Top 10 Best Taylor Swift Fearless Era Performances

Top 10 Best Taylor Swift Fearless Era Performances

Welcome to MsMojo, and today, we’re counting down our picks for the most spectacular and breathtaking performances from one of Taylor’s earlier eras that we’ll love, “Forever & Always.” We’ll only be featuring renditions of songs that can be found on her “Fearless” album, unless a number from another era appears as part of a medley or mashup, then we’ll allow it. Sadly, we have to exclude eras tour performances due to lack of quality footage.

#10: “Fearless”
“Late Show with David Letterman” (1993-2015)

Remember those days when you were young and would dream about the perfect date with that special someone? Taylor Swift captures that feeling of nostalgic, youthful, and carefree love beautifully in her performance of “Fearless” on the late-night talk show. There are no theatrics, no dramatic lights, just Swift, her band, and her breathtaking vocals. Their remarkable harmony gives us the sensation of living inside a romantic movie montage rather than watching a rising star perform for an intimate late-night audience. If you were already familiar with T-Swift at this point, we imagine the splendor of the number came as no surprise. However, we have no doubt that she won over many new fans that evening.

#9: “White Horse”
“36th Annual American Music Awards” (2008)

What does it say about an artist when they can entrance audiences while spending most of their performance seated on a sofa, lit up by the soft glow of candlelight? As Swift sings this ballad of lost love, we’re totally enveloped by her emotion and heartache, almost as if we’re experiencing it alongside her. We’re practically leaning in, hooked onto her every word as she effortlessly entangles us with her gut-wrenching lyrics and immerses us in her story. That evening, she was awarded the AMA for Favorite Country Female Artist, showcasing her ability to connect with listeners through melodic tunes and relatable lyrics. Her talent for resonating with fans has only strengthened as her career continues to flourish.

#8: “Love Story”
“4th iHeartRadio Music Festival” (2014)

One thing we’ll always admire about Swift is her ability to change her music style and grow while still staying true to herself. That’s why it’s so exciting when she revisits timeless classics with a more mature voice, as she did at the 2014 “iHeartRadio Music Festival.” Swift still captures the innocent, rose-tinted fairytale she penned in her teen years, but by adding synths and changing the beat, she reintroduces the hit to a modern audience. We also can’t talk about this song’s reinvention without mentioning her magical “1989 World Tour” performance. We’ve cherished “Love Story” since its original release, but we’ve since also embarked on a whole new “Love Story” with these vibrant renditions.

#7: “You Belong with Me”
“Fearless Tour” (2009-10)

Taylor Swift’s skill for putting on a fantastic show has been a buzz-worthy topic for ages. Performances like this one are a blast to watch, showing why. Swift and her band take us back to high school in their uniforms, as do the dancers in cheerleader outfits, adding excitement with lively movements. It’s not just the fact that they’re channeling the music video that makes this special. Taylor’s ability to energetically navigate the stage while maintaining enough breath to hit every note is remarkable. Her dramatic costume reveal only amplifies the thrill, and she sends the crowd wild simply by striking a power pose as she soaks in the electrifying atmosphere. Her stage presence is boundless, and that high-energy finale almost leaves us whiplashed.

#6: “Forever & Always”
“43rd Annual Country Music Association Awards” (2009)

While we absolutely love Taylor’s extravagant performances, there’s something special that emerges when she relies on the power of her voice and the deep emotional connection to her lyrics. That’s the case here, where she brilliantly conveys the song’s raw emotions through flawless theatrical energy, powerful movements, and complete command of the stage. We imagine many a young Swiftie recreated this iconic performance while working through their own angst— although few probably dared throw any chairs. This captivating blend of emotion and showmanship showcases Swift’s versatility as a performer. So is it any surprise she’d already garnered such a dedicated fan base? That night, she also scored the CMA Entertainer of the Year award, incidentally becoming the youngest recipient yet.

#5: “You're Not Sorry”
“44th Academy of Country Music Awards” (2009)

After a magical introduction, Swift immerses us in the emotions of heartbreak, betrayal, and disappointment that permeate this song using just her voice, a piano, and her band. The simplicity of the staging, the dramatic lighting, and Swift’s powerful vocals blend seamlessly to make the audience deeply feel the narrator’s anguish. Performances like this highlight Taylor as a multifaceted performer who can connect with audiences on a range of emotional levels. “Fearless” is filled with beautiful tunes that capture a deep and relatable human experience, so we were hardly surprised when it won Album of the Year at the ACMs. We’re not sorry that we can revisit this performance whenever we need a musical shoulder to cry on.

#4: “Fifteen” feat. Miley Cyrus
“51st Annual Grammy Awards” (2009)

According to the singer, she always envisioned dueting this number with Miley Cyrus, and the opportunity came a-knockin’ when the time came for the Grammys. Neither was nominated that evening, but fans were treated to a memorable duet between these two youthful country powerhouses. Miley’s raspy vocals beautifully complement Taylor’s sweeter, softer sound; together, they sound divine. Despite the song being rooted in Swift’s personal experiences, you can tell that it stirs something deep within her singing partner, too. That’s the Taylor Swift charm; her songs and their stories are timeless and speak to a wide range of audiences. Can we dare to hope for more collaborations from this duo? If this performance is any indication, it would be pure magic.

#3: “Change”
“45th Academy of Country Music Awards” (2010)

Today, Swift is known for championing creative control and ownership, but her journey began long ago. “Change” marks one of her earliest calls for artistic empowerment. Singing from a stage surrounded by people, Swift enchants with heartfelt lyrics and vocals, effortlessly soaring to breathtaking heights — literally. But she eventually comes back down to earth and shows appreciation to her fans after a surprise costume change, of course. In every aspect of her performance, Swift embodies the power and beauty of song. Also, ending a set with crowd-surfing? Well, that’s just another example of how effortlessly cool she truly is, creating unforgettable moments that define the magic of live music.

#2: “Style”/ “Love Story”/ “You Belong with Me”
“Reputation Stadium Tour” (2018)

Taylor has an exceptional talent for ensuring her older tracks never go out of “style.” Even as her career and sound evolve, she retains the magic and charm that make her live performances irresistible. She’s a naturally gifted artist, effortlessly enchanting crowds with her stage presence and charisma. Here, audiences get to savor the nostalgia of “Love Story” and “You Belong with Me,” with Swift completely immersing herself in the medley while bringing her usual infectious joy and energy. It takes little more than her lively presence, impeccable vocals, and the backing of her band to make folks go wild. And can we talk about that seamless transition between the two “Fearless” tunes? Even when watching it online, we can’t help but jam along.

#1: “You Belong with Me”
“26th MTV Video Music Awards” (2009)

Performing at Radio City Music Hall is undeniably impressive, but it takes a truly unique performer to illuminate the New York subway and bustling streets with their talent. In her unforgettable 2009 VMA performance, Swift, a renowned visionary, leaves us all in awe by conquering the Big Apple in a remarkable fashion. After a gorgeous, subdued start, Swift kickstarts the party surrounded by adoring fans with her infectious charisma, affability, and, of course, this catchy tune. But she doesn’t stop there. She then brings the party to the streets, evoking “Fame” vibes as she sings from atop a taxi. This performance accentuates her vocal prowess, magnetic storytelling, and creative genius— in essence, everything that makes her a one-of-a-kind entertainer.

Which Taylor Swift live performance do you have a never-ending “Love Story” with? Go on, be fearless, and share it in the comments.