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“Brother, Can You Spare Two Dimes?” is the 24th episode of The Simpsons’ third season. It was originally supposed to be the opener for season four, but FOX decided to air it earlier to promote the series premiere of Martin; thus, it became the finale of season three.

Plot
Homer J. Simpson “wins” the First Annual Montgomery Burns Award for Outstanding Achievement in the Field of Excellence, a fictional $2000 prize awarded by Montgomery Burns. The name of the “award” was hastily concocted by Burns on the spot in an attempt to convince Homer to sign a waiver freeing the nuclear plant of all liability for Homer’s recently discovered sterility. Joe Frazier is the host of the award ceremony, which features extraordinary extravagance (including a lengthy opening) but only the one $2000 prize awarded to Homer. Despite planning on using the money for the Spinemelter 2000 vibrating chair, Homer agrees to loan the money to his bitter half-brother Herb Powell who, ruined by Homer previously, is now a hobo. Herb’s idea to become rich again is by making a machine to translate a baby’s words into actual English. Using Homer’s money to develop his invention, which is an instant money-making success, Herb becomes rich once again. Along with returning the money to Homer, he buys several gifts for the Simpson family, including a washer-dryer for Marge, an honorary membership to the NRA for Bart and a subscription to the Greater Books of the Western Civilization for Lisa. Herb then tells Homer that his gift to him is that he forgives him for ruining him in the first place, and he and Homer re-establish a brotherly relationship. Finally, Homer is rewarded for his generosity and faith when Herb has a truck pull in with Homer’s vibrating chair.

Cultural references

1. The episode title is a play on the Great Depression-era tune “Brother, Can You Spare A Dime?”. (Mr. Burns sang this song in the second season episode “Two Cars in Every Garage and Three Eyes on Every Fish”). Additionally, “two dimes” is gambling slang for two thousand dollars, which is the amount Homer lends Herb.
2. One of the men that sits with Herb by the fireplace in the beginning of the episode looks very similar to Charlie Chaplin’s character The Tramp. The Tramp also eats a boot in the Chaplin movie The Gold Rush.
3. The images Homer sees when sitting in the Spinemelter chair parodies 2001: A Space Odyssey.
4. Homer reminisces about sitting on the couch while watching Dallas (specifically Kristin’s revelation that she shot J.R. Ewing), the Hands Across America charity event, and the Berlin Wall coming down, which he switches over to Gomer Pyle, U.S.M.C..
5. Homer’s line “excuse me while I kiss the sky” originates from the Jimi Hendrix song “Purple Haze”.