Oakland in Blue is a short about two friends; Kennedy, a recent college graduate, and local rap artist, Marcus. Their struggle to launch a successful independent record label without compromising their integrity is conflicted by the temptation of, 'Legit versus Street,' threatening their lifelong friendship. The story begins as Kennedy is busy getting prepared for their first record release party and performance. Issues arise when Kennedy's uncle, Big Ish, a streetwise boss and local businessperson, insists the $10,000 Marcus borrowed is returned to Ish that night. When Kennedy learns of the situation, he is forced back into his delinquent past in attempt to save his future.