Possible Clues:

• Superstar provides heavenly bread stuffed with delicious olive tips
• Crazy about new American singer
• The top Hot 100 solo artist of all time, per Billboard
• Yuletide stamp portrait
• Singer/actress known as the "Queen of Pop"
• Singer/actress known as the 'Queen of Pop'
• Mother figure spreading heavenly food around party
• Top-selling female recording artist of all time, per Guinness
• One-named singer called the 'Queen of Pop'
• Singer retired in the year daughter and American married