Though a few of Paul and Art's albums technically fit this category of brevity, it's 1968's Bookends that has the overall edge. Their delicate songwriting is never more powerful than on "Old Friends," a tale of two elderly men reflecting on how much everything around them has changed and how uneasy it feels to simply live anymore. It's woeful and heartbreaking and yet gentle and reassuring. It's a dichotomy Simon and Garfunkel pulled off better than any of their peers, and Bookends showcases it brilliantly. Also... "America" and "Mrs. Robinson." Come on. A Little Taste: https://www.youtube.com/watch?v=Ul2hSba5pOs
