The event that accompanied the first-ever Glamor Woman of the Year award was held at the Rainbow Room in New York City (via Glamour), a space Rockefeller Center calls “the original home of glamor and new-fangled entertainment.” Yorkers”. It was a fitting choice for 1990s cover star Madonna, who was the first person to receive the desired spot. Editor Ruth Whitney hailed Madonna’s longevity as a star, saying at the time, “Madonna always gets what she wants, always the best banana, always commander-in-chief of her own wildly successful company.” (by Glamour).
Madonna’s successful business continues to thrive, some 30 years after Whitney’s words were spoken in the Rainbow Room. Throughout the 1990s and early 2000s, the “Vogue” singer continued to make headlines for her professional endeavors. According to Billboard, Madonna essentially “reinvented” pop music in 2000, when she released a cover of “American Pie,” originally sung by Don McLean. The outlet notes that instead of being frustrated with the cover, McLean saw it as “‘sultry and mystical…a gift from a goddess.”
Her “goddess” status is likely what led to her significant inclusion as the Woman of the Year cover star, especially considering her philanthropic history in addition to her artistic career.