Current age: 27
Career at 20: Hilary turned 20 six months after the release of Dignity, her fourth album, which featured a worldwide tour by the same name and the single "With Love." She also played a pop star in the May 2008 movie War, Inc. alongside John Cusack.
Relationship status at 20: Hilary was first linked to her now-husband, former NHL player Mike Comrie, in Summer 2007.
Quoted at 20: Hilary told Cosmopolitan in January 2008 that she was starting to feel more like an adult, saying, "This has been a big cleansing year for me. I learned a ton about myself, and I became really independent. I feel like I grew up a lot."