64. Too $hort "Freaky Tales" (1988)
Producer: T. Bohanon, Too Short
Album: Born To Mack
Label: Dangerous Music, Jive, RCA
$hort found a winning recipe and stuck with it—slow 808 beats, keys, and extra deep bass, leaving plenty of room for his conversational pimp talk. As an early regional rap pioneer, $hort catered to his audience who needed music to drive to rather than beats for the boombox or Walkman. "Freaky Tales" became such an iconic track for $hort that he released a sequel soon afterwards and even dropped a remake in 1995 called "Cocktails" with a new beat.
Related: Too $hort Breaks Down His 25 Most Essential Songs