12 Milestone Taylor Swift Moments

Born in Reading, Pennsylvania on December 13, 1989, Taylor Alison Swift—named by her father after singer and songwriter James Taylor—has become a megastar across most music genres, a trajectory that started before she was even a teenager.

Within the past two decades, Swift’s career has slowly climbed from her earlier days jumping from writing her first song at 12 and releasing her debt at 16 to becoming the first female solo artist to win the Grammy for Album Of The Year three times, all the way through her recent record-breaking 2022 VMA win as a director and numerous accolades and honors to date.

In a career marked by dozens of remarkable milestones, here are 12 pivotal moments from Taylor Swift.

2001: Taylor Swift Writes Her First Song

In 2001, Taylor penned her first song, “Lucky You,” with the help of a local musician and computer repairman Ronnie Cremer, who also taught her how to play guitar.

2006: The Release of Taylor Swift

Performing at the Bluebird Cafe in Nashville, Swift grabbed the attention of record executive Scott Borchetta, who was then building Big Machine Records. Signed to the label, Swift released her self-titled debut and hit “Our Song,” which made her the youngest artist to write and perform a No. 1 track on the Billboard Hot Country Songs chart.

2007: Academy of Country Music Award Win for New Female Vocalist of the Year

Just one year later, a 17-year-old Swift won an Academy of Country Music Award for the Top New Female Vocalist of the Year. Making her debut at the awards show, Swift performed her debut single “Tim McGraw” in front of the country singer himself, who was in attendance. Though the song references McGraw, it was written about parting ways with a high school boyfriend who left for college.

But when you think Tim McGraw
I hope you think my favorite song
The one we danced to all night long
The moon like a spotlight on the lake
When you think happiness
I hope you think that little black dress
Think of my head on your chest
And my old faded blue jeans
When you think Tim McGraw

2009: CMA Entertainer of the Year

In 2009, Swift became the youngest person to ever win Entertainer of the Year at the Country Music Association Awards. “I will never forget this moment because in this moment everything I have ever wanted has just happened to me,” said Swift when she accepted the CMA award. That year, Swift also picked up a CMA for Album of the Year for Fearless and the Video of the Year Award for “Love Story.”

2009: Big Screen Debut

Swift made her big screen debut in the romantic comedy Valentine’s Day, playing Felicia Miller in 2010. The film, also starring Jessica Alba, Jessica Biel, Bradley Cooper, Jamie Foxx, Jennifer Garner, Anne Hathaway, Queen Latifah, Shirley MacLaine, Julia Roberts, and more, follows couples breaking up and getting together around Valentine’s Day. Swift also released a song for the soundtrack “Today Was a Fairytale,” and received a nomination at the 2010 MTV Movie Awards for the Best Kiss with her on-screen love interest Taylor Lautner. Swift briefly dated Lautner in 2009 and later wrote “Back to December” (off her third album Speak Now) about their relationship.

2012: ‘Pop’ Goes the Taylor with Red

By the age of 20, Swift already dominated country music and was ready to show her versatility as an artist and songwriter on the more pop-leaning tracks on her fourth album Red, with singles “I Know You Were Trouble,” “22,” and “We Are Never Ever Getting Back Together.” Her Red Tour was one of the highest grossing by a country artist and Swift also became the first female artist to sell out the Allianz Stadium in Sydney, Australia since it opened in 1988.

2014: 1989

Titled after her birth year, Swift’s next album, 1989, marked her full tilt into pop. More synth-pop than acoustic guitar, 1989 boasted hits “Shake It Off,” “Blank Space,” and “Bad Blood,” the latter track featured Kendrick Lamar, and a video featuring a “renegade” legion of women, including Selena Gomez, Cara Delevigne, Jessica Alba, Zendaya, and more.

2019: Lover and Republic Records

Her seventh album, Lover is Swift’s first release with Republic Records after her departure from Big Machine and was produced by Swift and Jack Antonoff, along with Joel Little, Louis Bell, and Frank Dukes.

2020: folklore and evermore

Produced by longtime collaborator Jack Antonoff, The National’s Aaron Dessner, and Joe Alwyn, Swift surprised everyone with the release of her eighth and ninth albums just five months apart from one another. Released July 24, 2020, the 16-track folklore is a collection of slow-burning indie-rock and folk narratives—written by Swift and a select group of co-writers, including Dessner and Antonoff—such as the moodier Americana track, “exile,” featuring Bon Iver (Justin Vernon), who also co-wrote the song. Upon its midnight release, the album broke the record for the biggest opening day on Spotify for a female artist, and folklore single “cardigan” marked Swift’s sixth No. 1 on the Billboard Hot 100. The album was also her seventh consecutive No. 1 on the Billboard 200, where it remained for eight weeks.

“In the past, I’ve always treated albums as one-off eras and moved onto planning the next one after an album was released,” Swift posted on social media. “There was something different with folklore. In making it, I felt less like I was departing and more like I was returning.”

Released later in the year on Dec. 11, the lush arrangements of evermore, produced by Swift, Antonoff, Aaron Dessner, and Bryce Dessner, blended alt-rock, chamber pop, and folkier, guitar-picked elements. The title track brings back Bon Iver, along with other Evermore guests, Haim, on “no body, no crime” and The National on “coney island.”

2021: Taylor’s Versions

Released on April 9, 2021, Fearless (Taylor’s Version), a re-recording of her second album is the first in a series of re-recorded albums planned for release by Swift, following the dispute around the ownership of the masters to her first six studio albums with her former label Big Machine Records.

2022: The ‘Swift’ School of Songwriting

On the heels of the New York University course on Taylor Swift and the trajectory of her power within the music industry, the University of Texas at Austin launched a new course, starting in fall 2022, focused on Swift’s craft as a songwriter.

“Swift draws on richer literary traditions in her songwriting, both topically but also formally in terms of how she uses references, metaphors, and clever manipulations of words,” said Professor Elizabeth Scala, who will teach “The Taylor Swift Songbook” to undergraduates in the Liberal Arts Honors program. “I’ll be showing students that these operations and interpretive moves one makes when reading her songs are appropriate to all forms of writing.”

2022: Making VMA History

Swift recently made history again at the 2022 MTV VMAs when she took home five awards, including Video Of The Year, Best Long-Form Video, and Best Direction, for “All Too Well (10 Minute Version) (Taylor’s Version),” an unabridged version of the song with melodies and verses that were removed from the original version on 2012 release Red.

Not only is she the only woman to ever win three Album of the Year Grammy awards, but Swift is also the first female to win three VMAs for Video of the Year, for “Bad Blood,” “You Need to Calm Down,” and now, “All Too Well.”

Photo by Dimitrios Kambouris/Getty Images for The Rock and Roll Hall of Fame