Good move: Making friends with Mickey (1993)
In the early '90s, Disney became a breeding ground for young singers. Aguilera spent a year on the channel's Mickey Mouse Club, joining a roster that included Britney Spears, Justin Timberlake, J.C. Chasez and Keri Russell.
Good move: Letting the genie out (1999)
Showcasing her strong pipes, 18-year-old Aguilera debuted near the top of the charts with her self-titled first album. Her singles were at once suggestive ("Genie in a Bottle"), empowering ("What a Girl Wants") and romantic ("Come On Over Baby (All I Want is You)"). Unlike her teenybopper peers, Aguilera showed both sexiness and vocal prowess; the record sold eight million copies.
Bad move: No habla espanol! (2000)
Releasing a Spanish-language pop album is fine if you can actually speak the language. Aguilera, a Staten Island native with an Ecuadorian father and a mixed European mother, made the iffy "Mi Reflejo," featuring Spanish versions of her hits and a few new songs. The album seemed less about a love of her heritage and more about trying to make beaucoup bucks in a new target market.
Bad move: 'The Real Slim Shady' calls her out (2000)
In his breakout single from "The Marshall Mathers LP," Detroit rapper Eminem suggested Aguilera performed a particular sexual move on both MTV VJ Carson Daly and Limp Bizkit singer Fred Durst. Daly and Durst played along; meanwhile, Aguilera threw a hissy fit, prompting "the lady-doth-protest-too-much" responses.BACKNEXT