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. He also gets attacked regularly by various animals for no reason throughout the series.
Trudy Proud - Trudy is Oscar's wife. While they do love each other deeply, they have had their obstacles. Oscar often get fed up with Trudy's bossy behavior towards him and Trudy does get fed up with his childish demeanor. Oscar tends to flirt with attractive women he barely knows but he never intended on actually cheating on his wife. Despite their obstacles, they are caring parents who do love each other and work together to raise their kids well.
Penny Proud - Penny is Oscar's oldest daughter. Being a teenager, Penny does have her moments of rebelling against her father but there is no doubt the two of them are really close. Oscar refers to Penny as "Baby Girl" and is extremely overprotective of her. Penny is very loving towards Oscar but does get irritated when he says she can't date boys.
Suga Mama - Oscar's mother. They do have a complicated relationship but at the end of the day, they are still family. There have been episodes that prove the two really do love each other and look out for their well-being but most of the time, they are often seen insulting each other or Suga Mama being outright abusive towards him. It's revealed in "Penny Potter" that Suga treated Oscar the way she did because she was treated the same way growing up, although she never really noticed it before.
Bobby Proud - Oscar's older brother. Oscar has always been in his brothers shadow. He was often ignored by his family while Bobby got all the love and affection that a child needs growing up. Despite this, Bobby and Oscar themselves appear to be pretty close. Bobby often helps Oscar out with his business (like providing the music when he was going to pitch his latest snack creation).
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. He does love Trudy dearly but tends to do this as Trudy's bossy attitudes tends to make him rather irritated. This habit is unusual for a children's show, this implies that he attempts to commit adultery, even though he never would come around to actually doing it.