4. LaToya Jackson in Playboy: She was considered the prettiest of the Jackson sisters back in the day. But she was also called the “black sheep” of the family for being talent deficient. She is the only Jackson sibling who failed to produce a record that went gold or better. Her shocking Playboy spread was her personal coming out party but it humiliated the Jackson clan. She was Kim Kardashian before Kim Kardashian. With no discernible skills, she used her face, famous name and body to attain national notoriety.