Julia Stiles – 39

The ‘90s was an era that saw chick flicks invade the big screen. One of the most memorable films of the genre is 1999’s 10 Things I Hate About You, with Julia Stiles playing the leading lady Kat Stratford opposite Heath Ledger. Her performance earned her an MTV Movie Award and propelled her to prominence. Some of her distinguished acting credits come from movies like Save the Last Dance, The Bourne Identity, and Silver Linings Playbook. Her most recent project was the 2019 crime film Hustlers. 

Stiles also ventured into television and was notably featured in the series Dexter. She received numerous nominations for her work. Despite her celebrity status, Stiles chose to pursue her college degree and graduated in 2005 from Columbia University. The former teen-star married Preston Cook in 2017. The couple welcomed their first son, Strummer Newcomb, in October of 2017.