All 129 of Taylor Swift's Songs, Ranked

From teen country tracks to synth-pop anthems and rare covers, a comprehensive assessment of her one-of-a-kind songbook through 'Reputation' era

Load Previous

8. "Dear John" (2010)

A slow-burning, methodical, precise, savage dissection of a failed quasi-relationship, with no happy ending, no moral, no solution, not even a lesson learned – just a bad memory filed away. "Dear John" might sound like she's spontaneously pouring her heart out, but it takes one devious operator to make a song this intricate feel that way. ("You are an expert at sorry and keeping lines blurry and never impressed by me acing your tests" – she makes all that seem like one gulp of breath.) Every line stings, right down to the end when she switches from "I should have known" to "You should have known."

Best line: "I'm shining like fireworks over your sad empty town."

Back to Top