He is the owner of a factory named Proud Snacks (which makes anybody who eats them sick, except Peabo, who is the only person who likes them). Penny shows early signs of this as well and Suga Mama repeatedly makes references to Penny "taking after her daddy."
He loves his family very much but has a strong weakness for beautiful women. He often flirts with other women and almost cheats on his wife Trudy with Wizard Kelly's gorgeous wife. Oscar also has problems with Trudy ruining his fun and perfect moments. In spite of his rivalry with Wizard Kelly, he does enjoy coming and going to his stores and restaurant for his amusement.
Oscar Proud was born on May 18, 1966, to his father Percy Proud, and his mother Suga Mama, during his childhood, his parents often favored his older brother Bobby Proud, over him, which made Oscar very jealous of him.
Oscar is best friends with Felix and the two often get wrapped in get-rich-quick schemes together. They also have a lot of things in common, including sports, watching TV, and flirting with attractive women, which usually ends them in trouble with their wives.
Some running gags throughout the series include Oscar getting into trouble, causing trouble, people complaining about his nasty snacks, yelling Trudy's name whenever seeing ridiculous, and getting into arguments.
Oscar Proud bears a striking resemblance to his late father, Percy Proud.
Penny, Trudy, Oscar, Suga Mama, and Dijonay are the only characters to be in all the episodes.
Despite being a married man, Oscar frequently hits on women other than his wife. Unusual for a children's show, this implies that he attempts to commit adultery, even though he comes to his senses before he can consider it.