"Sideshow Bob Roberts", written by Bill Oakley and Josh Weinstein, is my favourite Sideshow Bob episode. Whilst many will point to "Cape Feare" as Sideshow Bob's defining moment, "Roberts" manages to be funnier than its predecessors and contemporaries, containing biting yet light-hearted political satire and typical Simpsons humour, and also have a unique plot that is not as simple as "Sideshow Bob tries to kill Bart". This essential element of differentiation that newer Bob episodes lack is what makes "Roberts" and other classic Bob episodes, for example, "Brother From Another Series" so fulfilling to watch.
"Attempted murder? Now honestly, what is that? Do they give a Nobel prize for attempted chemistry? Do they?"
Humour-wise, "Roberts" never fails, succeeding in being one of the few episodes where I think every joke hits. Whether it's Barts line about having 2 mortal enemies, or the fabulous sequence including Lionel Hutz, "Roberts" continually has me in stitches even on immediate repeat viewings. "Roberts" is the quintessential example of the Simpsons in their comedic prime. Jokes are well timed and all within character. Yet the beauty of the episode is, that even with these numerous jokes, the episode hardly loses footing and stays on track, more than can be said for more recent episodes. "Roberts" weaves jokes so delicately and masterfully into its plot that without realising, you can be laughing away whilst the plot chugs along. This too highlights the mastery of the comedy in "Roberts", it waits for no one, it executes it perfectly, and leaves the audience to do the rest. There's no over explanation or unnecessary build up - it fires out the gags rapidly, but not so much as to overflow the episode.
It's important to note though, that although satirical, "Roberts" is hardly a politically themed piece of television. Rather, it relishes in jabbing fun at both ends of the US political spectrum, remaining neutral (okay, slightly left-wing) and light-hearted, yet simultaneously acerbically witty, whether it be referring to Republicans as outdated, and stupid (applauding a water dispenser as their mayoral candidate) or Democrats as illiterate and sleazy. This not only enhances the comedy in "Roberts" but also makes it multi-dimensional and appealing to all audiences - the beauty of the classic era.
Animation-wise the episode is vibrant and exciting, if not spectacular. Unlike some episodes, "Roberts"' story takes us to many places in Springfield. The library, the Simpson home, the nuclear power-plant, the town hall, the school, and even the graveyard. Whilst not as essential as comedy in terms of enjoyment, there is no doubt good direction and varying environments help make an episode more captivating. Animation wise, my favourite moments here have to be:

Bart's stance here is just great, perfectly conveying his shock and leading on brilliantly to his "mortal enemies" line.

With the shading and atmosphere, Bob's speech (ie.long laugh) did excellently in reminding us of Bob's presence and wickedness.

Smithers' scene also helped at some drama and conflict to the episode.

This nice reference to
All The President's Men is certainly an interesting (I hate my limited vocabulary) angle and helped what would be a perhaps boring scene (Lisa at the library) become that little bit more enticing.
All this culminated results in one fine episode of the Simpsons, that succeeds in giving us an interesting and unique plot, plenty of laughs, and excellent satire. Whilst one could say that episode lacks an emotional core, and the lack of direct Bob-Bart interaction could be.. an anti-climax, the episode, without a doubt, succeeds and fulfils what it set out to be, and very well at that.
A+
10/10