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2004 · Business
Signs with Big Machine Records
After years of Nashville songwriting rounds, she signs as the label's first artist.
2006 · Music
Taylor Swift released
Debut studio album; establishes her as a self-written country-pop singer-songwriter.
2008 · Music
Fearless released
Crossover breakthrough; becomes the best-selling album of 2009 in the US.
Apr 23, 2009 · Tour
Fearless Tour begins
Her first headlining tour, opening in Evansville, IN.
Jan 31, 2010 · Award
Wins her first Grammy for Album of the Year
Fearless wins AOTY, making her the youngest solo artist to win the award at the time.
2010 · Music
Speak Now released
Every track solo-written; wins Album of the Year at the Grammys the following year.
Feb 9, 2011 · Tour
Speak Now World Tour begins
Her first tour built around a fully solo-written album.
2012 · Music
Red released
Major sonic pivot toward pop; "We Are Never Ever Getting Back Together" becomes her first Hot 100 No. 1.
Mar 13, 2013 · Tour
Red Tour begins
Opens in Omaha, NE; her first tour to play stadiums on select dates.
2014 · Music
1989 released
Full pop reinvention; wins Album of the Year at the Grammys.
May 5, 2015 · Tour
The 1989 World Tour begins
Opens in Tokyo; becomes the highest-grossing tour of 2015.
Feb 15, 2016 · Award
Wins her second Grammy for Album of the Year
1989 wins AOTY.
2017 · Music
reputation released
Reinvention era following a period of intense media scrutiny.
May 8, 2018 · Tour
reputation Stadium Tour begins
Opens in Glendale, AZ; becomes the highest-grossing US tour of all time at the time.
Dec 31, 2018 · Creative Work
Reputation Stadium Tour concert film released
Premieres on Netflix, capturing the tour's Levi's Stadium shows.
2019 · Business
Lover released; masters dispute becomes public
Sale of her back catalog's master recordings sparks the re-recording project.
Jan 23, 2020 · Creative Work
Miss Americana premieres
Netflix documentary opens the 2020 Sundance Film Festival.
2020 · Music
folklore & evermore released
Surprise sister albums; major stylistic pivot into indie-folk songwriting.
Nov 25, 2020 · Creative Work
folklore: the long pond studio sessions released
Disney+ special documenting the album's writing and recording with Aaron Dessner and Jack Antonoff.
Mar 15, 2021 · Award
Wins her third Grammy for Album of the Year
folklore wins AOTY.
2021 · Business
Fearless (Taylor's Version) released
Apr 9 — first re-record, with 6 From the Vault tracks; the project to reclaim her catalog begins in earnest.
Nov 12, 2021 · Business
Red (Taylor's Version) released
Includes the 10-minute “All Too Well” and 9 From the Vault tracks.
Nov 12, 2021 · Creative Work
All Too Well: The Short Film premieres
Written and directed by Taylor, starring Sadie Sink and Dylan O'Brien; released the same day as Red (TV).
2022 · Music
Midnights released
Record-breaking streaming debut; sweeps all top 10 Billboard Hot 100 spots.
May 18, 2022 · Award
Receives honorary doctorate from NYU
Delivers the commencement address at Yankee Stadium.
Mar 17, 2023 · Tour
The Eras Tour begins
Tour opens in Glendale, AZ; becomes a defining cultural & commercial event.
Jul 7, 2023 · Business
Speak Now (Taylor's Version) released
6 From the Vault tracks, including “Electric Touch” feat. Fall Out Boy.
Oct 13, 2023 · Creative Work
Taylor Swift: The Eras Tour concert film released
Theatrical release; becomes the highest-grossing concert film of all time.
Oct 27, 2023 · Business
1989 (Taylor's Version) released
5 From the Vault tracks, including “Is It Over Now?”
Feb 4, 2024 · Award
Wins a record fourth Grammy for Album of the Year
Midnights wins AOTY — no other artist has won it four times.
2024 · Music
The Tortured Poets Department released
Massive streaming/chart impact; Eras Tour continues into its final legs.
2025 · Music
The Life of a Showgirl released
Latest studio album; expands the discography as the Eras era closes out.
Dec 12, 2025 · Creative Work
The End of an Era & The Final Show released
Behind-the-scenes docuseries and a second concert film from the Eras Tour's Vancouver closing shows, both on Disney+.