| Description | Character | Guest Star | % Correct |
|---|---|---|---|
| Bart's Archnemisis | Sideshow Bob | Kelsey Grammer | 81%
|
| Helps Bart and Lisa rescue snakes on Whacking Day | Themselves | Barry White | 69%
|
| Play Moe's Tavern after the popularity of a new Flaming drink | Band | Aerosmith | 64%
|
| Homer's brother | Herb Powell | Danny DeVito | 64%
|
| Appears to Homer after he eats Wiggum's Chilli | Coyote | Johnny Cash | 61%
|
| Play Krusty's Comeback Special | Band | Red Hot Chili Peppers | 58%
|
| Play atop a wall dividing Springfield after a row about dialling codes | Band | The Who | 56%
|
| Homer's mother | Mona Simpson | Glenn Close | 50%
|
| Hires Homer to assist his remake of Mr Smith Goes to Washington | Himself | Mel Gibson | 50%
|
| Lisa's substiture teacher in an inaccurate cowboy costume | Mr. Bergstrom | Dustin Hoffman | 47%
|
| Mr Burns orders the Rolling Stones killed after seeing their performance | Band | Ramones | 47%
|
| Marge's high school boyfriend who doesn't want you to know about his busy hands | Artie Ziff | Jon Lovitz | 42%
|
| Catholic Priest who recruits Homer and Bart | Father Sean | Liam Neeson | 42%
|
| Chinese Civil Servant who suspects foul play in adoption | Madam Wu | Lucy Liu | 39%
|
| Homer's roofer friend who no one else believes exists | Ray Magini | Ray Romano | 39%
|
| Assist in Homer's campaign for Sanitation Commissioner | Band | U2 | 39%
|
| That man is the Real Seymour Skinner | Sgt. Seymour Skinner | Martin Sheen | 31%
|
| Defeated by Homer in election for Sanitation Commissioner | Ray Patterson | Steve Martin | 31%
|
| Crafty carney who was "beaten by the best" | Cooder | Jim Varney | 14%
|
| Stern Judge on the Springfield Circuit | Judge Constance Harm | Jane Kaczmarek | 8%
|