Right guy, wrong combo platter, lady.

(see below for the Dylan choice from Courtney, I'll wait)

Bob Dylan wins this one hands down, and you got two of my three. I go in the other direction, though.

Bringin' It All Back Home is the rising. It's the beginning of the genius, and clearly, could be included in this discussion for the songs alone. I look at Dylan's career arc and I think that Back Home is a bit of a transitional-type record between protest-era Bob and Surrealist Bob. Either way, it's a fantastic piece of work, but I don't include it with my choice.

I go with the next three, two of which Courtney mentioned. Highway 61 Revisited, Blonde on Blonde, and John Wesley Harding. I think these three records truly encompass the ridiculous genius that was Bob Dylan in the 60's and provide a true three record arc that can be drawn out in a parabolic way. These three make up my Dylan identity, and I drift through them like walking in an art museum, just taking them in and wondering how in the world someone thought to create such beauty. He is the greatest songwriter of this modern era. There is no close second.

Others I considered:
Led Zeppelin: IV, Houses of the Holy, Physical Graffiti
Pink Floyd: Dark Side of the Moon, Wish You Were Here, Animals, The Wall (Animals fucks up that troika, sorry. Couldn't go there.)
Bruce Springsteen: The Wild, The Innocent and the E Street Shuffle, Born To Run, Darkness on the Edge of Town
U2: October, War, Unforgettable Fire
Yes: The Yes Album, Fragile, Close To The Edge
Judas Priest: British Steel, Screaming for Vengeance, Defenders of the Faith
David Bowie: Hunky Dory, Ziggy Stardust, Aladdin Sane
Peter, Paul and Mary: Peter, Paul and Mary, Moving, In The Wind

Those, and a bunch of others. This is a good, and fairly open topic. Feel free to play along in comments and let us know what you think. This is all in the eye of the beholder, that's for sure.

Enjoy your weekends.