1989

If there’s one thing Taylor Swift wants you to know about her, it is that she once felt deeply uncool.

Even as a superstar with best-selling albums, stadium tours, and high-profile friends, she said in 2014 that she had never felt “edgy, cool, or sexy.” Her first four albums hinge on that feeling, full of vivid, sprawling documents of failed romances that left her gasping for air, wondering how to be someone her lovers would miss. She was almost always the one who was in pain, the outsider, the underdog.

That changed with 1989. Its predecessor, Red, was the pinnacle of diaristic specificity, an album that blew up the tiny intimate details of her romances into public eulogies. The media surrounding that album critiqued Swift as clingy, boy-obsessed, and vindictive. 1989 is in part Swift’s response to the negative, often sexist, press she’d received. On the album, Swift loses her naïveté, dons a sense of unfazed nonchalance, and learns to navigate a world that underappreciated her lyricism and shamed her for dating too many men. She has said that she would work in marketing if she didn’t work in music but, really, she has already been doing both simultaneously and spectacularly.

— Pitchfork