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Ok, here goes...
The Grateful Dead - American Beauty
The pinnacle Dead album - an absolute must for any classic collection.
The Grateful Dead - Terrapin Station
Personal favorite, sort of a concept album - very chill.
The Rolling Stones - Exile on Main St.
Favorite Stones album - "Sweet Virginia" is a summer classic, "Loving Cup" and "Let it Loose" just seal the deal.
Bob Dylan - Blonde on Blonde
If I have to explain to you why you need to own this, you fail. 
Country Joe & the Fish - I feel like I'm fixin' to die.
Pure protest rock from teh sixties, but loads of fun and not all heavy handed and depressing. Country Joe is probably one of my favorite musicians from the 60's, just because in all I've read and seen from him, he seems like a chill guy - and that's definitely reflected in this release.
The MC5 - Motor City is Burning
Sound of the Chicago Riots. Just raw, nasty, rock music.
The Band - Music from Big Pink, The Band
"The Weight" is one of my all time favorite songs, and The Band is one of my all time favorite bands. "Music from Big Pink is great," but "The Band" has so many of the favorites on it - you've gotta get both.
The Talking Heads - Remain in Light
I should just tell you to buy all the Talking Heads albums, but if you need just one - this is the one to have. Easily their finest work. "Born Under Punches" is still one of my favorite tunes of all time.
Curtis Mayfield - Soundtrack from Superfly
Greatest funk/blaxploitation film soundtrack of all time. Mayfield is the fucking man, and any of us who've ever played a funky house track need to bow down and say thanks to him.
You also need to own any of the many compilations that Brewer & Shipley "One Toke Over the Line" appears on, at least one Tom Jones album, something from Blondie, "Electric Ladyland" (duh), everything from George Clinton and Bootsie Collins, and depending on whether or not you want to be a total fag, a Kiss album.

Hope that helps!
Edit: You don't like the Rolling Stones?!
I'm pissed I helped you now. Forget everything in my post, NOW!
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