50. Hilary Duff With Her Sister Haylie

Hillary first broke into show business in the 1990s. She starred in an uncredited role in the series True Women from Hallmark Entertainment in 1997. The following year, she made it to the starring part of Casper Meets Wendy, she was able to book more acting projects after. Haylie, on the other hand, studied ballet and started performing with the Houston Metropolitan Dance Company. Her skills led her to land multiple acting gigs such as The Amanda Show, Napoleon Dynamite, and Love Finds a Home.

With their movie Material Girls’ promotion, Hillary mentioned in an interview with People that she learned a lot from her sister, and there has never been a sibling rivalry. Hailey even guessed her sister’s crush in just one try. If you’re curious who he is, it’s The Notebook’s leading man Ryan Gosling. Fun fact, as they both have families, the two chose to be neighbors.