2. Avril Lavigne
How you remember her: It was tough to forget the day that Avril Lavigne came into our lives with her super thick eyeliner and catchy songs about punk rock and skat8r bois. However, she was only 17 when she released Let Go, her very first album, so we can excuse the blatant lack of maturity. Other singles like “Don’t Tell Me” and “My Happy Ending” showed more depth, but not much. She married Sum 41’s Deryck Whibley in what ultimately wasn’t pop-punk matrimony, and, in a cringe-worthy moment of all cringe-worthy moments, was Nickelback leader Chad Kroeger’s wife for a while.
How you don’t want to remember her: That was around the same time that she gave us her self-titled album, which couldn’t even be saved with names like Marilyn Manson and Kroeger as contributors. Selling more poorly than any of Lavigne’s other body of work, she also caught some flak for the song “Hello Kitty,” which would have fit much better musically and lyrically on her first album. Oh yeah, and she got a few charges of racism thrown her way too. Fun.
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