September 7, 2008 - Kevin Winter/Getty Images North America more pics like this »
9. Ups and Downs

Despite some pretty ugly events in her social life (losing custody of her kids, being placed under a conservatorship, landing in a psychiatric ward briefly, not to mention shaving her head), Brit continued to dazzle fans with her music. She won Best Female Video, Best Pop Video, and Video of the Year for "Piece of Me" at the 2008 MTV VMAs (seen here) and released her sixth album, Circus, in December of that year.