'Oops! ... I Did It Again' (2000)
Spears' second album, Oops! ... I Did It Again, was released on May 16, 2000. It broke records by moving 1.3 million copies in its debut week. (The blockbuster single of the same name came out one month prior.) Here, Spears poses with her Oops!-inspired doll in October 2000.