Funky Winkerbean
The Funky gang consists of a large ensemble cast whose members play out their roles on two main stages. The first is Westview High School, where the current generation of students, including Wally, Becky and Monroe, interact with principal Fred Fairgood, band director Harry L. Dinkle, Cliff the security guard, and Les Moore, a former student who now teaches English at the school.

Les lives with his wife, Lisa, above Montoni's Pizza, where Funky has worked since he graduated from Westview High and which he now co-owns. There they share the stage with Tony Montoni, Cindy Summers and Crazy Harry.

These two generations of characters allow Funky Winkerbean to touch on the issues that resonate with today's young adults while also following the original post-graduate Funky gang as they make their way in the real world.

Wally
Funky's cousin, who was voted "Most Likely to Achieve Mediocrity" in high school.

Becky
Becky and Funky's cousin, Wally, were dating in high school. She lost her arm when they were in a car accident. She now works as a waitress at Montoni's.

Monroe
Monroe was one of the most ambitious students at Westview High School. In the yearbook, Monroe was voted "Most Likely to Succeed...at Burning Out Before Graduation."

Fred Fairgood
He is the principal of Westview High School. He is married to Ann and is Darin's father.

Director Harry L. Dinkle
Harry is not only the world's greatest band director, but the world's greatest fund-raiser as well.

Cliff
Cliff is the security guard at Westview High School.