Clubba Hubba - S1-E3
Revealing mistake: During his first conversation with Dr. No, Will Smith mouths "strings of Arabians" as Richard Roundtree says it (it can't be a line he rehearsed with Carlton, because his character has no clue about that branch of conversation). (00:11:00)
Clubba Hubba - S1-E3
Continuity mistake: As Carlton and Will battle out with their "I bet he won't", "I bet he will", Will is holding his drink with his left hand. When he breaks the fourth wall with a joke in a new shot, the glass switches hands. (00:05:00)
Answer: He believed he was asserting his independence and individuality, not giving in to the conformist rich society. Movie quote, "I don't act this way to change the world. I act this way, so the godamn world doesn't change me."