Sideshow Bob (The Simpsons)
While he hasn’t been a driving force behind entire seasons of The Simpsons, Sideshow Bob has been giving Bart Simpson and other characters trouble for 25 years now, which automatically makes him one of the best villains of any given year. Voiced with perfection by Kelsey Grammer, Sideshow Bob (real name Robert Underdunk Terwilliger) has had a decades-long plot to destroy the life of Bart Simpson, and occasionally former employer Krusty the Clown, and pretty much anyone else who tries to corrupt his schemes.