For me, this set of years is entirely dominated by two artists: Bob Dylan and The Beatles. Of the 26 albums I own from this time, these two legends produced ten of them, and every single album in my top six (or so). The early sixties was a real turning point in pop music, as this time was sort of the second wave of rock and roll after Holly, Berry and Presley no longer were the dominant forces they had been in the previous decade.
Gold Medal: Rubber Soul by The Beatles
The Fab Four's first in their long string of masterpieces, Rubber Soul is extraordinary. I can imagine that tons of naysayers were forced to embrace the mop-tops after hearing songs like "In My Life" or "Norwegian Wood (This Bird Has Flown)"; this was undeniably mature stuff. It's clear that the Beatles spent substantially more time in the studio on this record than any of its predecessors and that the group's three songwriters were developing into uncommon talents, particularly John Lennon. There are enough classics here to drop the most skeptical of jaws. "Drive My Car", "If I Needed Someone", "I'm Looking Through You", "Girl" and, oh yeah, "Nowhere Man." This is the album that inspired Pet Sounds. And arguably, this is the album that turned popular music into an undisputed art form.
Silver Medal: Highway 61 Revisited by Bob Dylan
You don't have look very far to find a review calling this one of the most important records ever made. I'm particularly fond of Bruce Springsteen's quote about the opening track, "Like A Rolling Stone": "...on came that snare shot that sounded like somebody'd kicked open the door to your mind." After writing folk songs that inspired a generation of protesters, Bob decided to crank up the volume. After the half electric/half acoustic Bringing It All Back Home, Highway 61 was entirely plugged in, save the closer, "Desolation Row." This album is the product of a visionary poet on top of his game. It's abstract ("Tombstone Blues"), scary ("Ballad of a Thin Man"), goofy ("From a Buick 6", "), chillingly gorgeous ("Desolation Blues") and everything in-between. After the door to your mind is opened, you hear the ragged arrangements that suit Dylan's voice and attitude perfectly. And of course, like just about all Bob Dylan albums, the lyrics are too good to be real.
Bronze Medal: Help! by The Beatles
The third album was an incredibly tough choice but I ended up going with Help! as it continually fascinates me as much as any of records from the glorious catalogue of the Fabs. Sandwiched between the middling Beatles For Sale and the perfect Rubber Soul, Help! is like the awkward adolescent of the Beatles albums. It's not quite developed into brilliance but there is a whole lot of promise starting to show. Starting with the title track, the first original Beatles song to have nothing to do with romance or love, Help! is packed with great melodies and a new sort of melancholia never expressed by the band before. For example, "Yesterday", "Help!" and "You've Got to Hide Your Love Away" all reach a sort of poignancy far removed from the happy-go-lucky days of "Twist and Shout." The Beatles had always written or covered sad songs, but they never sounded quite like this. And it's clear to see John and Paul getting comfortable with their yin and yang songwriting voices, e.g. "Another Girl" (Paul's bouncy optimism) followed by "You're Gonna Lose That Girl" (John's acidic pessimism).