Inside Madonna's Most Significant Magazine Cover

The event that accompanied the very first Glamour Woman of the Year award was held at the Rainbow Room in New York City (via Glamour), a space that Rockefeller Center calls "the original home of New York glamour and entertainment." This was a fitting choice for 1990's cover star Madonna, who was the first person to receive the desired spot. Editor-in-chief Ruth Whitney praised Madonna's longevity as a star, stating at the time, "Madonna is still getting what she wanted, still top banana, still commander in chief of her own wildly successful enterprise," (per Glamour). 

Madonna's successful enterprise continues to thrive, some 30 years after Whitney's words were spoken at 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 by the cover, McLean regarded it as ""sensual and mystical ... a gift from a goddess." 

Her status as a "goddess" is presumably what led to her significant inclusion as the Woman of the Year cover star, especially when you consider her philanthropic history in addition to her artistic career.