1 "All Too Well"

Widely considered to be her magnum opus, "All Too Well" tells the cautionary tale of a romance gone terribly wrong. Listeners follow Swift and her lover (feverishly theorized to be Jake Gyllenhaal) as she paints a picture of domestic upstate bliss devastated by a breakup. The nearly six-minute track peaks halfway through, when Swift unravels and drops the line: "You call me up again just to break me like a promise / So casually cruel in the name of being honest." It's dramatic, hyper-specific, and gut-wrenching: Taylor at her finest.