November 16, 2003 - Frank Micelotta/Getty Images Entertainment more pics like this »
3. Winner Winner

Britney performed in this hot ensemble at the 2003 American Music Awards. She was back to focusing on her pop career at this point after opening a restaurant called Nyla in NYC and trying her hand at acting in the flick Crossroads in 2002. Neither endeavor led to much, so she stuck to music in 2003.