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 him and calls him "brother" again.
- 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.