Taylor Swift has won 10 Grammys over the course of a career spanning almost 15 years thus far. She’s nominated three more times this weekend, bringing her grand total to 35 bids. But what are the best songs of her career? Click above for our countdown of her top 21 greatest hits. Does your favorite song make the cut? Do you agree with our pick for number-one? Let us know in the comments.
Swift has been a music star for about half of her life. She was only 16 when her self-titled debut album was released in 2006. That country collection was certified seven-times platinum by the Recording Industry Association of America (RIAA) for its massive sales, and it earned her a Grammy nomination for Best New Artist. She lost to the Amy Winehouse. But it was her next album that exploded her career.
“Fearless” was released in 2008, and it earned her eight Grammy nominations when it was eligible in 2010. She ended up winning four of those, including Album of the Year and Best Country Album. She was only 20 when she took the top prize, which made her the youngest artist ever to win that award, sliding in under Alanis Morissette, who was 21 when she prevailed for “Jagged Little Pill” in 1996. That record still stands, though it could be broken this weekend by 18-year-old Billie Eilish.
Swift was always a crossover success, straddling the line between pop and country throughout her career, but she made a formal break from country music with her 2014 album “1989,” which was a successful play for pop supremacy, winning her another Grammy for Album of the Year. That was historic too: she was the first woman to win that category twice as a lead artist.
So Swift’s hits span genres and subjects — ballads about finding love, confessionals about love gone wrong, telling her haters in the media and industry to shove off, or shaking it off if they don’t. She’s got a long list of ex-lovers — and a current “Lover” — but which of her songs do you love the most?
Be sure to make your Grammy predictions so that record executives and top name stars can see how their music is faring in our Grammy odds. Don’t be afraid to jump in now since you can keep changing your predictions until winners are announced. And join in the fierce debate over the 2020 Grammys taking place right now with Hollywood insiders in our music forums. Read more Gold Derby entertainment news.