The Most Embarrassing Moments of Taylor Swifts Career

Publish date: 2024-08-09

taylor swift

None of us are immune to embarrassing situations. It’s the time you come out of a restroom stall at a black-tie wedding in a beautiful tropical resort with your dress tucked in in the back, revealing Victoria’s Secret to everyone in the restroom. It’s the moment your kids open their mouths and totally out you when you’re least expecting it. It happens to everyone; no one is immune to the embarrassment that occasionally happens in life. We all suffer from embarrassing moments, even those of us that are not easily embarrassed. Even those people like Taylor Swift, the queen of the music industry. The girl who all mothers prefer their daughters look up to and the girl that all mothers wish their sons would marry. She’s a lovely young woman with an astounding career and talent that is just undeniable, but even Taylor Swift is not immune to life’s biggest embarrassments. Unfortunately for her, however, her embarrassments are usually documented and captured for the world to see, which, thankfully, is not a problem most of us have.

The Marilyn Monroe Moment

During one of her many performances, Swift made the mistake of standing just a little bit too close to a fan. No, not one of the people who love her endlessly. I’m talking about a real fan that blows air at people. She got just a little too close and the skirt of her purple dress went flying up. It exposed not just a sliver of her undergarments, but the entire thing. The entire world got to see T.Swift’s nude panties in all their very granny-panty style glory. Hey, we love someone who doesn’t feel the need to put on a thong with a dress, and we applaud Miss Swift for that.

The Grammy Mishap

There was a time during the Grammy’s back in early 2014 when the young singer thought that she won the Grammy for album of the year. The entire reaction was caught on camera and it wasn’t something that people found cute. In all honesty, I’ve watched the video several times and I don’t see anything wrong with it. It looks to me like she opens her mouth, claps her hands and is shocked. It looks like it could be shock that the other band won, but it doesn’t mean it was anything negative. Really, it doesn’t seem all that bad to me. However, the press and others in the world went entirely crazy about it, calling her rude and classless.

The Kanye West Moment

Anyone remember when Taylor Swift won an award at an award ceremony many years ago, and as she was about the issue her thank you speech, a very agitated Kanye West literally removed the microphone from her hands on stage and proceeded to tell her he’d give it right back. Then he turned to the audience and told them that the real winner here should have been Beyonce, and that she deserved the win over T. Swift. It turns out that he is a huge Beyonce fan, but not so much a huge Taylor Swift fan. And he made that quite clear that night. It was very embarrassing, probably both for Swift and most certainly for Beyonce.

At the end of the day, however, the person who should be the most embarrassed and the most ashamed of this is Kanye West. In fact, he actually left the country for a while after this incident and the backlash that was directed toward him. He might not think it’s fair considering he was standing up for what he believed in, which was the Beyonce should have won, but what he did was interrupt a teenage girl accepting her first VMA and giving a thank you speech so that he could tell everyone that the wrong young lady was on the stage. Thankfully, Beyone recognized the fact that this moment was ruined for Swift, and later invited her back to the stage to finish her speech. She told the crowd that she remembers her first VMA win when she was 17 and part of Destiny’s Child, and she remembers how excited and how on top of the world she felt, and she wanted to make sure that Swift’s moment wasn’t forever ruined. It really went on to prove that Beyonce is a class act. And the fact that Taylor Swift refused to say anything at all negative about the situation with Kanye proved that she, too, is a class act.

The Fall Heard Round the World

Fortunately for Taylor Swift, when she fell coming down the stairs during a performance on New Year’s 2015, it wasn’t the worst. Sure, it’s always a little bit embarrassing to fall down in front of someone, especially when it’s in front of millions of someones. However, she thankfully had already watched Jennifer Lawrence fall going up the stairs at the Oscars earlier in the year, so she was kind of good to go. It’s not something she probably wants to look back on with a fond thought, but it’s not going to come even remotely close to being the fall that people remember the most throughout the years. That will go to J.Law.

Her High School Cornrow Photos

When the press got a hold of photos of Swift when she was a high school student wearing her blonde hair in cornrows, she was a little embarrassed. She couldn’t believe that there was ever a time in her life when she was so silly she thought that the look was good for her. She even went so far as to tell the press that for a while, she was certain that she was going to make that her signature look. I’m going to tell you that I love it. I love the fact that this sweet, blonde country singer was looking to make cornrows her signature deal. It makes me giggle a little bit like a school girl. There’s just so many reasons to love Taylor Swift, and her honesty is just one of them.

Photo by Ethan Miller/Getty Images for iHeartMedia