many cross-dresser jokes in the Cross Time Cafe, Tarin the fox wears a rain-barrel after he gets skinned alive and his fur made into a David Crockett-style hat!
- This Nobody Scores! zig-zags the trope. Jane Doe arrives wearing a barrel, probably in poverty, but really happy and with a protege - also in a barrel and holding a hypodermic needle.
- In an early strip of Adventurers!, Karn wears a barrel after all of his equipment (including his clothes) is stolen by Drecker.
- Worn by Gertrude & Brunhilda in The KA Mics.
- DuckTales: Vacation Vanhonk is seen wearing one in "Sir Gyro de Gearloose". Not because he's broke, but because the automatic dressing machine Gyro built for his only dresses itself . . . and presumably won't let Vanhonk wear any of his clothes either!
- Referenced in the opening theme to Freakazoid!; the lyrics "So stay tuned to this station / If not, we'll be unemployed" is accompanied by several characters from the show wearing barrels.
- In the Futurama episode "Raging Bender", one of the robots Bender fights as part of his stint as an Ultimate Robot Fighter is a rich-looking robot. Bender seals his victory by forcing a barrel onto him labeled "very poor".
- In Harvey Birdman, Attorney at Law, Harvey is called out of court by Gigi to buy her things. After a shopping montage, he returns to the court wearing a barrel.
- In the first part of the Chip 'n Dale Rescue Rangers pilot, main villain Aldrin Klordane's lackey Percy is seen wearing a cardboard box in this fashion, not because he's flat broke, but because the police dog Plato tore off the bottom of his pants.
- Subverted in an old Goofy cartoon, "Get Rich Quick": After playing dice, Goofy is seen wearing a barrel, holding it up with both hands. He then hails a taxicab and, in a brilliant subversion, empties the barrel — full to the brim with his winnings — into it.
- In the TDA special of Total Drama Island, DJ and his mother are both seen wearing these after countless lawsuits leave them broke and homeless.
- Happens to Reggie van Dough in an episode of Hanna-Barbera's Richie Rich when Richie thought that his father had lost his fortune, as part of his friends helping to earn his money back, Reggie starts selling Richie's goods at absurdly low prices; when he is discovered, the mob strips off Reggie's clothing, forcing him to run off wearing only a barrel.
- A Garfield and Friends episode depicting Garfield's take on the Arabian Nights had Jon playing the part of a young artisan with Garfield as "Alley Katta" in a town overrun by thieves. At the start, Jon went out to get a job with the Sultan declaring that "I have nothing left to lose" and, of course, ran back in the room a second later wearing a barrel. Garfield commented that "we'd better jump the story ahead before someone steals the barrel." (Jon got his clothes back in the next shot.)
- Schoolhouse Rock had this happen to the colonists when they were unfairly taxed in the episode "No More Kings".
- A non-finance-based variation comes at the end of the Tom and Jerry short "Love That Pup'", when Tom is shown donning one of these after Spike the bulldog follows through on a threat to skin him alive.
- The Merrie Melodies cartoon "Hollywood Steps Out" features this trope near the end when Harpo Marx uses a slingshot to pop Sally Rand's balloon. She wasn't poor; it was for decency reasons (she was performing a nude bubble dance and the Hays Office would have banned the short outright if she was shown naked after the bubble popped. Plus, it's just funnier this way).
- Used in this old Sesame Street cartoon short.
- After Doug finds an envelope of money and has it legally declared his, he learns it belonged to an old lady and is conflicted over what to do. In his Imagine Spot not only is the lady in a barrel, but her dog as well.
- Drakken wears one in Kim Possible episode "Showdown at the Crooked D".
- In the Looney Tunes short "My Bunny Lies Over the Sea", Bugs Bunny meets a Scotsman wearing a kilt and quickly outfits him with a barrel to cover his "indecency".
- In another one, Daffy was hunting a bear when an explosion made him lose his feathers. Fortunately he had them numbered for emergencies. Unfortunately, he only recovered the ones from the upper part of his body. The bear made a headdress from the others. Daffy put on a barrel and went after the bear when the game warden stopped him because hunting season was now closed. Daffy then announced they hadn't seen the end of him and started to leave, when a part of the barrel fell down, revealing "his end". Daffy doesn't seem to have noticed it.
- Adventures of Sonic the Hedgehog had several anthropomorphic sheep losing everything (including their freedom) to Robotnik in rigged gambling. Once they lost their wool, they were given barrels. Robotnik's casino even had nickel alleys that automatically removed the wool and gave the barrells.
- Pink Panther once shaved all his fur to rid himself of a flea. He then put on a barrel.
- In one Popeye short where he and Olive were about to get married, Bluto sabotaged Popeye's preparations, leaving our hero with no choice but showing up wearing a barrel, causing Olive to reject him and agree to marry Bluto. Popeye got his revenge by disguising himself as Justice of Peace and reminding Bluto of the duties married men usually have to follow, causing Bluto to run away from the marriage.
- Woody Woodpecker: Buzz Buzzard was once running a supermarket where a customer entered with a barrelful of money and left wearing the barrel and carrying a small piece of meat.
- In the 1920s Felix the Cat cartoon "Felix In the Swim", Felix and his friend, a young boy, go swimming together. Their clothes get eaten by a goat, so they have to go home in barrels. (This creates some Fridge Logic, since when they originally went in they were wearing swim trunks. And, wait a minute, Felix wasn't wearing any clothes in the first place...)
- The Smurfs:
- A debt collector once took all the furniture from Gargamel's house and left him nothing but a barrel to wear. When Gargamel protested about being left like that, he said he'd come back later to take the barrel.
- In another carton, some Smurfs wore barrels while waiting for Tailor Smurf to make new pants. (They had escaped Gargamel's glue trap by leaving them behind; why barrels instead of towels? It's funnier!)
- Both played straight and lampshaded in an episode of The Cleveland Show:
Cleveland: C'mon, dad, he's probably not gonna scam us again!(Gilligan Cut to Cleveland, LeVar and Rallo all walking home, wearing nothing but bankruptcy barrels.)Cleveland: I can't believe he scammed us again!LeVar: (sighs) I don't even wanna think about how I'm gonna pay for this barrel rental.
- In the Viking episode of Histeria!, a bit featuring vikings raiding with the element of supprise. Afterward the raid targets comments "They took everything but the shirt of my back", prompting a second pass leaving said target in a bankruptcy barrel.
- Clarabelle Cow wears one in the Mickey Mouse short "Ye Olden Days", after Mickey and Minnie use all her clothes to make a Bedsheet Ladder.
- Private Snafu: In "Payday", Snafu winds up wearing nothing but a cardboard box after he loses all of his money playing craps.
- In one episode of The Fairly OddParents when Timmy, Cosmo, Wanda and Timmy's grandfather go into the world of black and white cartoons, Cosmo inadvertently causes The Great Depression and two investors appear wearing these.
- The Greatest Man in Siam by Walter Lantz. After the royal income tax collectors are done with the richest man in Siam, they give him a barrel to wear. Filmed in 1944, making it harsher in context.
- In the Mickey Mouse (2013) short "Good Sports", when Mickey explains the consequences of bad sportsmanship, the Goofy with bad sportsmanship is seen wearing a barrel that reads "loser" after the other Goofies beat him up for his bad sportsmanship.
- In The Sylvester and Tweety Mysteries episode "It's a Plaid, Plaid, Plaid, Plaid World", every Scot is shown wearing a barrel because of the plaid they use to make their kilts being stolen.
- In The Twisted Tales of Felix the Cat, Felix at one point accidentally pulls off a cow's hide in the episode "Mars Needs Felix", resulting in the cow's underwear being exposed. The cow promptly covers herself by putting on a barrel.
- The philosopher Diogenes embraced a life of virtuous poverty and lived in an urn. Probably as close as this trope has ever come to happening, even if Diogenes' urn was too large and heavy to be worn.
- Though not really broke, Barrel Man (real name Tim McKernan) used to wear nothing but an orange-painted barrel to every Denver Broncos home game for 30 years until his death in December 2009.
- As mentioned in the lead section, wearing a barrel was a common punishment for public drunkenness in medieval and early modern Germany and England. Since the rich tended to get sloshed in private, the poor were generally the ones arrested for public drunkenness.