Janet Jackson- If 
Choreographed by Tina Landon
This video and dance sequence are so important and legendary it makes me emotional.
Per Wikipedia: “The choreography performed in “If,” specifically the main dance breakdown, garnered acclaim for its complexity, also regarded as “iconic” and “ground-breaking.”
"The video was also praised as featuring "some of the most iconic choreography in history," adding "it’s stunning imagery, ground-breaking choreography and Janet’s fierce attitude is what made this a masterpiece."
"If" is one of several of Jackson’s videos considered to influence a higher degree of sexual freedom among young women…with Jackson "heavily implying male-on-female oral sex in music videos by pushing down on a man’s head until he’s in exactly the right position."
Latoya and Janet
Janet Jackson accepting the MTV Movie Award for best female performance in Poetic Justice, in 1994
Janet Jackson | Miss Jackson | Rhythm Nation 1814 | VMA 1990 | Iconic performance of Black Cat