20. Celine Dion: $800M, My Heart Will Go On
Celine Dion possesses one of the most recognizable voices in music history. The Canadian singer’s career spans over four decades, with My Heart Will Go On from Titanic becoming one of the best-selling singles ever at over 18 million copies. She’s sold more than 200 million records globally and completed a Las Vegas residency that grossed over $680 million, making her one of the highest-grossing live performers of all time.

Recently, Dion revealed her diagnosis of Stiff-Person Syndrome, a rare neurological disorder causing severe muscle spasms. Despite this challenging health condition, she continues inspiring fans with her strength and grace. At 56, her approach to beauty has always prioritized authenticity over artifice. When photographed without makeup during rare casual outings, her bone structure and elegant features remain striking, though she’s naturally embraced the aging process with visible lines and wrinkles. She’s discussed how her late husband René Angélil encouraged her to be herself, which influenced her comfort with minimal makeup in private life. Her recent health struggles have understandably affected her appearance, yet she faces her condition with courage and openness. She represents a generation that’s learning to age publicly with dignity, showing that beauty evolves but doesn’t diminish with time or health challenges.