In The Movie, when Penny (the clone) climbs on the mountains and punches a boulder.
The only time Oscar finally comes out on top was when Penny had a chance to win a Million Dollars and had to shoot a ball from Midcourt at a basketball game owned by The Wizard. His past is brought up when he accidentlly cost the team the game as a teenager and has been ridiclued ever since then. Despite it, Penny selects him and he's there at the court in two seconds and the entire crowd (Even his mother) cheers him on. He shoots... And hits it going in perfectly in the net.
When LPDZ wins the Hip Hop Helicopter Dance Competition.
In the episode "Enter the Bullies" Oscar got into a fight with Mr. Gross, the Gross Sisters' father, which ended rather badly for him. At the end of the episode, after Penny has brokered a truce between herself and the Sisters, Oscar once more visits Mr. Gross and says that even though they both got off on the wrong foot, they have to set a proper example for their children. Gross himself agrees, saying they "gotta do it for the kids", and they both part on amicable terms. Take thatBroken Aesop Episode..
In a Valentine's Day episode, Penny discovers that a boy in a wheelchair has got a crush on her and, not wanting to make him feel bad because of his disability, becomes his girlfriend. Only it turns out the kid is a manipulative Jerkass who leaches off Penny's family while being completely disrespectful and eventually Penny works up the nerve to tell him off after he ruins her family's vacation at a ski resort, slamming the door in his face. Penny asks Oscar and Trudy not to get mad at her for what she did, but they're both very proud for how she stood up for herself and for the family.
Trudy gets one in the episode when Penny lies to her parents about going to the night club. When she finds out, she gets very angry and demands that Oscar lets her drive the car!
In "The Forbidden Date," Carlos gets one when he saves Bebe and Cece when they end up on a roller coaster.