The Dead are one of the few bands where I would recommend to start with the live recordings and not their studio albums.

They are one of my favorite bands. The Dicks Picks series are a great place to start, and there are plenty of free (and legal) places to download shows online. I started with the May 8th show at Cornell University. Many Dead fans, myself included, consider it their all time best. The second set, which includes Scarlet Begonias>Fire on the Mountain> Estimated Prophet is completely flawless.

I actually disagree with that, somewhat. While I will say that their live recordings are by far my favorite, I've noticed that even bands with a live focused sound are intimidating to those who are not familiar with the genre and work. A lot of people seem to have some weird block where "live recording" is synonymous with lame.

I've experienced more success introducing folks to bands with a stronger live presence by starting them out with the studio work most likely to tickle their fancy.

Wake of the flood is a great album by Greatful Dead. I love the part sung by Hunter specially.

Let Me Sing Your Blues Away, Here Comes Sunshine, Eyes of the World

I am somewhat with you on this, I started listening to Grateful Dead from their live recordings, but they can be quite overwhelming for the newer listener, so YES I would recommend starting with their studio albums.

Also: For newer listeners, start with the Dead Pod if you want to get into their live sets, they have A LOT of content! http://deadshow.blogspot.com/

The turning point album, they stopped playing rock after this one. I personally like their older stuff better.

Great album. One of my favorite Grateful Dead albums