Q:Rushmore: the Rolling Stones
I’m tempted to go with albums here, because the Stones are one of the few rockers that can stand up to that level of scrutiny, but to be fair to my own rules I’ll stick with songs.
“Ruby Tuesday” (1967) was the first Stones song I genuinely fell in love with, instead of appreciating for its historical importance. Something about how the barely suppressed sexual menace in the young Jagger’s voice is even more gripping when forced, almost strangled, into this quasi-medieval ballad form. (Honorable mention, same department: “Lady Jane.”)
“No Expectations” (1968) was for a long time my favorite Stones song, both because I loved lingering in Ry Cooder’s slide guitar and because the sentiment appealed to me: going away, probably forever, without regrets. I was pretty depressed, now that I think about it. (Honorable mention, same department: “Wild Horses.”)
“Rip This Joint” (1972) was my “song to represent Exile on Main St.” during a certain point in my music-listening life when trying to boil my favorite albums down to a single song was something I did. No, I don’t have any explanation for that. Exile is (probably) still my favorite Stones album (once upon a time it was Between the Buttons; I was really into the Kinks then), but its glory is its range. “Rip This Joint” still smokes, though. (Honorable mention, same department: “Tumbling Dice.”)
“Doo Doo Doo Doo Doo (Heartbreaker)” (1973) represents the point where I psychologically dug in my heels and refused to learn any more about the Stones; I still haven’t heard any of the full albums past Goats Head Soup (okay, I was suckered into buying A Bigger Bang, but I try not to think about that). It’s a fantastic place to forget them, though: lean, stringy, outraged funk that walks the edge between the social conscience of black funk and the sneering nihilism of NYC rock. (Honorable mention, same department: “Miss You.”)