Taylor Swift Timeline: A Career In Albums


Taylor Swift announced her fifth studio album right on schedule.  Here’s a look back on the four albums and eras that defined Taylor.

1. Taylor Swift 


October 2006

Style: Country! Big hair, sweet sundresses and lots of lip gloss.

Singles: Tim McGraw, Teardrops On My Guitar, Our Song, Picture To Burn, Should’ve Said No

Taylor Swift broke onto the country music scene at the sweet young age of 16. Her family moved to Nashville, Tennessee, two years earlier to help Taylor star her career. Swift was one of the first artists signed to Big Machine Records.  She opened for Rascal Flatts, George Strait, Kenny Chesney, Tim McGraw with Faith Hill, as well as touring by herself. She won the American Music Award for Favorite Country Female Artist and was nominated for the Best New Artist Grammy in 2008.

Taylor sang songs about high school, boyfriends, small towns, and childhood. Songs about teenage angst like “A Place In This World” “The Outside”, and “Tied Together With A Smile” balanced out love songs like “Teardrops On My Guitar”, “Tim McGraw” and “Our Song”. Girls could relate. Taylor Swift was Taylor Swift’s most country album and introduced her as a cute, fearless teenage girl and wickedly talented songwriter.

2. Fearless


November 2008

Style: Fairy Tale Princess!  Dreamy dresses, romantic waves, light colors and metallics.  She wore a lot of Blumarine dresses.

Singles:  Love Story, You Belong With Me, White Horse, Fifteen, Fearless

These were the “Love Story” years. “Love Story” was the biggest and the most ubiquitous song of the next few years, to the point of obnoxiousness. When “Love Story” made it to the top of every list in America, “You Belong With Me” swept the nation. “You Belong With Me” won the VMA for for Best Female Video in 2009. Kanye West interrupted her acceptance speech in support of Beyonce’s “Single Ladies” video with the infamous words, “Imma let you finish…”

Taylor also got involved with the Disney clique during the Fearless years. She co- wrote “You’ll Always Find Your Way Back Home” and “Crazier” for The Hannah Montana Movie and sang “Fifteen” with Miley Cyrus at the 2009 Grammy Awards. Taylor also had a rumored romance with The Jonas Brothers’ Joe Jonas around this time. In 2010, Taylor made her film debut in the ensemble comedy Valentine’s Day as Taylor Lautner’s cheerleader girlfriend and recorded “Today Was A Fairytale” for the film’s soundtrack.

Fearless won Grammys for Album of the Year and Best Country Album in 2010. The single “White Horse” won Best Country Song and Best Female Country Vocal Performances. Swift received eight nominations.

Fearless takes the concept of teen girl to the max. “Love Story” put this album at the top of the charts and for a while, Taylor seemed like the princess of the music industry. She accepted each of her awards with humility and grace and always seemed genuinely shocked when she won. She looked beautiful on tour and on the red carpet and wore fairy- tale dresses every girl wishes they had a place to wear. Fearless balanced the naiveté of a fairy tale love story with the hurtful realities of teenage heartbreak, peer pressure and popularity. Taylor navigated her teenage years with grace and elegance.

3. Speak Now


October 2010

Style: Enchanted! Sparkly dresses, brighter colors.  Taylor transitioned from Barbie- worthy getups to sleeker styles.  She also started showing up with straight hair around this era.

Singles: Mine, Back To December, Mean, The Story Of Us, Sparks Fly, Ours.

By Speak Now, Taylor established a reputation as somewhat of a serial dater. Tabloids linked her to Joe Jonas, Taylor Lautner, John Mayer, Zac Efron and a slew of other boys. Songs on Speak Now seemed inspired more by fame and show business than the previous two albums with songs like “Mean”, “Better Than Revenge” and “Long Live”. Still, Taylor kept her trademark hopeless romantic imagination in songs like “Speak Now”, and “Enchanted”. Speak Now also featured a flair for drama, like in “Haunted”, “Back To December”, “The Story Of Us”, and “Dear John”.

The 111- date Speak Now tour grossed $123 million dollars and became one of the highest- grossing shows of 2011. Taylor wrote different lyrics on her left arm every night of the tour. There’s a complete list here. The tour provided material for Swift’s first live album, Speak Now World Tour: Live.

“Mean” won the Grammy for Best Country Song and Best Country solo performance. Taylor contributed two songs to T- Bone Burnett produced The Hunger Games soundtrack: “Safe and Sound” and “Eyes Open”. She wrote and recorded “Safe and Sound” with the indie band The Civil Wars and “Eyes Open” by herself.

Taylor Swift also started releasing fragrances around this era. She called the first Wonderstruck, after a term she coined in the song “Enchanted”.

Speak Now is a strong album. Every song except the contemplative “Never Grow Up” packs a punch. Speculation over who inspired what songs threatened to overshadow the album (blame it on “Back To December”), but the songs’ passion, energy and drama hold their own. This album felt more like Taylor’s diary specifically and less like the dairy of any teenage girl. The Speak Now years retained a darker, edgier version of Fearless’ magic, but reflected Taylor’s growing sense of maturity.

4. Red


October 2012

Style: Red lips, straight hair, hot pants.

Singles: We Are Never Ever Getting Back Together, Begin Again, I Knew You Were Trouble, 22, Everything Has Changed, The Last Time, Red

Taylor signaled the start of her departure from country with Red’s first poppy single, ‘We Are Never Ever Getting Back Together”. For Red, Taylor worked with pop producers Max Martin, Butch Walker, and Shellback, who also produce for Britney Spears, Weezer, Avril Lavigne, and Pink, collectively. Three of Red’s singles (“We Are Never Ever Getting Back Together”, “22”, and “I Knew You Were Trouble”) featured electronica beats previously unexplored by Taylor. Red also included duets with Ed Sheeran and Snow Patrol’s Gary Lightbody.

In 2014, Red was nominated for four Grammys including Album of the Year. The Country Music Association honored Taylor with a Pinnacle Award for a “unique level of success”. The only other Pinnacle Award recipient is Garth Brooks. Taylor performed at the 2013 Victoria’s Secret Fashion Show.

Taylor grew up on Red. She released a song called “22” and the number really says a lot about how far she’s come since “Fifteen” on Fearless. Her songs reflect a more grown- up respect for relationships (“State of Grace”, “Treacherous”) and battle scars from past experiences (“All Too Well”, “I Almost Do”). Yet somehow, Taylor managed to reach out and perfectly grasp what it’s like to be a 22- year- old female. Happy, free, confused, and lonely, miserable and magical. At the same time. The silly songs and the serious songs remind fans that while growing up can be hard, it can be a little silly, too.

Taylor Swift Bio

Here’s the adorable autobiography that was up on Taylor’s official website before it got replaced with some corporate babble about how famous Taylor is.

Hi, I’m Taylor. I love the number 13. I was born in December on a Christmas tree farm. I like imagining what life was like hundreds of years ago. I have blurry eyesight. My favorite thing in life is writing about life, specifically the parts of life concerning love. Because, as far as I’m concerned, love is absolutely everything.

I’m easily excited, thrilled, scared, and shocked. I’m 23 now, but I never stopped jumping up and down when something wonderful happens. My biggest fear is getting bad news. Or, letting someone down. I really love showing people what I meant when I wrote a song, so my shows are very theatrical. I knock on wood constantly. I have a cat named Meredith. She’s named after my favorite character on Grey’s Anatomy, and she’s fantastic. I live in Nashville, a magical land where 99% of the people are friendly and courteous drivers who let you in and don’t honk at you.

I go into a trance when I’m in an antique store. I don’t like it when something or someone turns out to be different than what you originally thought. Like when you’re shopping and you find a really cute dress, only to realize it’s actually a strange jumpsuit situation. But I mostly don’t like it when it happens with people. I love my friends and I’m always making new ones. I don’t really think you can ever stop making new friends or learning about as many new things as possible. I also don’t think you should ever take life so seriously that you forget to play.

Music has taken me all over the world, but the fans are the reason it’s been so magical. I’m so blown away by how nice they are to me. It’s strange to feel so understood by such a large group of people, but I love it. For the last two years, I’ve been working on an album called Red. I called it that because of the tumultuous, crazy adventures in love and loss that it chronicles. In my mind, when you experience love that’s fast paced and out of control and mixes infatuation, jealousy, frustration, miscommunication, and all of those lovely emotions… In retrospect, it all looks red.

I can’t wait for so many things. But mostly I can’t wait to see you, whether it’s in a crowd or a coffee shop. Thank you for listening, showing up, reading, and taking such good care of me.


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