To make it easier on myself, I limited myself to one song per artist. This way, if I want to do an artist-specific top five list later, I won't have completely spoiled it.
5. "Folsom Prison Blues" (live) by Johnny Cash from At Folsom Prison (1968)
Originally recorded in 1956, the song took off when JR recorded it within the walls of Folsom, speeding up the original version and adding in the cheers of the inmates. Kicking off his legendary live album, "Folsom Prison Blues" is easily one of the coolest songs ever. It narrowly beat out Cash's "Ring of Fire" (1963) for a spot on this list.
Sample lyric: "But I shot a man in Reno, just to watch him die"
4. "Heroin" by The Velvet Underground from The Velvet Underground & Nico (1967)
I don't do drugs; I never have. Hell, I've never even been drunk. Yet, I'm drawn to this track every time I listen to it. For seven minutes and nine seconds, Lou Reed and company take us on a drug-fueled journey that starts off relaxed and mellow, then builds in tempo, only to calm and rise alternately, until the whole thing starts to come crashing down on the listener with Reed's desperation, the feedback from John Cale's shrieking viola, all accompanied by Moe Tucker's hypnotic bass drum that replicates the heartbeat of someone getting their fix. It might be the most hypnotic song I've ever heard. The ambiguity of its stance on the drug in question makes it that much better, with the song neither celebrating, nor condemning (or, alternatively, BOTH celebrating and condemning) it.
Sample lyric: "Then thank God that I'm as good as dead/
Then thank your God that I'm not aware/
And thank God that I just don't care"
3. "God Only Knows" by The Beach Boys from Pet Sounds (1966)
When you listen to this track, with its layered orchestra (including an organ, flute, baritone saxophone, french horn, viola, cello, accordion, violin, piano, electric bass, string bass, danelectro bass, clarinet, and percussion) creating a wave of sound, Carl Wilson's melodic voice, and the layered back-up vocals of Brian Wilson and Bruce Johnston, you realise that we kinda get ripped off by modern pop music. You just don't get pop songs like this on pro tools or Timbaland's studio. Of course, Brian Wilson kinda went crazy after making this record, so I guess there's a reason why most artists don't go to the depths needed to create this level of brilliance. Oh well, he created perhaps the most pleasant and rich love song ever, so it was worth spending a few years in his bedroom.
Sample lyric: "If you should ever leave me/
Though life would still go on believe me/
The world could show nothing to me/
So what good would living do me"
2. "Eleanor Rigby" by The Beatles from Revolver (1966)
Growing up, I didn't listen to rock, but of course I knew of The Beatles. I knew "Twist and Shout", "Yellow Submarine", "Hey Jude", the biggies. I readily accepted their "best band ever" label, but wasn't much interested in listening to them. Then I discovered "Eleanor Rigby", and was convinced: people weren't wrong about them. The haunting beauty of the string octet and Paul McCartney's gothic lyrics showed me that these weren't my father's Beatles, and gave me new appreciation of their entire catalogue.
Sample lyric: "Father McKenzie wiping the dirt from his hands as he walks from the grave/
No one was saved"
1. "Like a Rolling Stone" by Bob Dylan from Highway 61 Revisited (1965)
At six minutes and nine seconds long, an eternity for a single at the time (and pretty long for today too), Bob Dylan grabs your attention, and doesn't give a damn if you have things to do. You'll sit there and listen, dammit, and if you don't, then you'll miss what might be the best song in the history of the genre. Your choice. Just when you think he's building to the climax, he keeps coming back with more verses, with a sneer evident in the chorus and a big "fuck you" to everyone who gave him shit about going electric.
Sample lyric: "Once upon a time you dressed so fine/
You threw the bums a dime in your prime, didn't you?"
Honourable Mentions: "Georgia on my Mind" by Ray Charles, "The Sound of Silence" by Simon and Garfunkel, "All Along the Watchtower" by Jimi Hendrix, "What a Wonderful World" by Louis Armstrong