'Look What You Made Me Do' singer who has won the most Billboard Music Awards (23)
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Related clues
- Only person in the arts ever to be named Time's Person of the Year
- Singer whose 2014 album "1989" had five songs top the Mainstream Top 40 chart
- Singer who was nominated for a Grammy for Best New Artist in 2008 but lost to Amy Winehouse
- 'Anti-Hero' singer who is nominated for a 2022 American Music Award for Artist of the Year
- She once sent a fan a check for $1,989 for college tuition, an echo of one of her album titles
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