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:
* AsHimself: Joe Frazier
* AttentionDeficitOohShiny: Homer is impressed with the drinking bird.
* BeyondTheImpossible: Homer somehow has over 100% body fat.
* {{Bookworm}}: Lisa really wishes to get a subscription for the greatest books of Western canon. [[GeniusBookClub Herb obliges]].
* BoringButPractical: Marge's idea of what to do with the money that Homer won.
* GoodLuckGesture: 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!
* JerkWithAHeartOfGold: 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.
* RagsToRiches: Herb
* RandomEventsPlot: 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."
* SelfMadeMan: Herb became one again.
* SequelEpisode: To "Oh Brother, Where Art Thou".
* ShoutOut
** Homer's fantasy while on the massage chair is reminiscent of the 'star gate' sequence in ''Film/TwoThousandOneASpaceOdyssey''.
* SpecialGuest: Danny [=DeVito=] as Herb Powell
* TakeThat: 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.
* ThemeTuneCameo: The show's theme plays when Homer wins the award.
* TurnYourHeadAndCough: 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.