This was actually the last episode I chose, and it came down to a multitude of episodes for the fifteenth slot. This one won out mainly because I enjoyed Homer's brief and unsuccessful stint as a responsible parent. Springfield legalizes gambling, Mr. Burns builds a casino and Marge gives up everything to become a slot jockey as the expense of being taken... by Gamblor.
So here's the episode from season nine I was talking about. I think the main reason I selected it is the Homer and Mojo subplot where Homer gets a helper monkey. Not because he is handicapped, mind you, but because he's lazy. Homer of course corrupts Mojo when he has him steal donuts and later teaches him to fester on the couch in his own filth. The main plot of Bart and Lisa dueling for ratings on Kids News is also pretty funny, but Mojo will always be remembered.
This episode is included for no other reason than the brilliant and hilarious musical version of A Streetcar Named Desire, directed by Jon Lovitz. The basic story is Marge is going to be in a town production of Streetcar and Homer is, well he's Homer. You can view the play here but I am going to present you with something completely different, but entirely awesome. Maggie is put in 'Ayn Rand School for Tots' where pacifiers are not allowed. In spectacular Great Escape parody form:
Normally you wouldn't think an episode with twenty-two separate stories would end up being coherent at all, but this episode manages that and is funny to boot. From 'Skinner and the Superintendent' where Skinner convinces Chalmers that Krusty Burgers are 'steamed hams' (and that Aurora Borealis is occurring in his kitchen), to Apu's five minutes of party-time, to Nelson finally getting his, to the interwoven Pulp Fiction parody (which I think is my main reason for liking this episode) involving Chief Wiggum and Snake.
Classic episode. Mr. Burns makes a bet that his company softball team will beat the Shelbyville softball team for $1 million (which he intends to 'throw on the pile'). So in order to ensure this he hires various MLB superstars. However, tragedy befalls each one except for Homer's replacement, Daryl Strawberry. Homer's talent is not wasted, however: