Taylor Swift's Top 10 Biggest Career Moments

What better place to start than right at the beginning? Swift’ debut single “Tim McGraw” was released in June 2006. She reportedly conceived the idea for the song, inspired by her love for country star Tim McGraw, while daydreaming during math class. Swift then wrote it in about 20 minutes. Oh, and did we mention she was only fifteen at the time? Her self-titled debut album followed a few months later and also included the classic hits “Teardrops on My Guitar” and “Our Song”. It lived over three years on the Billboard 200 chart and was certified seven times platinum. All these years later, we sure are glad she was passionate about music and not trigonometry.

Taylor Swift and the Grammys are like peanut butter and jelly or cookies and milk; two things that just sort of go together and nobody really questions it. This loving and fruitful relationship started in 2010 when Tay Tay won the grammy for Best Female Country Vocal Performance for “White Horse” at the 2021 Grammys. That same night she also won Best Country Song for “White Horse” and Best Country Album and Album of the Year for “Fearless.” Taylor was also one of the night’s performers, singing alongside the incomparable Stevie Nicks. And 2010 was only the beginning. As of 2024, she has won 14 grammy awards out of 52 nominations and is the only artist to win Album of the Year four times.

There’s a cost to being a celebrity at the level of Taylor Swift. Your every move and every choice is heavily scrutinized and often criticized. This can lead to adverse consequences as Taylor reveals in the riveting and personal 2020 documentary “Miss Americana.” No topic is off limits as we’re taken on a journey covering Taylor’s career over the years, her first foray into politics, and her struggles with negative press, eating disorders, and mental health. All the while she is trying to discover who she is and what she stands for. We’re not all multi-platinum recording artists but this documentary shows us that if we all found our voices, the world would be better for it.

As of 2024, Taylor Swift holds the record for the artist with the most American Music Awards wins at a whopping 40 wins. A large part of that happened over one night with Swift winning six awards just during the 2019 AMAs. Those notably included Favorite Pop/Rock Album for “Lover" and Artist of the Year & Artist of the Decade for Swift herself. These awards allowed her to break the previous record of 26 wins held by the great Michael Jackson. In her acceptance speech, Swift expressed her desire to “create something that lasts.” Whatever the future holds, we’re confident she’s already done that.

Not a lot of people are able to sell out one or two stadiums, much less 36 stadiums across 7 countries. But Taylor Swift can. The Reputation Stadium Tour Kicked off in Arizona in May 2018 in support of her 2017 album with the same name. It ended six months later and included shows in Japan, Australia, Ireland, and New Zealand. The tour was noted for its use of the snake imagery during the performances building on the “Reputation” album theme. A supporting concert film: “Taylor Swift: Reputation Stadium Tour” was released on Netflix after being filmed at Arlington’s AT&T Stadium. The tour was highly successful, breaking attendance records, winning numerous awards, and generating nearly $350 million in revenue.

This lengthy version of the deeply personal fan favorite was initially developed while Taylor was on her “Speak Now” tour and finally released on “Red (Taylor’s Version)” a decade later. It became the highlight of the album with some critics calling it her best song yet. As of September 2024, it is the longest number one song in Billboard chart history. Taylor also stepped into the role of filmmaker when she wrote and directed “All Too Well: The Short Film” starring Dylan O’Brien and Sadie Sink. The video takes us on an electrifying journey of a relationship that spectacularly implodes and the female protagonist who has to get up and dust herself off. It won the Grammy, MTV VMA, and AMA Awards for Best Music Video.

The 2010s was a monumental decade for Taylor Swift. She released five albums, had multiple tours, successfully transitioned to pop music, won so many awards, and became one of the world’s biggest artists. In honor of all her accomplishments she was named Billboard’s first woman of the decade in 2019. In her acceptance speech, she reflected on her career while highlighting misogyny in the music industry and other challenges faced by artists and songwriters. We'll just add artist advocacy to the list of reasons we love her, along with great songs, awesome music videos, and an enviable knowledge of cat breeds.

Every year for nearly a century TIME magazine has crowned one individual their TIME Person (or Man/Woman) of the Year. This is their choice for the person who has had the most influence on society. In 2023, Taylor Swift became the first entertainer to receive this incredible honor usually given to heads of state, captains of industry, political activists, and the occasional Pope.
Among other factors, TIME cited Swift’s monumental success in the music industry and her ability to transcend borders and reach a global audience. In a world that is increasingly divided, one thing you can count on is that there are T-Swizzle fans everywhere.

In 2019, Scooter Braun acquired the rights to the masters of Swift’s first albums when he purchased her original label Big Machine Records, leading to a heated dispute between Braun and Swift. As a result, Swift decided to re-record those albums with the title “Taylor’s Version.” The albums would also include previously unreleased songs. As of August 2024, four re-recorded albums have been released. “Fearless (Taylor's Version)” and "Red (Taylor’s Version)” came out in 2021 followed by the Taylor’s Versions of “Speak Now" and “1989” in 2023. The albums defied all expectations and were a massive financial and cultural success. T-Swift was called 2021’s greatest Pop star and was praised for reclaiming ownership of her music and empowering other artists to do the same.

Before we unveil our top pick, here are a few honorable mentions:

Fearless World Tour
Her 1st Headlining Tour: Over 100 Shows in the US & Abroad

Dr. Swift
Swift Was Awarded an Honorary Doctorate of Fine Arts from New York University in 2002

One Million in One Week
“Speak Now” Sold 1 Million Units in Just 1 Week

Top Seller of the Year
“Fearless" Was 2009’s Best Selling Album

The Swifties
Taylor’s Fans Are Fiercely Loyal, Devoted, & Protective of Their Favorite Pop Princess

Taylor Swift was never one to keep things small but with some 150 shows in more than a dozen countries and five continents, the Eras Tour made everything that came before look like picnic acapella. It was a Herculean tribute to 17 years of music that combined epic choreography with intimate acoustic performances, all to rapturous fan applause. The tour made Taylor the first billionaire to “earn that status through music” and boosted economies around the world as politicians jockeyed to have Taylor perform in their cities. Fans who couldn’t make it or couldn’t get enough got the home experience with “The Eras Tour” film. While we have no doubt that Taylor is going on to bigger and better things, we are never ever ever getting over this tour.

Which of these phenomenal career moments resonated with you the most? What other Taylor-ific moments should have made the list? Let us know in the comments below.