Lavigne teaches herself to play the guitar and begins to showcase her powerful voice at local festivals, country fairs and even a Canadian Tire celebration. Her first manager, Cliff Fabri, discovers her two years later at age 14 singing in a bookstore.
L.A. Reid, head of Arista Records, signs Lavigne to a $1.25 million contract when she is 16. She drops out of high school and moves to New York to record her first album. Arista provides her with country music to record, but after six months of working with cowriters, it becomes obvious that the singer is more interested in rock. The young singer-songwriter soon ditches the setup and moves to L.A.
Dressed in skater pants, Lavigne appears on the cover of her debut album, Let Go, which sells more than 13 million copies worldwide. Thanks to the singles "Complicated" and "Sk8er Boi," the album becomes the third biggest-selling album of 2002, and Lavigne earns five Grammy nods.
Lavigne takes a more serious approach with the release of her second album, Under My Skin. It debuts at No. 1 on the Billboard 200, and goes on to sell 2.9 million copies. "I was involved in every aspect of making this record. I'm very hands-on," Lavigne says on her Web site. "I understand the whole process so much better this time because I've been through it. I'm really picky with my sound."
Lavigne, 19, shows up on vacation in Rome, Italy, with her new boyfriend, fellow Canadian (and former Paris Hilton beau) Deryck Whibley, 24, lead singer for the punk-pop band Sum 41. A year later, on June 25, after winding down her European tour, Lavigne gets engaged to Whibley in another romantic part of Italy – Venice.
Lavigne's skater image softens with a fashion spread for Harper's Bazaar and PEOPLE's 50 Most Beautiful People issue. "When you go from 17 to 21, you change a lot. Every girl does. I'm just growing up," Lavigne tells PEOPLE. In May, the animated comedy Over the Hedge and Fast Food Nation screen at the Cannes Film Festival. Lavigne provides the voice of an opossum in Hedge and makes her feature debut in Nation.
Lavigne, 21, marries Whibley, 26, in a nondenominational outdoor ceremony at a private estate in Montecito, Calif. The singer wears a custom-made ivory strapless Vera Wang gown and a long veil. The couple's first dance is to the Goo Goo Dolls song "Iris."
Lavigne debuts her tongue-in-cheek single "Girlfriend," kicking off her upcoming third album, The Best Damn Thing. In April, her single and her album reach No. 1 on the Billboard charts. By July, Lavigne is sued by members of The Rubinoos, who claim "Girlfriend" rips off their 1979 song "I Wanna Be Your Boyfriend." Lavigne denies all claims and is exonerated by the songwriters in 2008.
Lavigne and Whibley announce they are separating – on good terms. "We've been friends for a really long time, and we always will be," she says. "We're family and we have a connection." In the New Year, the exes work together on Lavigne's latest album, Pink Crust, which includes a song from Tim Burton's Alice in Wonderland.
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