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
* {{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 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.
* 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 ''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.