Martha Stewart — 1960
Damn, Martha Stewart! We never realized you used to show. In any case, that is reality, as we can see here. The money manager and television character started out in diversion in a way we couldn’t have ever speculated. We are accustomed to seeing her in comfortable sweaters and pearls, baking and making things we would never be awesome. However, she really dealt with lobbies for Chanel, and utilized that cash to pay for school. Inconceivable!