1987
Kid Sister and Me
Bob and Susan Duff welcome Hilary to the family. Sister Haylie, who is two years older, inspires her sibling throughout childhood: "I always wanted to be like my older sister Haylie. When she learned to ride a bike, I had to as well. If she took ballet lessons, I did too. I took singing lessons because she did. It all just got more intense until it turned into careers for both of us," Duff tells the Calgary Sun
(The younger 1 is Hil )
1998
September 22
Ghost of a Chance
After appearing in a few TV commercials, Duff lands the lead role of Wendy in the feature-film comedy Casper Meets Wendy. The part marks Duff's first major role in a motion picture.
2000
Along Comes Lizzie
Duff auditions for Disney's comedy show Lizzie McGuire and is cast as the title character. The show eventually draws two million viewers per episode, becoming the network's highest-rated offering, making Duff a household name with the tween set.
2003
August 26
Topping the Charts
Duff releases Metamorphosis, which reaches No. 1 on the U.S. charts and goes platinum. The following year, she wins Nickelodeon's Kids' Choice Award for Favorite Female Singer as well as Best New Female Artist at the World Music Awards
2004
July
Dating Joel Madden
After being introduced by a mutual friend, Duff, 16, begins dating Joel Madden, 25, lead singer of the band Good Charlotte. "We were on the same level, even though he was so much older," Duff tells Teen People. She also stars in A Cinderella Story, which earns $50 million . For the soundtrack, Duff and Haylie record a cover of the Go-Go's' "Our Lips Are Sealed".
2005
August 16
Working With the Maddens
Duff's latest release, Most Wanted, is a compilation of her favorites from previous albums, remixes and some new songs. This time around, she cowrites and coproduces new material with boyfriend Madden and his brother Benji. It goes platinum and becomes her second No. 1 album
2007
Duff's Dignity
Duff debuts a more grown-up, dance-driven single "With Love," kicking off her latest release, Dignity, which peaks at No. 4 on Billoard's 200 albums chart. On the film front, the actress-singer plays a European pop star in the satire War, Inc. alongside John Cusack and Marisa Tomei.
Hilary Hooks Hockey Player
With heartbreak behind her, Duff moves on with new beau, N.Y. Islanders hockey player Mike Comrie. And Comrie seems like a catch: he gives Duff a Mercedes-Benz G-class SUV as an early 20th birthday gift in September.
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