6. 504 Boyz "Wobble Wobble" (2000)
Really, The Showboys' "Drag Rap" (also known as the "Triggerman" beat) is the original twerking anthem—a one-off New York rap single that became a regional hit 1,300 miles away in New Orleans—and its role as a sample in the 504 Boyz "Wobble Wobble" was key to the song's charting success. In 2000, the year it was released, the track fought against all market trends (No Limit had fallen on hard times since most of the label's artists defected) and hit No. 17 on the Hot 100. Also, it's a scientific fact that the gluteal muscles respond particularly well to keyboard emulations of marimba tones.* Of note: This was a particularly groundbreaking work for popularizing the titular synonym for 'twerking.'
[*Not actually a scientific fact, but you get the idea. That said, we imagine twerking as your sole exercise routine is exponentially better than no exercise. Ratchet, sure. But healthy? Absolutely.]