Episode - 8F23
First Aired - 8/27/1992
In this sequel to "Oh Brother, Where Art Thou," Herbert Powell, Homer's once-wealthy half-brother, is now homeless and searching for the next new idea to take him back to the top — and all he needs is Homer's $2,000 prize money he got at a (rigged) award show and a place to stay (the Simpsons' house).
This episode contains examples of:
- As Himself: Joe Frazier
- Attention Deficit... Ooh, Shiny!: Homer is impressed with the drinking bird.
- Bookworm: Lisa really wishes to get a subscription for the greatest books of Western canon. Herb obliges.
- Boring, but Practical: Marge's idea of what to do with the money that Homer won.
- "Good Luck" Gesture: Homer crosses his fingers on both hands when he's expected to receive the First Annual Montgomery Burns Award for Outstanding Achievement in the Field of Excellence.
Homer: (crossing fingers) Please, please, please, please, please!
Lisa: Dad, you know you won!
Homer: Don't jinx it!
- Jerk with a Heart of Gold: Herb. He treats Homer pretty badly (due to still not forgiving him) and only hunts him down to use his money, but he is a good uncle and gives every family member their own gift on top of paying the money back. And Herb eventually does forgive Homer, calls him "brother" again, and bought him the massage chair he wanted.
- Rags to Riches: Herb
- Random Events Plot: The commentary notes halfway through "As you can see, we still haven't figured out the plot of this episode. We just wanted to bring Danny back."
- Self-Made Man: Herb became one again.
- Sequel Episode: To "Oh Brother, Where Art Thou".
- Homer's fantasy while on the massage chair is reminiscent of the 'star gate' sequence in 2001: A Space Odyssey.
- Special Guest: Danny DeVito as Herb Powell
- Take That: Done by Bart and Lisa during Homer's award ceremony. Note that the show had lost at the Emmys the previous year.
Lisa: This show is the biggest farce I ever saw.
Bart: What about the Emmys?
Lisa: I stand corrected.
- Theme Tune Cameo: The show's theme plays when Homer wins the award.
- Turn Your Head and Cough: Part of Homer's description of his physical:
Marge: How was your day at work, dear?
Homer: Oh, the usual. Stand in front of this, open that, pull down this, bend over, spread apart that, turn your head that way, cough.