This episode's plot didn't make any sense - Grimes somehow has a son who is trying to kill Homer, and who decides to do so by rigging a Mardi Gras election so that Homer wins and rides on a float that doesn't have working brakes so he rolls down a hill and doesn't get off and dies by hitting a swordfish museum. Eh? This episode fails completely as a "murder mystery", because rather than being a made up of a coherent set of clues and red herrings that eventually connect in a logical manner after the characters search for the truth, its just a bunch of stuff that happens/gags, with "clues" abruptly and awkwardly popping up when the writers realise they need to advance the plot. This episode really doesn't make use of Bob at all. The idea of him helping the Simpsons is interesting, but I'm not even sure John Frink and Don Payne know who Bob is. He has these flat, sterile lines - mostly used to deliver dry exposition - that have not an ounce of the poetic eloquence and verbosity that makes Sideshow Bob such a special character. Grammer does a good job with what he has, but he has very little to work with. As well as these fatal flaws, the episode has very little in terms of actual comedy. You have these strange and outlandish attempts at slapstick, with Maggie being sucked up by a hoover, Bob being repeatedly (and rather tediously) electrocuted, as well as a dragged out montage of Moe's pickled egg jar and some cheap gross-out jokes involving (sigh) Homer's grossly shrivelled body, Rainier Wolfcastle's penis, some guy's exposed skull... The more I think about this episode, the more I am disappointed in how lazy, cheap and generally lame it is.
Somehow, despite this this glut of bizarro wackiness, the show has some time to spare - which it fills with a pointless and incredibly boring scene that manages the incredible feat of making less sense than the rest of the episode! Bob - a convicted felon: one who was let out on the promise of finding a man attempting kill Homer (a stupid and nonsensical premise itself), who we have been explicitly told is going back to prison after he accomplishes this, who has been shot with rhino tranquillisers and is being taken back to prison by the police as the episode ends - somehow ends up in Bart's bedroom, attempting to kill him. He then magically realises he cannot do this because he's grown attached to Bart, in a moment that is neither funny nor touching nor used to advance the plot of the episode. It exists only to allow a song to take place! Now, I like that that's a convention of Bob episodes, but were they really so lazy that they couldn't find a way to fit a song somewhere into the actual episode in a way that actually fits in with what's happening? Because the answer to that question is "yes, yes they were", the song really has nothing to go on and is thus completely meaningless and ineffectual. This could be excused if it were funny or interesting somehow, but it isn't. Its shockingly bland and makes the already erratic and disjointed nature of the episode even more jarring. When they needed to fill some time in "Cape Feare", another Bob episode, they did so with one of television's greatest, funniest and most iconic pieces of slapstick ever - the rake gag. They may as well have filled the spare time in this one with three minutes of a blank screen. It would've been just as boring, but less confusing and inoffensive.
This episode is just so weak. Everything about it reeks of a show that has run out of ideas for what to do with one of its finest recurring characters, from the stupid and lazy premise of "Frank Grimes's son wants to kill Homer" which is nonsensically wacky and defies the entire meaning of the great episode that Grimes is from, to the silly gags that substitute for plot elements and filler. The best thing I can say about this episode is that, at the start at least, they sort-of tried to give it an plot, that it has one or two decent gags amongst the wreckage, and that Kelsey Grammer makes things a bit different than usual. If only stuff like, you know, the story, the writing, the humour, the mystery, and the characterisations were better, then it might actually be a decent episode. 3/10