#4. Mayor McCheese (McDonald's Advertising)
Despite obvious ties to corporate money and a campaign plagued by rumors that he was threatening to unleash the Grimace on political opponents, Mayor McCheese was swept in by a landslide after former mayor Phineas Q. McRibbington stepped down to pursue a career of being delicious. Under his administration, Mayor McCheese resisted several attempts by McDonaldland's citizenry to eat his head, and even managed to reduce Hamburgling by 30 percent.
Rather than running on the issues, Mayor McCheese primarily campaigns against his frequent rival, the Burger King, whose autocratic regime saw a drastic increase in crime (most notably breaking and entering and possession of a Croissan'wich with intent to distribute), as well as the rise of the insidious "Chicken Fries," which stand as an affront to both God and Man. Also fondly remembered by Europeans for his moving speech to a divided Germany, where he famously announced "Ich bin ein Hamburger."
#3. TIE: The Mayor (Powerpuff Girls)
As the last of the monocle-sporting oligarchs, the Mayor-who dedicated his life so fiercely to politics that his own name has been superseded by his title-overcame the disabilities of being two feet tall and functionally retarded to secure a position of power in the City of Townsville. Since his election, crime has dropped to almost zero, with a corresponding rise in the success rate against giant monster attacks. According to his detractors, this is mostly due to the intervention of three super-powered little girls, but to be fair, the Mayor is the one who calls them on the phone.
Along with some devoutly pro-pickle policies, the Mayor seems to have run solely on the fact that he owns a sash with the word "mayor" written on it.
#3. TIE: Mayor Richard Wilkins III (Buffy the Vampire Slayer)
Probably owing to the fact that he was a hundred year-old demon in human form, Mayor Wilkins was able to reassure an entire city that absolutely nothing was wrong, despite an almost-weekly plague of attacks by the undead. Given that Sunnydale had two high schools and roughly eighty-six cemeteries, this may actually have more to do with the abject stupidity of the citizenry, but you've got to hand it to anyone who can put a positive spin on a yearly apocalypse. Also, he carried on a quasi-incestuous relationship with Eliza Dushku circa-Bring it On, back when that meant something.
It's not really a political statement per se, but before his term was cut short by a tragic/awesome explosion, Mayor Wilkins had announced plans to transform himself into a giant snake-monster. We're not really sure how that would help cut down on graffiti within the city, but we are pretty certain that it would look pretty kickass on the city seal.