Taylor Swift vs. Hollywood: The Most Uncomfortable Encounters

Being Taylor Swift sounds like a dream, right? You have fans calling out your name, access to private jets, a pet named Olivia Benson, and the ability to sell out a stadium in less than five minutes, with scalpers reselling tickets for thousands of dollars. But even the world’s most famous women aren’t immune to awkward encounters, especially with inflated Hollywood egos.

Despite all the Grammys and fans’ undying love, Swift has had some majorly uncomfortable moments with fellow stars. Here are the most uncomfortable situations Taylor Swift has ever been in.

1. The Never-Ending Drama with Kanye and Kim Kardashian

If the 2009 VMA moment was awkward, what came next was a full-on feud. In 2016, Kanye dropped the song “Famous,” casually tossing in the lyric: “I feel like me and Taylor might still have sex. Why? I made that b*** famous.” You can only imagine that didn’t sit well with Tay-Tay.

Swift didn’t directly clap back at first, but her Grammy acceptance speech that year definitely sounded a bit sus. She basically pointed out that there will be people in your life who will try to undercut the success of others or take credit for their accomplishments.

Then Kim Kardashian jumped in to back up her man, claiming Taylor had approved the infamous lyric. Naturally, Taylor denied it, so Kim, after gauging the potentially insane drama levels in her head, released a video showing a phone call where Taylor called the line “a compliment.” But guess what wasn’t in the video? The part where Kanye called her “that b****.“

In a now-deleted post on Instagram, Taylor asked a very good question: “Where is the video of Kanye telling me he was going to call me ‘that b****’ in his song? It doesn’t exist because it never happened.” The situation escalated, leading to a confrontation between Swifties and Kim K fans.

2. The Kanye West Stage-Crash

While we’re on the subject of Kanye, we must talk about one of Taylor’s most awkward celebrity moments of 2009. At the MTV VMAs that year, Taylor won Best Female Video for her amazing performance of “You Belong With Me.” But as she was giving her acceptance speech, Kanye jumped onstage, hijacked the mic, and declared, “Yo, Taylor, I’m really happy for you, Imma let you finish, but Beyoncé had one of the best videos of all time.” Rude much?

Mic dropped, the crowd gasped, and a bewildered Taylor was left on stage mid-speech. It instantly became one of the most infamous award show moments ever. Kanye did apologize pretty quickly afterward, both on his blog and in a phone call but that didn’t change the fact that he acted like a jerk.

However, in 2015, at the same VMAs, someone thought it would be funny to have Taylor present Kanye with the Video Vanguard Award. On that day, she cheekily mirrored his words: “I’m really happy for you, and Imma let you finish, but Kanye West has had one of the greatest careers of all time!”

3. Ellen DeGeneres Turns Her Interview into a Dating Interrogation

Long before Ellen’s “nice” persona crumbled under workplace misconduct allegations, Taylor fans already felt the talk show host would happily cross some lines, especially during Swift’s 2013 appearance on The Ellen Show.

Right off the bat, Ellen wouldn’t stop asking about Taylor’s ex-boyfriends. First, she asked about 25 questions about Zac Efron, but clearly, that wasn’t enough. Ellen decided to do a lightning round with Swift by flashing pics of various men and telling Taylor to ring a bell every time one of her exes was on the screen. Taylor was clearly uncomfortable and even said this dirty trick made her feel bad. Eventually, she refused to play along, adding, “I don’t want to. They’ll send me angry emails, and I don’t want to get them.” Honestly, she should have rung the bell more to confuse everyone.

4. That Time T-Pain Accidentally Headbutted Her Chest

At the 2019 iHeartRadio Music Awards, T-Pain took the mic while hosting and shared a hilariously awkward confession: “Taylor, I never apologized to you. The first time we met—you’re so much taller than me, I thought you were standing on something. Without looking down, I tried to stand on whatever I thought you were on and—bam! Headbutted you right in the boob.”

He tried to play it off with an “I’m so sorry, that was not my intention.” But while the audience laughed, the camera cut to Taylor looking less than amused. Honestly, who wouldn’t be a little flustered getting surprise headbutted in the chest in public?

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