6. American Football, 'American Football' (1999)
If there is one thing that nobody ever tells you about young love, it's that your days are numbered from the start. Former Cap'n Jazz drummer Mike Kinsella learned this the hard way before graduating high school at 17, prompting one of the most devastating breakup albums in the history of breakup albums. Pulling lyrics straight from his old journal – including heart-stoppingly simple lines like "You can't miss what you forget" – Kinsella shares his teen confessions atop a tightly wound fusion of jazz and math rock. He and fellow guitarist Steve Holmes remain in constant dialogue through calculated trills and seamless repetitions, their tension interjected by the occasional trumpet and a Wurlitzer organ, which captures the magnitude better than Kinsella's words. Just as the prospect of college drove the star-crossed lovers apart, its conclusion would force the band to split as well – that is, until their reunion in 2014. S.E.