In 1999 , Ross was named the most successful female singer in the history of the United Kingdom charts , based upon a tally of her career hits . Madonna would soon succeed Ross as the most successful female artist in the UK . Later that year , Ross presented at the 1999 MTV Video Music Awards in September of the year and shocked the audience by touching rapper Lil ' Kim 's exposed breast , pasty-covered nipple , amazed at the young rapper 's brashness
1999 MTV Video Music Awards
1999 MTV Video Music Awards
Diana Ross