10 Times The Simpsons Got Political
2. Sideshow Bob Roberts
Sideshow Bob Roberts might be more of a Sideshow Bob episode than a political episode, but it still deserves credit, and not just for the much needed lampooning of Rush Limbaugh.
Featuring ex-con Bob running for Mayor of Springfield with the support of radio host Birch Barlow - and stuffing the ballot box with the name of deceased residents, and their pets - this Season 6 outing manages to be one of the better political outings and one of the better Bob appearances.
Spoofing the Watergate scandal, the Republican party, Limbaugh, and the Democrats as well, it's as close to a perfect political episode as you'll come, with perhaps one exception. Best of all, however, is that while knowledge of politics helps the episode, it's not necessary to enjoy it, making it something of a timeless classic.