- Author's Saving Throw: Many viewers thought that Herbs Riches to Rags fate was too cruel an ending, so this episode was made to rectify that.
- Unintentionally Unsympathetic: We're expected to sympathize with Herb, who Homer supposedly owes a chance to rebuild his fortune. Unfortunately, "Oh Brother, Where Art Thou?" clearly indicated that Powell Motors was in serious trouble long before Homer came along, Herb repeatedly blew off his engineers' warnings that Homer's ideas were unworkable, Herb never did his job as CEO in supervising the project that would make or break his company, and Homer himself wasn't sure he would be able to do it, until Herb, rather than planning or going indepth with his half brother's ideas, instead badgered him into doing it. Homer only ever did anything Herb asked him to. As a result, Herb blaming Homer for Powell Motors' downfall makes him look like a self-centered asshole who refuses to accept responsibility for his own incompetence, and makes it questionable as to whether he even deserves a chance to rebuild his fortune. Possibly admitted in a later gag, where it's suggested Herb has made a habit out of losing and regaining his fortune, seemingly without Homer's involvement. Those who still hated him because of this and that heard years later that Herb became broke again, this time without anything involving Homer, saw this as Laser-Guided Karma for his unsympathetic act.
YMMV / The Simpsons S 3 E 24 Brother Can You Spare Two Dimes