5. Let It Bleed (1969)

A first in a series of works — along with Neil Young’s Tonight’s The Night and Hunter Thompson’s Fear And Loathing in Las Vegas — that recognizes the counterculture-movement ’60s as more terrifying than idyllic. Songs like “Gimme Shelter” and “You Can’t Always Get What You Want” have been repurposed in a million sea-of-regret boomer contexts in pop culture through the years from Martin Scorsese to The Big Chill. But none of that really speaks to the unique sadness of Let It Bleed. The painful honesty of “Gimme Shelter”‘s “War, Children/ It’s just a shot away” refrain combined with the dull and disappointing realities of chasing unattainable dreams from the personal to the political to the visceral in “You Can’t Always Get What You Want” encompass the feelings of a band for whom the scales had fallen from their collected eyes. Other tracks like “Midnight Rambler” eerily and impossibly reflect the murderous acts of the Manson Family, which were happening almost simultaneously to the album’s release.