Wow, much more of a complicated question than it appears on the surface. (I am a fan who saw them several times, own several albums, a few downloads and have listened to many other shows; in other words, I'm nowhere near the expert Deadhead - not even intermediate! ;-) )

That disclosure now being made, I think I can help break it down. If you are going to go to your local Goody's or other new music store, you are going to be limited to the official releases. If you like the acoustic/bluegrassy music that they excelled at, buy the double set "Reckoning". If you like the more jam rocky, I like the double set "Without a Net".

If you are going to go to a store that carries more extensive (including used) inventory, you will likely be able to find some of "Dick's Picks". These are some band-released concerts that contain lots of concerts that are considered some of the best.

If you want to find some stuff online, go over to dead.net and check out episodes of the "GD Radio Hour" and "Taper's Section." They also have an extensive selection of concerts you can purchase. I haven't checked it out lately, but I think you could/can buy soundboard recordings of all their recent concerts. Rhapsody has an extensive catalog of concerts you can stream.

As far as choosing one of the many concerts, it really depends on what you like - the Dead continued to evolve - and are still evolving - throughout their 40+ years. I am partial to the early 70's, the early 80's, and the late 70's acoustic ("Reckoning").

Probably your best bet is to stream some of them first, and then pick one that you like. If you like specific songs, look for one with as many of them as possible.

Have fun, and let us know how the exploring goes!!!

The Grateful Dead were one of the most prolific touring acts ever, playing over 60,000 shows during 30 years. Even though they cut studio albums, true fans know the live albums had the real jams. The live album that best characterizes the psychedelic sixties sound is the Warner Brothers release "Live Dead" (1969) which includes their signature 25+ minute anthem Dark Star. The album was recorded by Owlsey "Bear" Stanley, a chemist and audiophile who helped them develop their early sound. For many fans the holy grail of live recordings are the 1971 Fillmore East shows, playing on my computer as I type. The Dead played an amazing five night run in April, captured on "Ladies and Gentlemen...the Grateful Dead" (2000). This amazing four CD box set has some of the most cherished live Grateful Dead moments captured on tape. The final CD has some simply amazing moments described as many fans being their finest ever with songs including Morning Dew, Alligator, Casey Jones, and We Bid You Goodnight. If you could have only one, this would be my suggestion!

Their greatest hits......that way you get all of the great songs.