Any given day, we can only assume it must be great to be Taylor Swift. After all, she’s one of the richest and most famous people in the entire world. And both her wealth and celebrity status come from her immense talents as a singer. Whenever she wants, she can perform in sold-out stadium arenas all over the world…talk about an ego boost!
However, things haven’t always been as comfortable for Taylor Swift as you might think, especially when she runs into other celebs. The legendary singer has had one uncomfortable interaction with a celeb after another, so much so that she might need to “shake, shake, shake” off her bad luck streak.
Don’t believe that Tay Tay has bad luck with the celebs? Keep reading to discover her most cringeworthy encounters with the rich and the famous!
Kanye’s most infamous moment
Come on…you saw this one coming! It’s impossible to discuss Taylor Swift’s craziest celebrity interactions without mentioning her infamous encounter with Kanye West. At the 2009 MTA Video Music Awards, Swift’s song “You Belong With Me” earned her the award for best female video. But when she went to accept the award, everything went sideways.
Kanye West suddenly jumped onto the stage and grabbed a microphone. “Yo, Taylor, I’m really happy for you, I’ma let you finish,” he said. “But Beyoncé had one of the best videos of all time.” To this day, Kanye’s rude interruption lives in pop culture infamy. However, the two stars didn’t stay mad: Kanye almost immediately apologized on his blog and via a phone call.
Things came full circle at the 2015 VMAs, where Swift actually presented Kanye with his award for Video Vanguard. She didn’t waste time teasing him about the earlier outburst, though: “I’m really happy for you, and I’ma let you finish — but Kanye West has had one of the greatest careers of all time!”
Very public beef with both Kanye West and Kim Kardashian
Perhaps the most predictable thing about Kanye West is his unpredictability. Remember how he and Taylor Swift buried the hatchet and were all buddy-buddy in 2015? In 2016, Kanye released “Famous,” a song with a shocking lyric: “I feel like me and Taylor might still have sex/Why? I made that b**** famous.”
While Swift didn’t comment on this matter at first, her 2016 Grammy acceptance speech seemed pointed at Kanye. “There are going to be people along the way who will try to undercut your success or take credit for your accomplishments or your fame,” she said. Things got weirder when Kanye’s then-wife Kim Kardashian claimed Swift approved the lyrics; Swift denied the claim, causing Kardashian to release a video of Swift telling Kanye (who released a music video where he was in bed with a naked Swift statue) the lyrics were “like a compliment.”
In a now-deleted Instagram post, Swift absolutely went off on the other two celebs: “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,” she said. “You don’t get to control someone’s emotional response to being called ‘that b****’ in front of the entire world.”
Headbutted in the boob by T-Pain
By now, you’ve noticed that most of Taylor Swift’s cringe celeb encounters were uncomfortable emotionally rather than physically. However, at the 2019 iHeartRadio Music Awards, she had a celeb moment that was painful in every possible way. It all started when T-Pain was hosting the event, and he took the opportunity to apologize to Swift.
“Taylor, I never apologized to you,” he said. “The first time we met—you’re so much taller than me, that I thought you were standing on something.” Continuing, he said, “Without looking down, I tried to stand on whatever I thought you were standing on and — bam! Headbutted you right in the boob.”
He finished by saying, “I’m so sorry. That was not my intention.” The anecdote was meant to be amusing, but Swift looked downright mortified whenever the cameras cut to her reaction. And we can hardly blame her!
Getting bullied on air by Ellen DeGeneres
These days, most people know Ellen DeGeneres as a controversial figure…someone who retired from her TV hosting gig amid allegations of employee misconduct. Those allegations occurred relatively late in Ellen’s career, but Taylor Swift fans thought she was a bully way before that. In 2013, Swift appeared on the other woman’s show, where things got downright ugly.
Ellen practically integrated Swift on a singular subject: who the singer had and hadn’t dated. It began with repeated questions about Swift dating Zac Efron, and Ellen then began flashing photographs of different men while asking the singer to ring a bell if she saw a former boyfriend. Swift tried to appeal to Ellen’s humanity, asking, “Do you know how bad this makes me feel?”
Eventually, Swift demurred entirely, saying, “I don’t want to. They’ll send me angry emails, and I don’t want to get them.” Afterward, Ellen repeatedly rang the bell herself, bringing the world’s most awkward interview to an end.