18. Todd Flanders
First appearance: “Simpsons Roasting on an Open Fire” (Season 1, Episode 1)
Notable appearance: “Dead Putting Society” (Season 2, Episode 6)
Voiced by: Nancy Cartwright
One of the great dynamics in The Simpsons is the fact that this heathen family lives directly next door to the Flanders family, Springfield’s resident Bible thumpers. And while the clash between Homer and Ned is a given highlight of the series, the relationship between their sons has provided us with just as many classic moments. And between the two Flanders kids, Todd outshines his older brother Rod.
Todd's so saccharine that you can’t help but want to simultaneously punch and box him up like a Christmas present. Some of great Simpsons moments include his participation in a mini-golf tournament against Bart, and when he got swept away by a raging river while playing baby Moses in Ned’s directorial debut. But unlike the other members of his family, Todd is very impressionable and often gets corrupted by the outside world. Even then, he’s still the most relentlessly naïve and innocent character that the town has to offer. Jokes ensue.