100 Greatest Bob Dylan Songs

From "Just Like a Woman" to "John Wesley Harding," we count down the American icon's key masterpieces

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61. "It Takes a Lot to Laugh, It Takes a Train to Cry" (1965)

This sexy shuffle was still a hopped-up blues called "Phantom Engineer" when Dylan debuted it at the 1965 Newport Folk Festival. Later, it was the first song he attempted during the sessions for Highway 61 Revisited – but Dylan, frustrated with the arrangement, set it aside after a few takes and cut "Tombstone Blues" instead. He spent his lunch break at the piano, working out a slower version that let him linger over the lyrics' blues tropes ("Don't the moon look good, Mama, shinin' through the trees") and sly asides ("I wanna be your lover, baby, I don't wanna be your boss"). The results felt both timeless and brand-new.

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