Top 13 Fearless Tour Moments!

Celebrate the 15th anniversary by revisiting Taylor Swift’s iconic Fearless Tour moments!

This Saturday, November 11th, is the 15th anniversary of Taylor Swift’s second album, Fearless. Of course, we now listen to her 2021 re-recording of Fearless (Taylor’s Version)! The Fearless Tour began in January 2009 and was Swift’s first headlining concert. She documents the tour in a three-part music documentary, Journey to Fearless. Swift gives us a behind-the-scenes look at her journey to stardom. At just 20 years old, Swift embarked on her first of many sold-out tours and gave us so many unforgettable moments.

1. Throwing a chair off the stage


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Taylor Swift brings all her leftover teenage rage and angst to her performance of “Forever and Always.” She starts the performance sitting in a red sofa chair opposite one of her dancers. When the song climaxes, Swift throws one of the sofa chairs off the stage in anger and rage. It truly is an iconic girl-boss moment.

2. “Teardrops On My Guitar” monologue

“And sometimes he would even talk to me… About his girlfriend. So, I never told this guy that I liked him. But I did write a song about him, so I think he knows now.”

Taylor Swift always thinks of fun ways to introduce her songs, and this one is definitely unforgettable. She plays into the innocent high school crush and strikes a chord with her fans, who can relate to having a crush on someone already in a relationship.

3. Fearless spins

During her song “Fearless,” Swift sings, “In the middle of the parking lot, yeah,” and does little spins when the guitar riff picks up. These “Fearless spins” became a staple in her performance of the song, and she still does them today on the Eras Tour.

4. Heart hands

During her song “Fearless,” Swift sings, “It’s the first kiss, it’s flawless, it’s really something… It’s fearless” and puts her hands over her head in a heart shape. The audiences at the Fearless Tour started giving hearts back, and it became a ritual of the fandom every time she sang the song. Fourteen years later, fans at the Eras Tour still send hearts back to her.

5. On-stage outfit change

The tour opened with Swift’s hit track “You Belong With Me.” She rose to the stage in a marching band outfit and performed half the song wearing it. That is until her dancers ripped it off, revealing her iconic silver sparkly dress. It was a flawless and jaw-dropping outfit change.

6. John Mayer

Well before Swift wrote “Dear John,” Mayer actually joined her onstage. During her show in Los Angeles, they performed Mayer’s song “Your Body is a Wonderland” and Swift’s song “White Horse.”

7. Faith Hill

Swift loves to surprise her fans by bringing special guests. During her Nashville show, Swift brought out one of her earliest mentors, Faith Hill. They performed Hill’s song “The Way You Love Me.” This performance showcased Swift’s country style.

8. Katy Perry

During another Los Angeles show, Swift surprised fans with Katy Perry. They sang Perry’s song “Hot n Cold” together.

9. Justin Bieber

It’s hard to believe that Justin Bieber was once one of Taylor Swift’s openers, but this was the case when the Fearless Tour traveled to England. His first show was at Wembley Stadium in London, where he broke his foot while singing “One Time.” His Wembley performance was cut short, as he could not perform the encore. However, he did join Swift again the following day in Manchester, where he was able to perform his entire set.

10. Mother’s Day tribute

“My mom’s sitting right there!”

At her Mother’s Day show in Moline, Swift surprises her mom by singing “The Best Day,” which she wrote for her. The song was not on the Fearless Tour setlist and was only played once on the tour in Evansville. Recently, Swift gave her mom the same surprise at her concert in Philadelphia during the Eras Tour.

11. Sparkly guitar

Swift debuted her iconic guitar during this tour. The bedazzled, sparkly guitar was used throughout the Fearless Tour and award show performances. She ended up remaking and bedazzling the guitar for the Eras Tour with her parents, which, of course, featured a rhinestone 13 on it.

12. Taylor walks into the crowd

During the show, she would walk through the crowd to a b-stage, bringing the show closer to those fans far from the main stage. She would hug fans, take pictures, and give them her bracelets. Swift would also appear in a random nosebleed section and perform a song from high up in the crowd. This was how she connected with her fans and the audiences at her shows.

13. “Should’ve Said No” in the rain

While “Should’ve Said No” is off Swift’s debut album, it earned itself a spot on this list. She closed the concert with this song as part of the encore section. She spent the last few moments of the song stomping and singing in the rain. The droplets pour down and magically spell “NO” as Swift walks underneath them and sings the iconic note change.

About the Author

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Jessica McCrorie

Jessica McCrorie is a junior at Chapman University’s Dodge College of Film and Media Arts, studying screenwriting and broadcast journalism. When she’s not writing for AfterBuzz TV or Heal Squad x Maria Menounos, she enjoys exploring her other creative outlets and interests, including filmmaking, reading romance novels, playing guitar, and listening to Taylor Swift.