#10 Jenny Shimizu
American model and actress, Jenny Shimizu was working as a mechanic before starting a career in modeling. She was approached by a Calvin Klein representative to do an ad for a flagrance, and that’s how her career took off. Jenny had quite an interesting life. She dated Angelina Jolie and declared she had some sexual encounters with Madonna too. Actually, Jolie said that she fell in love with Jenny the moment she saw her. The model’s Asian features and masculine physique made her special particularly for fashion designers constantly hunting for that one of a kind model.