6. Cape Feare
Season Five
1993
Sideshow Bob had plenty of appearances fighting Bart and his cohort Lisa. He even teamed with his brother Cecil, in a hilarious guest spot from David Hyde Pierce. But the best and pure quintessential battle that defined the immortal feud between Sideshow Bob and Bart begins and ends with “Cape Feare.”
Yet another excellent spoof of an fantastic movie by the creative minds on the show, Sideshow Bob breaks out of prison and hunts down Bart, taunting him and harassing him a la Max Cady. This involves writing him letters written in his own blood (eventually leading to Bob collapsing from blood loss), driving around in a truck announcing who he will not kill (Bart was excluded from the list of course), laughing loudly during a movie cigar in hand (much to the chagrin of Marge and Homer who has a bigger cigar), and Homer hiring a wimpy vigilante who begs Bob to leave town. After every measure fails to chase Sideshow Bob off, they eventually flee, and go through witness protection, to live their lives as… The Thompsons.
In possibly the most memorable moment of the episode, two FBI agents are trying to get Homer to play along and respond to his new name Mr. Thompson, and Homer can’t quite comprehend what the point of the practice is. And of course, there’s their new residence on a house boat in Terror Lake, to where Bob and Bart eventually square off. Bart, in his infinite ingenuity, convinces Bob to sing the entire HMS Pinafore for him. But my two favorite moments involve the spoof of “I Love Lucy” where the family sings “Three Little Maids” with Bob being tortured underneath their car, and Bob’s confrontation with an endless sequence of rakes to the face. “Cape Feare” is filled with numerous hysterical moments and is definitely the best confrontation between the ex-clown and his nemesis.