It’s hard to remember a time in music before Taylor Swift. The singer-songwriter emerged on the scene with the release of her debut track, “Tim McGraw,” on June 19, 2006. A lot has changed since then, including her musical genre of choice. (Goodbye, country! Hello, pop!) To celebrate the re-recording of Taylor’s 2008 album “Fearless” — “Fearless (Taylor’s Version)” drops April 9, 2021 — Wonderwall.com is taking a look back at her many career highs, the few lows, the milestones and the dramas. Keep reading for more…
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Taylor Swift was far from an overnight success. The Pennsylvania native fell in love with country music as a tween, and when she was 11, Taylor and her mom went to Nashville to submit her singing demos to record labels. Rejections came pouring in, and Taylor decided she needed to write and perform her own songs. Three years later, at 14, she became the youngest songwriter ever signed by the Sony/ATV Tree publishing house. Then, in 2005, she was one of the first signings to country music label Big Machine Records.
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Taylor Swift was just 16 when she released her eponymous debut album in October 2006. Written almost single-handedly by Taylor during her freshman year in high school, the earnest album focused on young love and teen angst. “Taylor Swift” received rave reviews from critics, and the budding songstress quickly became the toast of the country music scene. In fact, with the album’s third single, “Our Song,” Taylor became the youngest artist in history to have written and performed a No.1 song on the Hot Country Songs chart.
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It wasn’t long before the awards started flooding in. At the 2007 CMA Awards, Taylor Swift won the coveted Horizon Award, which honors the best new country artist of the year. “I can’t even believe that this is real,” she said during her endearing acceptance speech. “I want to thank God and my family for moving to Nashville so I could do this. The fans — you have changed my life. This is definitely the highlight of my senior year!”
We’ve become accustomed to seeing Taylor Swift’s surprised faces at award shows, but it was especially exciting to see her response to getting a Grammy nod for best new artist. While helping to present the nominees for the 2008 show, she heard Dave Grohl and Taylor Hawkins of the Foo Fighters announce her name, and she ran right over and hugged them. “Don’t worry, Taylor,” Dave said. “You got it in the bag.” Alas, she didn’t — Amy Winehouse beat her out for the award.
Taylor Swift gave us a second helping of her musical stylings in November 2009 with her sophomore album, “Fearless.” While still a country record, the album also had mainstream pop appeal and marked the beginning of her crossover. Like with her debut album, Taylor either wrote or co-wrote every track on the album. This time, however, she also acted as co-producer. Buoyed by hits like “Love Story” and “You Belong With Me,” the album’s success bled into the following year, and by the end of 2009, “Fearless” was the top-selling album of the year.
It was the interruption heard ’round the world. At the 2009 MTV Video Music Awards, Taylor Swift was on stage accepting the Moonman for best female video for “You Belong With Me” after beating out the likes of Beyonce, Lady Gaga and Katy Perry. But before she could enjoy the moment, Kanye West crashed the stage, grabbed the mic, and said, “Yo, Taylor, I’m really happy for you, I’mma let you finish, but Beyonce had one of the best videos of all time!” A shocked Taylor simply stood by and watched as Kanye epically ruined her moment. Later that night, when Beyonce won video of the year, Bey called Taylor up and let her make her speech. “Maybe we can try this again,” Taylor said. Taylor and Kanye later buried the hatchet only to feud again in February 2016 when he released the song “Famous” — in which he raps, “I feel like me and Taylor might still have sex / I made that b**** famous.” Taylor has gone on to win 10 more VMAs.
Taylor Swift did double duty when she appeared on “Saturday Night Live” in November 2009, acting as both host and musical guest. Most memorable was her musical monologue in which she riffed on loving sparkly dresses, getting interrupted by Kanye West at the VMAs and having high-profile relationships. However, “SNL” wasn’t Taylor’s acting debut. Earlier that year, she played a murder victim on an episode of “CSI.”
Taylor Swift closed out the year by sweeping the 2009 Country Music Association Awards, taking home all four of the awards she was up for. Along with album of the year, female vocalist of the year and music video of the tear, Taylor won entertainer of the year, making her the youngest artist to win the show’s most sought-after prize. “I will never forget this moment because in this moment everything I have ever wanted has just happened to me,” she said as she accepted the award.
Taylor Swift put her 2008 Grammy best new artist loss behind her when she took home a whopping four wins out of eight nominations in 2010. (She may say 13 is her lucky number, but we’d argue it’s actually four.) If that wasn’t enough, Taylor also made Grammys history when she became the youngest artist to win the show’s top prize, album of the year. “Country music is my home,” Taylor told reporters later in the press room. “Country music is my love. But to have it organically crossover this year? It’s just been fantastic. I think the healthiest thing you can do when making music is remove stereotypes from it.”
In 2010, Taylor Swift proved that she wasn’t just popular but also powerful when she was named to the Time 100, Time magazine’s list of the most influential people in the world. She made the prestigious list again in 2015.
Taylor Swift made her big-screen acting debut in 2010 when she appeared alongside a slew of other stars in the rom-com “Valentine’s Day.” Although the movie was panned by critics, it was a box office success.
Taylor Swift was back with new music in 2010 with “Speak Now.” Her life in the spotlight — including her high-profile relationships and getting attacked by critics — provided lots of fodder for the album, which spawned a number of hits including “Mine” and “Back to December.” Although she lost best country album to Lady A, “Speak Now” earned Taylor two more Grammys: best country solo performance and best country song for “Mean.”
Two years later, Taylor Swift released her fourth studio album, “Red.” Once again, many of the songs on the album were about her romantic relationships, both good and bad. And once again, Taylor earned both critical praise and commercial success for the album, which featured tracks like “We Are Never Ever Getting Back Together” and “I Knew You Were Trouble.”
Although Taylor Swift had dallied around in the pop world, she had always predominantly been a country artist. All that changed in 2014 with her fifth studio album, “1989.”Taylor called the effort her “first documented, official pop album,” even dubbing it her favorite album to date. Fans and critics seem to agree: Not only did the album garner her the most sales worldwide, but in 2016, it earned Taylor her second Grammy for album of the year.
When Taylor Swift took home the Grammy for album of the year for “1989” in February 2016, she became the first woman to ever win the top award twice. While accepting the prize, she gave a gracious, inspirational speech: “I want to say to all the young women out there, there are going to be people along the way who are going to try to undercut your success or take credit for your accomplishments or your fame. But if you just focus on the work and you don’t let those people sidetrack you, someday, when you get where you’re going you’ll look around and you’ll know it was you and the people who love you who put you there and that will be the greatest feeling in the world. Thank you for this moment!” It was widely perceived as a mic-drop moment in her renewed feud with Kanye West, who’d claimed he was responsible for Taylor’s fame.
Taylor Swift’s “1989” tour was an event not to be missed — not only because fans could hear Tay’s hits like “Bad Blood,” “Shake It Off” and “Blank Space,” but because you never knew who else would be there. Night after night, celebs showed up en masse to be part of Taylor’s “squad” onstage. The more than 50 stars who strutted with Taylor included everyone from Justin Timberlake and Ellen DeGeneres to Mick Jagger and Julia Roberts, plus Taylor’s posse of supermodel BFFs as well as the U.S. Women’s World Cup Soccer Team.
In recent years, Taylor Swift has used her music business clout to take a stand against apps and websites that offer music streaming without paying artists. She began her quest in July 2014 in a Wall Street Journal op-ed. “It’s my opinion that music should not be free, and my prediction is that individual artists and their labels will someday decide what an album’s price point is,” she wrote. “I hope they don’t underestimate themselves or undervalue their art.” Then, later that year, she removed virtually all of her music from Spotify. The following year, she took on Apple Music by threatening to hold back “1989” from its streaming service because it wouldn’t be paying artists, writers or producers for plays during new members’ free three-month trial memberships. Although she can take the hit because she makes money touring, she argued that smaller artists cannot. The power play worked, as Apple changed its policy. More proof that Taylor and Apple have kissed and made up? In early 2016, she starred in a series of ads for Apple Music, which touted the three-month trial.
In May 2016, Taylor Swift was given one of the most fitting awards ever: BMI’s Taylor Swift Award. “I’m really super relieved that BMI decided to give me the Taylor Swift Award, because if they had chose somebody else to give the Taylor Swift Award to I’d be, like, kind of bummed about it,” she joked in her acceptance speech. What’s even more of an honor is that Taylor was only the second person to get an eponymous award from the organization, which represents and collects royalties for songwriters. (Michael Jackson was the first in 1990.) That same night, she won the award for pop songwriter of the year too.
Taylor Swift continued to rack up distinctions and honors left and right, even when they don’t come with statues made of gold that are given to her at fancy award shows. Naturally, she’s one of the most followed people on social media, including on Instagram and Twitter. Several of her videos have more than a billion YouTube views (yes, that’s billion with a B). She also has a number of Guinness World Records to her name, including most million-selling weeks on U.S. albums charts, most simultaneous U.S. Hot 100 hits by a female (though she’s since been bested), and fastest selling digital single.
Following a highly publicized split from Tom Hiddleston, Taylor Swift took a hiatus from Hollywood and social media starting at the end of the summer of 2016, with her only big appearance of the year happening in October at the Formula 1 U.S. Grand Prix in Austin, Texas. She didn’t get back on stage until February 2017, when she headed back to Texas for Super Bowl weekend in Houston to deliver a 90-minute set. The show was a memorable one complete with old tracks, brand-new tunes like “I Don’t Wanna Live Forever” (sans Zayn Malik), her first live performance of the song she penned for Little Big Town, “Better Man,” and even an acoustic version of another song she helped write, ex-Calvin Harris and Rihanna’s “This Is What You Came For.”
In May 2017, it was reported that Taylor Swift had quietly been recording a new album. The first single off “Reputation” — “Look What You Made Me Do” — was released in August and immediately started breaking records. Most notable? Its music video became the most viewed ever in a 24-hour period on YouTube, with more than 28 million views in a single day (it’s now been seen on her YouTube Vevo channel alone more than 1.2 billion times). “Reputation” was also the most pre-ordered musical item in Target’s history.
Taylor Swift launched her very own app in December 2017, “The Swift Life.” The app was designed to allow diehard Taylor fans to have a positive place to interact with each other and the star herself. It also grants them access to exclusive Taylor photos, videos, news and some pretty adorable Taymojis — emojis of Taylor and her two cats.
In March 2018, Taylor Swift’s “Reputation” album surpassed 2 million units in sales in America, making it the first album to hit that mark since Adele’s “25” did it in 2015. “Reputation” was also one of only two albums released in 2017 that sold a million copies in the United States. The other? “Divide” by Ed Sheeran, who, coincidentally, also appears on “Reputation” with good friend Taylor.
Taylor Swift is known for being a total cat person — so it wasn’t much of a shock when it was announced she’d be joining the cast of “Cats” — the film adaptation of Andrew Lloyd Webber’s iconic Broadway musical — in July 2018. (She plays flirty, glamorous feline Bombalurina in the 2019 movie, which tanked at the box office and with critics.) This marked the third major film Taylor’s been in, as she previously had roles in “Valentine’s Day” in 2010 and “The Giver” in 2014. She co-wrote the film’s signature song, “Beautiful Ghosts,” with Andrew and was rewarded with a few major award nominations for her efforts at the Golden Globes and the Grammys.
Taylor Swift, who previously held the record for the highest grossing U.S. tour by a woman thanks to the success of her 2015 “1989” concert trek, broke her own record with her 2018 “Reputation” stadium tour. According to Billboard Boxscore, in August 2018, Taylor surpassed herself as 27 of her U.S. dates grossed $191.1 million — and that was two months before her stadium tour run ended!
Taylor Swift has long refrained from voicing her political opinions, but she broke her own rule in early October 2018 when she took to Instagram to urge fans to vote in the midterm elections — and shared who she would and wouldn’t be casting a ballot for in her home state of Tennessee. “In the past I’ve been reluctant to publicly voice my political opinions, but due to several events in my life and in the world in the past two years, I feel very differently about that now,” she explained in part. “I always have and always will cast my vote based on which candidate will protect and fight for the human rights I believe we all deserve in this country.” The music star’s message was received loud and clear, inspiring a huge spike in voter registrations both nationally and in Tennessee. According to The Hollywood Reporter, in the 24 hours after Taylor’s post went up, Vote.org saw an uptick of 65,000 registrations — a number that grew to 240,000 48 hours later. For context, Buzzfeed News reported, nationwide, 190,178 new voters were registered in the entire month of September while 56,669 were registered in August. That’s power!
After Taylor Swift took home three trophies at the 2018 American Music Awards — for tour of the year, favorite pop/rock album (for “Reputation”) and best pop/rock female artist — she became the most decorated female artist in AMA history with 22 trophies overall. She surpassed the late Whitney Houston, who had 21 wins, and came within striking distance of the late Michael Jackson, who held the record for most AMAs wins ever with 24. Soon, she’d surpass the King of Pop…
Nov. 19, 2018, was a big day for Taylor Swift: First, Forbes named her the No. 2 top-earning woman in music between June 2017 and June 2018 thanks to an estimated haul of $80 million (just behind Katy Perry, who earned $83 million) — a figure that grew exponentially the following year thanks to the success of her “Reputation” world tour, the bulk of which took place after the timeframe closed. Later the same day, Taylor herself announced a landmark new record deal: She left Big Machine Label Group and signed with Universal Music Group’s Republic Records in a deal worth between $100M and $200M in guarantees, Forbes reported. But the truly remarkable part of the negotiations is that Taylor is keeping her future master recordings — and she secured a promise from the label that will benefit other artists too. “There was one condition that meant more to me than any other deal point. As part of my new contract with Universal Music Group, I asked that any sale of their Spotify shares result in a distribution of money to their artists, non-recoupable. They have generously agreed to this, at what they believe will be much better terms and paid out previously by other major labels,” she explained on Instagram. “I see this is a sign that we are headed toward positive change for creators — a goal I’m never going to stop trying to help achieve, in whatever ways I can.”
In November 2018, Taylor Swift set another record, besting previous title holders the Rolling Stones to become the artist with the highest grossing tour in U.S. history. Once the receipts were tallied for her 2018 concert trek, Billboard announced that the pop star’s “Reputation” stadium tour had earned $266.1 million on ticket sales of over 2 million across 38 dates. The Stones grossed $245 million from their “A Bigger Bang Tour,” which ran from 2005 to 2007, but it took them 70 shows to do it. Taylor, Billboard explained, “stole the title in just 38.”
Surprise! On April 26, 2019, following a mysterious 13-day countdown on social media, Taylor Swift dropped a new single called “ME!” plus a video for the track, both featuring Panic! at the Disco frontman Brendon Urie. Just one day later, she’d set a new YouTube record after racking up 65.2 million views: The pop star bested Ariana Grande’s “thank u, next” video to claim the honor of most watched video in 24 hours by a solo or female artist on the platform. Taylor also broke records on Vevo (for most video views in a single day) and Amazon (which confirmed that “ME!” had the most first-day streams as well as the most on-demand Alexa voice requests on Amazon Music ever).
On June 13, 2019, Taylor Swift announced that she would release her seventh studio album, “Lover,” on Aug. 23. Once again, she broke records: Apple Music reported that Taylor had set a new record (previously held by Ariana Grande’s “Thank U, Next”) for most worldwide pre-adds on its platform for a female artist ever (178,600 on the first day alone). “Lover” also became the most pre-added pop album ever, worldwide, on Apple Music. “Lover” also went to No. 1 and had the biggest sales week for any artist since the release of Taylor’s last effort, 2017’s “reputation.”
At midnight on June 14, 2019, Taylor Swift dropped the second single off her forthcoming “Lover” album, “You Need to Calm Down” — a pop anthem all about equality and understanding that made headlines for being her first track with an overtly political message. Three days later in the midst of LGBTQ Pride Month, Taylor released the track’s video, which featured a slew of celebrity friends (including Ellen DeGeneres, Adam Lambert, Ryan Reynolds, Ciara, the “Queer Eye” Fab Five, Laverne Cox, RuPaul, Todrick Hall and many more) and notably ended it with an on-screen call to action: “Let’s show our pride by demanding that, on a national level, our laws truly treat all our citizens equally. Please sign my petition for Senate support of the Equality Act on Change.org.” Months later in April 2020, she was honored with the GLAAD’s Vanguard Award, which is presented to allies who’ve made a significant difference in advocating for the rights of people in the LGBTQ+ community.
Taylor Swift sent the world another big message when she released her “You Need to Calm Down” video on June 17,making it clear that her years-long feud with Katy Perry — a beef that inspired Taylor’s song “Bad Blood” and Katy’s “Swish, Swish” track — was unequivocally over. Katy delivered a surprise cameo at the end of the video — she’s dressed as a cheeseburger while Taylor’s in a fries costume — and hugged it out with her onetime nemesis. Taylor later revealed on Britain’s “Capital Breakfast” radio show that the healing began in 2018 when Katy sent her a literal olive branch ahead of Taylor’s “Reputation” stadium tour. “We didn’t know if we were ever gonna really tell people about it. We wanted to make sure that was solid between us before we ever made the public aware,” she explained. The peace has lasted and they women decided the world should know about it. When Taylor contacted Katy about appearing in her video, Katy said yes. “She was like, ‘I would love for us to be a symbol of redemption and forgiveness.’ And I feel the same way about it,” Taylor told BBC Radio 1.
Taylor Swift’s “worst case scenario,” she wrote on Tumblr on June 30, 2019, came true when Scooter Braun’s Ithaca Holdings acquired the music artist’s former home, Big Machine Label Group, which was founded by Scott Borchetta, the same month. After news of the $300 million sale broke, Taylor — who claimed she was denied a fair and reasonable chance to buy back her own work despite having “pleaded” to — took to social media to slam the deal, which gave Scooter (who famously manages Justin Bieber and Ariana Grande and used to work with Taylor foe Kanye West) control of her back catalog. According to Taylor, Scooter has been part of “incessant, manipulative bullying” she’s experienced for years in part through some of his clients. “Essentially, my musical legacy is about to lie in the hands of someone who tried to dismantle it,” Taylor wrote. Scott hit back to deny some of Taylor’s allegations, Variety reported, and insisted, “Scooter has always been and will continue to be a supporter and honest custodian for Taylor and her music.” Celebrities quickly took sides, with Katy Perry, Halsey, Cara Delevingne, Iggy Azalea, Todrick Hall, Alessia Cara and more supporting Taylor in the wake of the drama. Scooter’s wife as well as clients Justin and new signee Demi Lovato took to social media to support the executive.
On July 10, 2019, Taylor Swift once again topped Forbes’ Celebrity 100 list after she earned an estimated $185 million in pre-tax income over the previous year — a figure Forbes classified as her biggest yearly earnings total to date. She did it thanks to the wild success of her 53-date “Reputation” stadium world tour, which pulled in a grand total of $345 million in 2018 and 2019, according to Forbes.
On July 23, 2019, Taylor Swift released the track “The Archer” from her forthcoming seventh studio album, “Lover.” The dreamy pop ballad earned critical acclaim and debuted at No. 69 on the Billboard Hot 100 — becoming Taylor’s 80th song to enter the chart. The same day “The Archer” hit airwaves, there was more good news: Taylor tied Ariana Grande for the most 2019 MTV Video Music Awards nominations — both women scored 10 — including for video and song of the year for her celebrity-filled “You Need to Calm Down” video.
Taylor Swift received a new prize — the first Teen Choice Icon Award ever handed out — at FOX’s Teen Choice Awards in Hermosa Beach, California, on Aug. 11, 2019. While accepting the inaugural trophy — which came in the form of a surfboard customized with images of her three cats — the pop star told fans, “These are my furry children, and this is a really proud moment for me that they are on a Teen Choice surfboard. Aesthetically speaking, this might be my favorite award.” She went on to offer sound advice to the teenagers in the audience: “One thing I wish I would have known when I was a teen is mistakes are inevitable,” she said. “You think you can possibly ace life, but it’s normal to make mistakes… it’s normal. That’s what’s going to happen in life.”
In August 2019, Taylor Swift finally released her much anticipated seventh studio album, “Lover.” It went on to become the bestselling album of the year by a solo artist after selling 3.2 million copies. That same month, she attended the MTV Video Music Awards, where she was up for 12 Moonman statues and took home three.
On Dec. 12, 2019, Taylor Swift was named Billboard’s woman of the decade at the Billboard Women In Music Awards at the Hollywood Palladium where she used her speech to criticize “toxic male privilege” in the music industry and celebrate fellow female artists. “Women in music are not allowed to coast,” she said in part. “We are held at a higher, sometimes impossible-feeling, standard.” Just a few weeks earlier, she was named artist of the decade at the 2019 American Music Awards where her wins for the night helped her shatter Michael Jackson’s record for all-time AMA wins. At the 2020 AMAs, she broke her own record when she added three more trophies to her haul: She now has a record-setting 32 American Music Awards!
In January 2020, Taylor Swift’s “Miss Americana” documentary was released in select theaters and on Netflix. It documented several years of her life and received critical acclaim. The film opened the 2020 Sundance Film Festival.
Despite a global pandemic, Taylor Swift remained hard at work in 2020. She dropped two albums within five months — both of which were total surprises. July’s “folklore” debuted atop the Billboard 200 chart, making it her seventh album to debut at No. 1. December’s “evermore” also debuted at No. 1, becoming Taylor’s eighth album to come out in the top spot. Both albums were critical darlings and big sellers: “folklore” finished 2020 as the year’s bestselling album in the States, according to MRC Data, which provides Billboard chart sales info. It marked the fifth time she’s had the top-selling album of the year.
In November 2020, Taylor Swift’s war with Scooter Braun and Big Machine Label Group took a new turn after Variety reported that Scooter had closed on a deal to sell Taylor’s masters to an investment fund, later identified as the Disney family’s Shamrock Holdings private equity firm, for “north of $300 million.” Taylor — who began re-recording her first six albums the same month — hit back after the news broke, tearing into Scooter and detailing how her team “attempted to enter into negotiations” but that they were foiled as his team “wanted me to sign an ironclad NDA stating I would never say another word about Scooter Braun unless it was positive, before we could even look at the financial records of BMLG (which is always the first step in a purchase of this nature.” She explained she would “have to sign a document that would silence me forever before I could even have a chance to bid on my own work. My legal team said that this is absolutely NOT normal, and they’ve never seen an NDA like this presented unless it was to silence an assault accuser by paying them off. … These master recordings were not for sale to me.” Read her lengthy statement in full here.
Later in November 2020, Taylor dropped “Folklore: The Long Pond Studio Sessions” on Disney+, a documentary in which she not only performs all 17 tracks from her acclaimed coronavirus lockdown album “folklore” but talks about the creative process behind the music with co-producers Aaron Dessner of The National and Jack Antonoff. In the film, she also confirmed widespread speculation that longtime love Joe Alwyn co-wrote two tracks with her using the pseudonym William Bowery. “There’s been a lot of discussion about William Bowery and his identity, because … it’s not a real person,” Taylor told Jack and Aaron in the movie. “So, William Bowery is Joe … as we know.”
Taylor Swift’s “folklore” album earned six nominations for the singer-songwriter at the 2021 Grammys and delivered one huge win: Taylor made history yet again as she became the first woman to win album of the year three times.
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