The Simpsons: Every Sideshow Bob Episode Ranked Worst To Best

5. Sideshow Bob's Last Gleaming

Sideshow Bob Simpsons
Fox

In a slightly messy but still very funny episode, Sideshow Bob takes a break from attempted Bart murder and sets his sights on a bigger enemy: the TV industry. This is Bob at his most demented yet, espousing good old fashioned wholesome values while attempting to obliterate Springfield with a nuclear bomb.

After the first couple of instalments, Sideshow Bob episodes tended to get the epic treatment, and that’s certainly the case here. Bob’s plan is grandiose, and the military base in which most of the action takes place as a great setting. The episode also features guest star R Lee Ermey, of Full Metal Jacket fame, in his trademark role of a military guy who angrily shouts a lot.

The episode loses its sense of tension a little towards the end, but it’s no less funny for it, with Sideshow Bob’s fancy affectations a constant source of comedy throughout the episode. By this point he has transitioned to a full fledged supervillain, and spends much of the episode delivering self righteous monologues as only Kelsey Grammer can.

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Yorkshire-based writer of screenplays, essays, and fiction. Big fan of having a laugh. Read more of my stuff @ www.twotownsover.com (if you want!)