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Lavigne worked further with The Matrix and also with singer-songwriter Cliff Magness.

In December 1999, Lavigne was discovered by her first professional manager, Cliff Fabri, while singing country covers at a Chapters bookstore in Kingston, Ontario.Ken Krongard, an A&R representative, invited Antonio "L.He invited her to contribute vocals on his song, "Touch the Sky", for his 1999 album, Quinte Spirit.She later sang on "Temple of Life" and "Two Rivers" for his follow-up album, My Window to You, in 2000.That same year, she made her on-screen feature film debut in Fast Food Nation.

In 2008, Lavigne introduced her clothing line, Abbey Dawn, and in 2009 she released her first perfume, Black Star, which was followed by Forbidden Rose in 2010, and Wild Rose in 2011. Whibley and Lavigne continued to work together, with Whibley producing her fourth album, as well as Lavigne's single "Alice", written for Tim Burton's film Alice in Wonderland.In July 2006, Lavigne married her boyfriend of two years, Deryck Whibley, lead singer and guitarist for Sum 41. In school, she was sometimes kicked out of class for misbehaving. Her father bought her a microphone, a drum kit, a keyboard, and several guitars, and converted their basement into a studio; following his own love for music Jean-Claude led the family to church at Third Day Worship Center in Kingston, Ontario, where he often played bass.When Lavigne was 14 years old, her parents took her to karaoke sessions.Lavigne took a break from recording music, pursuing careers in feature film acting and designing clothes and perfumes.She voiced Heather, a Virginia opossum, in the animated film Over the Hedge in 2006.Sarubin told Hit Quarters that they initially struggled; although early collaborations with songwriter-producers including Sabelle Breer, Curt Frasca and Peter Zizzo resulted in some good songs, they did not match her or her voice.