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To show that a character is in such dire financial straits that he's literally "lost his shirt", the otherwise naked character will resort to wearing a large barrel held up with suspenders. Primarily seen in cartoons. This image probably came from a punishment for public drunkenness in Germany and England, where drunks had to wear a booze barrel (a "drunkard's cloak" or a "new-fashioned cloak"). It's unclear how barrel wearing became associated with bankruptcy (perhaps from the assumption that public drunkards are always hard up for money?), but the trope stuck.
Examples:
  • 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.
  • Spoofed in an old Goofy cartoon: After playing poker, Goofy is seen (apparently) wearing a barrel, holding it up with both hands. He then hails a taxicab and, in a brilliant subversion, empties the barrel (which was filled with money) into it.
  • In Kevin And Kell, when Kell's mother Elanor loses her life savings day-trading, she suddenly goes from wearing a coat composed of live minks to a barrel.
  • Although no one wears it, there is the barrel in the neighbourhood of El Chavo Del Ocho where the titular Chavo (the poorest person in the neighbourhood) seems to live in.
  • In Sierra's Jones In The Fast Lane, failing to buy new clothes for your character every once in a while will eventually cause the character to resort to wearing a barrel.
  • In the episode of Futurama, "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.
  • Appeared in one short Dilbert arc. "Our new dress-code is barrels."
  • 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?"
  • 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.
  • The Comics Curmudgeon references the trope and its usage in this installment of 'Six Chix.