One of the wildest, strangest and most inventive hip hop singles of the last decade, "Work It" laid the groundwork for future rap sounds while also tipping its Kangol to the old school via a tasty Run DMC sample. Incredibly, it never hit No. 1, and is tied with Foreigner's bland 1981 hit "Waiting for a Girl Like You" for the lengthiest stay (10 weeks) at No. 2 without hitting No. 1.

- Dave Lewis