1. Sideshow Bob - The Simpsons, 'Cape Feare' (TV, 1993)
20th Century FoxIt's very hard to choose between the 16 episodes to date in which Grammer has voiced the brilliant Sideshow Bob. It's certainly true that the more recent appearances of the character have seen him relegated to comic relief, but when the show was in its prime, Robert Underdunk Terwilliger steadily grew into one of the most distinctive and complex supporting characters in The Simpsons universe. But for all the appeal of 'Black Widower', 'Day of the Jackanapes' or 'Brother From Another Series', 'Cape Feare' is still the best Sideshow Bob episode, and the best thing that Grammer has ever done. 'Cape Feare' begins with Bart receiving a series of death threats written in blood. These are being sent to him by Sideshow Bob, serving time in prison for attempting to murder Selma Bouvier in 'Black Widower'. Having pursuaded the parole board that he poses no threat to Bart, Bob is released and begins to stalk The Simpsons. The family are relocated under the Witness Protection Programme, but Bob is never far behind. As its title suggests, the episode riffs extensively on both versions of Cape Fear, particularly the 1991 remake starring Robert De Niro (the cinema scene, pictured above, is a direct reference). 'Cape Feare' has become a classic episode in its own right, with many of its ingredients becoming staples of future Bob episodes. But while he can't take full credit for the hilarious rake joke (created in post-production to fill out time), every other aspect of Bob's success as a character is down to Grammer. His delivery is witty and deliciously cruel, he brings credence to the character's more snobbish aspects, and he sings the entire score of H. M. S. Pinafore with great aplomb. It's a terrific all-round performance which turns what could be just another cartoony psychopath into a rounded, believable and thoroughly entertaining character.
Having heard Grammer soar on Gilbert and Sullivan, let's look at five performances in which he sank like a stone...