Britney Spears- “Satisfaction”/ “Oops I Did It Again” (2000)
Britney Spears has continued the legacy of Madonna and has been the face of the VMAs for her generation. She has performed on the VMA’s 5 times, starting in 1999, with each performance more exciting than the last, except for that trainwreck in 2007. Of all her showings, “Satisfaction”/ “Oops I Did It Again” is most unforgettable because of the moment where she strips down into seemingly nothing and danced for her life. Jaws dropped. Yes, she sounded like her vocal cords had been run through a meat grinder until the pre-recorded vocal kicked in, but still, amazing nonetheless.