60 Songs That Explain the '90s cover image

Alanis Morissette—"You Oughta Know"

60 Songs That Explain the '90s

CHAPTER

Taylor Swift's Enduring Popularity

Dear John is my personal favorite in this genre because of the inside jokeiness. It's like an affecting song of a young girl being like, you broke my heart. But if you know that the song is about John Mayer, then number one, the title, Dear John, hilarious. And then the guitar solos that are so clearly mocking John Mayer within the context of the song. Oh, shit. The level of pettiness that only Taylor Swift can achieve.

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