

The role that gained Stiles renown was Kat Stratford, opposite Heath Ledger, in Gil Junger's 10 Things I Hate About You (1999), an adaptation of The Taming of the Shrew set in a high school near Tacoma, Washington. She won an MTV Movie Award for "Breakthrough Female Performance" for the role, and the Chicago Film Critics voted her the most promising new actress of the year.