SPRINGTIME FOR SPRINGFIELD
Homer is audited by the IRS, where his auditor realizes that because Homer's tax forms are completely incomprehensible, nobody has ever checked them.
His auditor confides in Homer the idea that a failed business makes more money than a successful one, inspiring Homer to use a play for his failed business. He is able to convince Kirk Van Houten to help him in his scheme.
The two find a truly horrible script in "O Springfield, My Springfield!", a truly horrendous "love-letter" to the town written by Comic Book Guy, containing glowing numbers about Springfield's worst people and biggest blunders.
After tricking the people of the Retirement Castle (including Grampa) into over-investing, they get a director in Sideshow Bob, who is currently on parole.
Despite everyone in Springfield initially finding it horrible, a group of trendy art critics from Capital City manage to change their minds, calling it an ironic, postmodern masterpiece.
At the courtroom, Homer gives a heartfelt closing statement about how he actually brought people together with his scam, leading to Judge Snyder sentencing the two to 5 years of community service, specifically producing, directing and starring in a yearly musical revue for the Springfield Community Playhouse, where all ticket proceeds will go towards fully refunding every investor with interest.
By the end of the sentence, Homer and Kirk have become theater impresarios, the Retirement Castle is upgraded, and Sideshow Bob has befriended the two to the point he almost doesn't feel like killing Bart. (Almost).