Taylor Swift - Midnights

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Low-key imagine she's kicking herself for not doing it now. The narrative of world's biggest pop star performing at the same show her boyfriend might be about to win one of the biggest prizes in sport is something PR wet dreams are made of.
Ok but now imagine they aren't together in 2025 (hypothetically) and she opens the Superbowl with We Are Never Getting Back Together while he is in attendance? Taylor playing the long game for the real moment.

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She's #1 on the Billboard Power 100.
https://www.billboard.com/h/billboard-2024-power-100-list/

“The piece of advice I would give to the other executives on this list is that the best ideas are usually ones without industry precedent,” Swift tells Billboard. “The biggest crossroads moments of my career came down to sticking to my instincts when my ideas were looked at with skepticism. When someone says to me, ‘But that has never been done successfully before,’ it fires me up. We have to take strategic risks every day in this industry, but every once in a while, you have to really trust your gut and take a flying leap. My rerecordings are my favorite example of this, and I’m extremely grateful to my team and fans for taking that leap with me because it absolutely changed my life.”
 
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