Sorry I'm a little late on this, but I had been busy.
Sweet Seymour Skinner's Baadasssss Song is an understated season 5 episode that effortlessly merges strong character depth and a great sense of humour, not that that's anything new in the classic era.
Skinner has always been one of my favourite secondary characters. After a number of great supporting roles as well as playing a love interest to Patty in Principal Charming, this episode in particular expands on what we know of this man.
The episode begins with a very memorable setpiece indeed. SLH being brought for show and tell followed by the chaos in the airvent delivers a great start to the episode, whether it's the class in awe of the dog or one of Groundskeeper Willie's finest hours. The problems ultimately leading to Skinner's firing (with Chalmers in great form, no doubt) is a nice way to close things out and make what happened up to this point resolve with the proper payoff.
From this point, I really enjoy how you've basically got the two stories going on that are very much related to each other. There's Bart developing a friendship with Skinner, as the two interact informally in a way never thought possible. Interestingly, Skinner and Bart work just as well as friends as they do enemies, though we know it would have to go back to the status quo by the end.
Meanwhile, we get a great look at Flanders in the principal's chair. It's a prudent choice that such an amicable character is used here as opposed to some maniacal tyrant. Ultimately Ned's easy-going demeanour has the school not in harmony but in shambles. However, I absolutely loved that the conclusion to this story by Chalmers is determined not by the state of the school but the prayer. It gave way to one of my favourite lines...
"That sounds like a prayer. A prayer...in a public school system? God has no place within these walls, just as facts have no place within organized religion."
So what else does this episode comedically? I always struggle in these classics to name moments because it's nearly end to end that less stands out above the rest. However, I've always been partial to the Billy and Cloneasaurus as well as the hilarious double standard the students take at the assembly with Flanders and Chalmers.
A bonafide classic and one of my favourite episodes of the fifth season. Oakley and Weinstein deliver and provide a incredible balance of character and humour that foreshadows their showrunning style just a little over a season later. 5/5 (A)