The album that got me started was Anthem of the Sun. That’s it for the Other One into New Potato Caboose and I was hooked. I wasn’t really into Jerry dirge-ballads at first (He’s Gone, Must have been the Roses, etc) although I got into it later on. I wanted to hear if this band could stretch. Boy could they ever!
So I guess how you would introduce someone to the Dead would depend on the type of music that person likes. The great thing about the Dead is that there’s something for everyone.
I’d get ‘em in through the out doors…pull the Old And In The Way version of “Wild Horses,” the Bob Weir/Rob Wasserman duet version of “Victim Or The Crime” (in the U.S. on the Michelob Sunday Night television program around 1989), "Knockin’ On Heaven’s Door" from The Pizza Tapes…and then on through the catalog proper starting with “Box Of Rain.”
If you’re pulling much live stuff, though, I would avoid Europe '72, since a lot of it was doctored in the studio before release…Merl Saunders actually plays the keyboard parts, for example, though he isn’t credited on the album…Jerry Garcia gave him one of the gold record awards for the album in thanks (from Keyboard Player magazine, IIRC).
You might also want to track down the Dead’s take on the Twilight Zone theme from the mid-80s for a few grins…
Don’t forget my fav.
STELLABLUE
Well, if you friend likes to catch a buzz, you could throw a space jam in there. Space>Fire on the Mountain from Dead Set got me hooked for good way back before I had seen a concert. Depends on whether the newbie would like the trippy stuff. I did, but that’s me and I suspect a whole lot of other fans.
I’d buy them ‘American Beauty’, but if only one, ‘box of rain’.
…into ‘Sugaree’.