Taylor Swift (Eras Tour)

The Untold Story: Taylor Swift’s Journey from Small Town Girl to Superstar!

By: Matt

Today, Taylor Swift is among the highest-earning musicians of all time. Known for producing catchy mega-hits and stripped-down tunes anyone can connect with, Taylor is a force to be reckoned with in the entertainment industry. She has a massive fan base that continues to propel her down a path of superstardom and plenty of talent to achieve impressive longevity in a world always looking for the next best thing.

While most know Taylor Swift today for her surprise albums, revealing lyrics and blockbuster stadium tours, she was once just a small-town country girl wiping away the teardrops on her guitar. Her meteoric rise to fame is nothing short of awe-inspiring, and fans continue to get blown away by her never-ending quest to do more.

Taylor Swift revolutionized what it means to be an “artist.” Her career is a masterclass in creativity, entrepreneurship and pure badassery! Let’s take a look at Taylor Swift’s journey thus far.

The Early Years

Young Taylor Swift

The superstar we know today had humble beginnings. Taylor Alison Swift was born on December 13th, 1989 (a year that would become even more defining later in her life). She was born in Reading, Pennsylvania, to Scott and Andrea Swift. She also has a little brother, Austin.

Taylor spent her earliest years on her family’s Christmas tree farm, spending summer vacation in Stone Harbor, New Jersey. While Taylor’s many hobbies included horseback riding, she followed in her grandmother’s footsteps, who was a professional opera singer.

By 10, Taylor was singing in coffee shops and fairs. She even sang “The Star-Spangled Banner” at a 76ers game when she was 11! At 12, she began learning guitar and writing songs.

Taylor’s Big Break

Taylor and her family frequently traveled to Nashville to submit demo tapes. In 2003, she began working with a talent manager who secured her modeling gigs with Abercrombie & Fitch.

Her manager also helped her land an opportunity to perform original songs at an RCA Records showcase. That break helped her sign an artist development deal, and the family ultimately moved to Hendersonville, Tennessee, to be closer to Nashville.

In 2005, Taylor performed at an industry showcase in the Bluebird Cafe. There, she captured the attention of Scott Borchetta, who was launching an independent music label. Taylor Swift was among the first artists to sign with the new label, called Big Machine Records. 

This event started it all, and Taylor began writing her first album.

2006: a Self-Titled Debut

big machine records taylor swift

2006 introduced the world to Taylor Swift with her self-titled debut album. Taylor wrote or co-wrote all tracks, an approach that would follow Swift throughout her career. The first single of “Taylor Swift” was “Tim McGraw.”

Because Big Machine Records was still a newcomer, Taylor and her mother worked hard to promote the album and send single CDs to country radio stations.

Taylor spent 2006 to 2008 promoting her debut, releasing four more singles. These included “Teardrops on My Guitar,” “Our Song,” “Picture to Burn” and “Should’ve Said No.” Swift got tons of exposure and opened for huge country acts like Faith Hill, Rascal Flatts, Tim McGraw, and more. Her debut peaked at number five on the U.S. Billboard 200.

Country Success

Taylor’s debut album earned her considerable attention in the country scene. As a blond-haired, blue-eyed young girl, she was easy to love. She made a huge name for herself during her first album cycle, eventually winning her first CMT award at 18.

2008: a “Fearless” Number One

“Fearless” came out in the tail-end of 2008, and it was even bigger than her debut! The second album became her first number-one, claiming the top spot for 11 weeks. It became the longest-running number-one album for a country female artist in history.

This album gave Swifties classics like “White Horse,” “Fearless,” and “You Belong with Me.” The latter was a crossover smash, giving Taylor a taste of pop stardom while still dominating the country genre.

This album led to many awards, earning Taylor her first three Grammy Awards. 

The Incident

Despite all the success, Taylor’s journey through the “Fearless” era wasn’t without drama. During the 2009 MTV VMA Awards, Taylor won the award for “Best Female Video.” But during her acceptance speech, Kanye West infamously interrupted her with the “Imma let you finish…” speech.

The hotly debated moment became a sour point in Taylor’s career that would resurface many years later. However, many argue it was also a moment that would define Swift’s public image moving forever, for better or worse.

2010: The “Speak Now” Era

Taylor Swift Speak Now

2010 saw the release of Taylor’s third album, “Speak Now.” This album gave the world great chart-toppers like “Dear John,” “Back to December,” and “Mean.” Even more awards followed. In addition to more Grammys, Taylor won “Woman of the Year” from Billboard, “Entertainer of the Year” by the Country Music Association and more.

To support the album, Taylor went on a 15-month world tour. She also got into acting, playing a part in the film “Valentine’s Day.”

A Tabloid Darling

During this time, Taylor Swift became the topic of tabloid fodder. Taylor has had many high-profile relationships throughout her career. Because Taylor is a songwriter, tabloids and fans alike frequently speculated about the behind-the-scenes events of some of her relationships.

While Taylor never truly speaks about the subjects of her songs, many fans connect the dots to famous exes like Joe Jonas, Taylor Lautner, Conor Kennedy, Jake Gyllenhaal and Harry Styles.

2012: Seeing “Red”

2012’s “Red” album was a departure for Taylor Swift. Up to that point, she was squarely a country artist. Crossover hits helped push her into the pop mainstream, but many regarded her as a country singer and songwriter. That changed with “Red.”

Taylor worked with producers like Shellback and Max Martin, making “Red” a beautiful mix of country and pop. It featured singles like “22,” “All Too Well,” and “We Are Never Ever Getting Back Together.” The album won numerous awards and spawned “The Red Tour,” the highest-grossing country tour at the time.

A Feud for the Ages

The Kanye incident wasn’t the last time Taylor would be involved in a celebrity feud. Taylor would get into a long-standing tiff with former friend Katy Perry, allegedly over Perry attempting to “sabotage” Swift’s tour by hiring dancers and crew from under her.

Whether or not any of that is true is up for debate, but the feud spawned tons of drama and inspired future works by both artists. The two eventually made up, but not before fans took sides, and both singers took shots through song.

2014: Pop Perfection and “1989”

taylor swift Shake It Off

Many Swifties regard “Red” as a transition album. It had many pure pop tracks, but the collective was a marriage of country and pop. “1989,” however, was all pop! It was Taylor’s official transition into the pop genre, something she continues to this day.

The album was a smash, selling over 10 million copies. It marked a shift in the singer’s artistry and style, spawning amazing singles and music videos like “Shake It Off,” “Blank Space,” and “Bad Blood,” a song allegedly about the Katy Perry feud.

The World’s Newest Pop Princess

“1989” wasn’t just a sonic shift. This era was one of pure pop domination! Not only did Taylor produce some inspiring visuals for every single, but she also made countless appearances.

Some highlights include a show-stopping performance at the Victoria’s Secret Fashion Show, a star-studded cast of famous friends in the “Bad Blood” music video, a hugely popular single for the “Fifty Shades Darker” film and more.

Taylor the Entrepreneur

Taylor’s entrepreneurial finesse was another notable “1989” era highlight. Taylor got into a public fallout with popular streaming services like Spotify and Apple Music. Swift pulled her entire catalog from Spotify due to its low artist pay, arguing that many up-and-coming artists were being devalued. 

She also threatened to do the same with Apple Music because it didn’t pay artists during its free trial period, but the tech giant caved and changed its policy in response.

The Incident: Part 2

Remember Taylor’s Kanye incident? It continued in 2016 when West released the track “Famous.” It included a controversial line about Taylor Swift. Taylor spoke out about it, and West’s then-wife, Kim Kardashian, released videos of Kanye and Taylor discussing the track over the phone.

The fallout was quick and fierce. Many people on the Internet attempted to “cancel” her. During that time, she was also dealing with a lawsuit from a former disc jockey whom Taylor accused of groping her many years ago. Taylor counter-sued the jockey for sexual assault, winning a symbolic judgment of $1.00.

The Kim Kardashian drama, paired with the lawsuit, put Taylor in a precarious position, and it would go on to dictate her artistic and personal direction.

A Break from the Limelight

The backlash from the Kim/Kanye saga made Taylor a massive target for online harassment. Millions flooded her social media profiles with snake emojis.

The experience forced Taylor to take a step back from the limelight. She spent more time away from celebrity life, a stark departure from her “1989” era. While Swifties eagerly awaited her return, Taylor quietly crafted her next masterpiece.

2017: A Challenging “Reputation” and a Savage Comeback

Taylor Swift released her sixth studio album, "Reputation," in 2017

Taylor Swift released her sixth studio album, “Reputation,” in 2017. It was another sonic departure from the pop bliss of “1989.”

Instead of upbeat tracks full of gloss, “Reputation” was an introspective look at the impact of fame. It mixed electropop sound with hip hop and R&B, spawning singles like “Look What You Made Me Do” and “…Ready for It?”

The album was an ode to the haters, and Taylor’s style was noticeably darker than previous eras. The album was edgy and fun, showing who Taylor is.

A London Romance

Behind the scenes, Taylor was in a long-term relationship with Joe Alwyn. Unlike past relationships, this one was kept well under wraps. Both Alwyn and Swift didn’t speak publicly about the relationship, but it inspired Taylor’s next album.

2019: A New Label and “Lover

Departing from the edginess of “Reputation,” Taylor’s next album was full of love, hope and light. “Lover” was released to much acclaim and became Swift’s fastest-selling album.

It was unique because it wasn’t released under Big Machine Records. After 13 years and six groundbreaking albums, Taylor signed a new deal with Republic Records, a part of Universal Music Group.

Many initially saw the new deal as a standard boilerplate music business event. However, it was just the start of Taylor’s biggest drama yet.

Taylor Takes Control

Taylor became involved in a very public feud with talent manager Scooter Braun. Scooter purchased Big Machine Records, subsequently owning the masters of Swift’s original six records.

taylor swift scooter braun

According to Taylor, she tried to buy her masters from Big Machine Records before the sale, but the label attempted to use them as a bargaining chip to sign a new deal. Taylor refused, and Scooter Braun became the owner of her masters in 2019.

While most artists would shrug their shoulders, Taylor took a stand. She announced that once she was legally allowed to, she would re-record her previous work to regain ownership of her life’s work. It’s a clever workaround that shocked the music industry. She gained much peer support, and the dispute caused rippling changes across the industry.

Many labels began to include stipulations preventing re-recordings like this, and other huge artists have begun re-recording projects thanks to Taylor’s inspiration.

Miss Americana

In 2020, “Miss Americana hit Netflix and select theaters. This documentary film covered Taylor’s life between the “Reputation” stadium tour and the rollout of the “Lover” album.

It offered a rare glimpse into the real life of Taylor Swift, covering the good, the bad and the ugly. While Taylor is known for being open with fans through her music and artistry, the documentary uncovered personal struggles the world never knew about.

It’s a hallmark moment in her career and a project that many cite as a reason for having such a strong connection with Taylor.

2020: The “Folklore” and “Evermore” Surprise

taylor swift folklore

2020 saw not one but two albums from Taylor! The first was “Folklore,” an indie-rock and alternative album. The second came less than five months later. Titled “Evermore,” it was a surprise continuation of “Folklore.”

While these two albums are polarizing, they’re an important entry into the Taylor Swift discography. They offer a “realer” look into the artist, away from the glitz and glam of fashion. The albums are a return to form, showcasing Taylor’s artistry as a musician and storyteller.

The Birth of “Taylor’s Version

In 2021, Taylor Swift was legally free to start releasing her re-recorded albums. She began with “Fearless” and “Red,” both released in 2021.

Taylor did more than re-record her albums verbatim. These albums, dubbed “Taylor’s Version,” also included unreleased “tracks from the vault.”

The albums are more expansion than the original work, including unreleased B-sides and new versions of the tracks Swifties love. Many also included new features from artists like Ed Sheeran, Chris Stapleton and more. 

2022: “Midnights” and World Domination

taylor swift midnights

2021 and 2022 were busy years for Taylor Swift! Not only did she spend significant time in the studio re-recording her back catalog, but she also crafted her next album. 

“Midnights” was released in 2022. It was fittingly released at midnight. However, a surprise “3 A.M. Edition” launched several hours later.

This release was huge. It spawned widely popular singles like “Anti-Hero” and “Karma.” Taylor monopolized the Billboard Hot 100 chart upon its release, taking all 10 top spots!

The “Eras Tour” Global Takeover

Taylor embarked on “The Eras Tour” in 2023. Instead of simply supporting the new “Midnights” album, this massive show showcased her entire body of work. It was yet another genius move from Taylor, the entrepreneur.

The tour coincided with additional “Taylor’s Version” releases, allowing the new tour to market both her latest work and her re-recordings.

This tour broke several records, including the most concert tickets sold in a single day. It became the highest-grossing concert ever, bringing in over $1 billion. The accompanying concert film also became the highest concert film in history, earning a Golden Globe Award!

America’s Sweetheart: The Redux

Thanks to “The Eras Tour” and the re-recordings, Taylor experienced a brand-new career high. She overcame the reputational damage of her post- “1989” era and came out on top amidst her highly publicized legal battles.

Taylor Swift mania is in full swing, and many consider her America’s sweetheart. After starting a relationship with Kansas City Chiefs tight end Travis Kelce, she’s returned to that all-American image.

She continued to win countless awards and receive massive attention from politicians, news outlets, tabloids and more. But unlike last time, this attention isn’t phasing her, and she’s already moving on to the next big thing.

2024: “The Tortured Poets Department”

the tortured poets department taylor swift

Taylor Swift continues her streak of success with “The Tortured Poets Department,” her 11th studio album. Like with “Midnights,” Taylor released an additional volume of music hours later, resulting in a double album dubbed “The Anthology.”

It debuted at number one and took the top 14 spots on the Billboard Hot 100 charts.

What’s Next for Taylor Swift?

As you can see, Taylor has had a crazy journey to the top. Despite several low points and career missteps, you can’t keep Miss Swift down! When many thought she was down, out and over, Taylor returned with a tour de force of talent and artistry.

The crazy thing? Taylor’s only 34! She’s already accomplished more in her career than most would dream of. Where will her career take her next?

You May Also Like