"Gates of Eden" (Bringing It All Back Home, 1965)
Generations of Dylan freaks have tried to crack this majestic acoustic masterpiece. Who's the "gray-flannel dwarf"? What "four-legged forest clouds"? All we know is we're in love with that motorcycle black madonna two-wheeled gypsy queen.
"The Ballad of Frankie Lee and Judas Priest" (John Wesley Harding, 1967)
Frankie Lee, the gambler, borrows money from Judas, who flees to a house called Eternity. That's where things get weird. Spoiler alert: Frankie dies! Or something!
"Changing of the Guards" (Street-Legal, 1978)
You have to hand it to Street Legal fans: They're a cult unto themselves. They never give up trying to figure this album out, not even when Dylan whips out Tarot cards. Best line: "They shaved her head/She was torn between Jupiter and Apollo."
"I'm Not There" (The Basement Tapes, 1967)
A melody this gorgeous makes you want to spend years pondering the song's bottomless mysteries. Dylan mumbles huge chunks in an antiquated dialect of his own devising ("Heaven knows that the answer/She's don't calling no one" ...?), but that just adds to the mood of total isolation.
"I'll Keep It With Mine" (The Bootleg Series Volumes 1-3, 1991)
Virtually everyone who attempts this ballad oversings it, trying to prove they have a clue what the chorus "If I can save you any time, come on, give it to me, I'll keep it with mine" means. But the only singer who's ever sounded like he gets the secret is Dylan himself — and he's not telling.