Mine is "China Cat Sunflower/I Know You Rider" because it is my wife's fave and she introduced me to the Dead in a deeper way than "Truckin'" ever did. Okay it is two songs, but should always be played together imho.

I like this explanation for Slate!

""Terrapin Station": The turtle decals dancing across the bumper of your Volvo 740 wagon—she's still got some pep!—attest to your love of the divisive "Terrapin." For many Dead fans, the "Terrapin" cycle represents an overreach, a seven-part suite complete with a Homeric invocation ("Let my inspiration flow …"), a mysterious love triangle, and liberal use of a rain stick. Dead lyricist Robert Hunter claims he wrote the words and Jerry Garcia the music on the same lightning-lit night … but with neither knowing what the other was up to. "Yeah, right," say most. "Right on!" say you.

Yearbook quote: "The sullen wings of fortune beat like rain. You're back in Terrapin for good or ill again. For good or ill again."
Source(s):
http://www.slate.com/id/2217149/

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If I have to choose one song, it's "Friend of the Devil," mainly because I first heard it in college (it's one of the all-time great campfire songs), years before I first saw the Dead live.

http://vids.myspace.com/index.cfm?fuseaction=vids.individual&videoid=45005584

...and yeah, I know this is Garcia and Grisman and not the Grateful Dead, but the sound quality is a lot better than in the only Dead clip I could find.
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The Other One - great improvising AND it rocks.
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