Some random thoughts:
We think of the Dead as being reluctant to record in the studio, feeling that they were much better live....
The live experience rarely came out well in their releases, though - even though they put out so many live records through their career, I think their choices were often strange.
Live/Dead '69 is of course unassailable. They had recorded some '68 shows to use in Anthem of the Sun as a sonic experiment, which then took them months to combine & mix with the studio tracks. But it seems releasing a live-album didn't occur to them until they noticed how in-debt they were to the Warners label, thanks to all that studio time. A live record seemed the easiest way to record cheaply and make some money back to pay for Aoxomoxoa, and they had a long suite of music that was just right, as well as being totally different from their studio experiments.
So on Live/Dead they emphasized the longer jam pieces (most of which they'd been doing for a year), and mostly omitted the new Aoxomoxoa songs that were in their setlists. Garcia said, "We were after a certain sequence to the music. In the sense of it being a serious, long composition, it's our music at one of its really good moments." But Live/Dead was the last time they would fill an album with jams! So while it remains perhaps the finest introduction to the Dead for psychedelia-lovers, it may have also misled many people who thought the Dead would always be like this.... At that time, the Dead were evolving so quickly, Garcia said, "When Live/Dead came out, it was about a year out of date." (And that was only nine months after being recorded!)
Live/Dead was probably seen as an extravagant step at the time....I don't think by '69 there were a whole lot of live rock albums (let alone double-albums) that showed a whole different band than the studio records. Cream's Wheels of Fire comes to mind, there are probably others, but it was a new field - and the idea of releasing new songs only on live albums would be quite novel!
Once that was done, the Dead could have just stopped recording their shows - but they found it useful, or Bear insisted, so they started massing up piles of tapes.... From what I've read, they only checked these tapes right after the shows - after that, they never wanted to hear them again! They also didn't consider these tapes for release, apparently, but only for their own reference - when they wanted to record a live album, they brought in multitrack equipment. So it seems all their live albums were planned ahead, since they wouldn't be carrying around mulitrack decks on every tour.
Workingman's Dead & American Beauty in 1970 were their biggest hits yet, and Garcia/Hunter were on a creative roll....so you'd think they would follow up with more studio records. But, surprisingly, they decided not to do another studio album until 1973! (It's worth mentioning that the Sunflower records Vintage Dead and Historic Dead, from 1966 shows, came out at this time. They weren't strictly bootlegs, but apparently the Dead were horrified. Garcia said, "There's no point going back to the past....those performances weren't meant to stand around forever. They were for that night....it's not what's happening now. It's just a source of embarrassment." They were also not too pleased to see the fan-produced live bootlegs that started coming out in 1971 - in general they tried to prevent tapers from recording shows in the early '70s.)
The Skull & Roses album in 1971, Garcia particularly liked, feeling it showed the essence of the band - "It's the prototype Grateful Dead....a good example of what the Grateful Dead really is....people can see we're like a regular shoot-'em-up saloon band." I think it was meant as a snapshot, "here's where we are now", maybe for fans who were requesting another live album! It's not one of my favorites, but it does show where they were at in early '71, with all the covers and a couple new songs (with overdubs by Merl Saunders). They decided not to put on new versions of older songs, except for the Other One, which had certainly changed dramatically since 1967! Otherwise, fans hoping for a new Live/Dead were in for some cold water.
Again with Europe '72, the Dead decided to release their new songs in a live album rather than go to the studio. The Skull & Roses album was actually their biggest-selling record - and in fall '71 they'd broadcast a whole series of shows on the radio, so the droves of "Dead Freaks" clearly couldn't get enough - another live album probably seemed the natural thing to do. So they brought the multitrack equipment to Europe, hoping to record a live album that would help pay for the cost of bringing their entire organization on the two-month tour of Europe. (Hunter was disappointed that they didn't record his new songs in the studio, though.)
It must have been a surprise to get a whole triple album from the Dead, with a bunch of new songs (though the sides were pretty short). China Cat showed up for the second time on record, quite different from its Aoxomoxoa form - a couple 1970 songs were chosen, rocked-up since the originals - and jam-lovers got a lot to chew on with the third record. It's interesting, though, that with both these albums, the Dead felt the need to overdub in the studio. Listening to the original shows, it doesn't seem necessary! The production makes it sound like they're playing a super-slick set in an empty hall. In hindsight, it seems more surprising how much they left off Europe '72 (more Pigpen?), but it was still a pretty good release.
1973 is where the Dead started to fall off the rails with their live albums. After Pigpen died, they decided to put together kind of a tribute album to him. (And, finally finishing off their Warners contract was also an issue - they wanted their new studio recordings to come out on their own label.) So we got Bear's Choice - History of the Grateful Dead, vol 1. Bear's choice was interesting - he went back to the Fillmore East 1970 shows and put together an acoustic/blues/r&b record with a few Pigpen highlights, and only one song that had been on record before. A nice collection, but still feeling like a casual toss-off - it's their shortest live album (the only single-LP one), and it didn't represent those shows well at all. The Dead didn't much like it themselves, and were ready to forget it as soon as it came out - which might explain why there was never a vol. 2!
(I quoted Garcia's thoughts about it in another post here.)
After that came Steal Your Face....or 'Steal Your Money', as thrilled fans called it once they heard it. The Dead had managed to make very lousy recordings of their October '74 farewell shows - but after taking an extended touring break and recording Blues for Allah, they were short on material to release an album in 1976, and Garcia's work on the film was gobbling up money, so they decided to revisit these shows for another live album. (As Garcia said, "We were not working, and we didn't have anything else to deliver.")
They could have taken tapes of practically any '74 show and made a great album - but decided to stick with the film multitracks regardless of quality. Bear was very unhappy with the tapes and thought they were crap: "It was made from totally screwed-up master tapes... We spent months on it, almost overdubbing the entire multitrack tape in the studio. There was never any possibility to salvage any of it, and the movie was a total disaster as well as the album. The performances sucked, and no one could change that."
But Phil overrode him and picked out a double-album of songs that mostly hadn't been on albums before, covers and new songs - some of them things that had slipped through the cracks on the last couple live albums. Unfortunately, he also decided to leave out any of the jams that had made those shows notable! So this record of leftovers came out in '76 to massive disapproval - even Garcia admitted, "None of us liked it. I'm sure even Phil didn't like it."
Garcia also finally finished the Grateful Dead Movie, which had a more interesting selection and was a lot more satisfying. Of course, as the recent DVD showed, he still left out a mind-boggling amount of stuff, but the film was still over two hours, and he was very strict in picking things he thought looked good.
(In contrast to Steal Your Face, the 2004 5-cd '74 Movie Soundtrack is excellent - basically nonstop jams, though the sound is still kind of dismal. It's the kind of huge archival release that couldn't have been considered til recently, though.)
The Dead had also started a new never-ending yearly binge of touring - presumably they could have kept putting out a live album every year. But they'd decided that the studio routine was what they wanted for their new material - and as the years went by, new songs started drying up, and the albums kept getting worse.
They did record the Egypt '78 shows hoping to make a live album from that.....but the shows turned out to be too poor to use. As Garcia said, "What could be more amazing? A total eclipse, a full moon, the Great Pyramid. Everything perfect and we went and played shitty. It didn't really matter."
Finally in October 1980 they decided to record their acoustic/electric shows, and in a fit of generosity, released two double-albums. Garcia explained, "We really ended up with so much good material that it was a struggle. The idea of just one acoustic and one electric record was sort of pathetic, since our electric tunes are seldom less than eight minutes long. And that meant our fat electric album would have two songs on a side."
Reckoning was the acoustic release - as far as being a full document of the shows, it was perhaps their best live-album yet, including most of the acoustic songs they did. Dead Set was a selection from the electric shows....unfortunately, late 1980 was not a golden period for live Dead, although the shows were serviceable enough, and the songs further suffered from being edited (sometimes severely) for the record. By this time, their setlists were large enough that any selection would be somewhat random, but once again they aimed for songs rather than jams, and songs that hadn't been on previous live records - if this were an actual Dead set, most of it would be a first set!
Don Pearson, their sound engineer, was disappointed: "When the tape was rolling, they choked. Once they knew tape was rolling, they would do a mediocre show. [When] they did a fabulous show, of course the tape wasn't rolling."
Weir said of the album, "What we got were some nearly letter-perfect performances that were a little lacking in punch. But the old punch doesn't come across on tape... I think everybody had in the back of their mind that the tape was rolling and we were going for a record, and concentrated on a little neater rendition of a given tune rather than a more impassioned performance... Unfortunately, a number of the songs that we got that were really wonderful performances were also songs that had been out on so many records that we couldn't do it again. It would have been nice to put The Other One on, for instance....I thought Scarlet Begonias was going to be on there...."
After Dead Set, I think their live shows improved markedly in Nov/Dec '80. Considering how they could stretch out the jams in '79 and '81, it must have been a band decision to have such concise shows in '80 (for instance, Weir talked about cutting down on the spacey jams)....perhaps trying to reach new Go to Heaven fans?
The Dead didn't release anything for the next six years. Finally, impatient fans were treated to....Dylan & the Dead....which I will pass over in silence.
After painfully squeezing out a couple more studio albums in the late '80s, the Dead experienced a bit of a live renaissance in '89, and recorded shows from '89/90 for another triple-album. Phil again did the selections for this, but Without a Net turned out to be a good representation of where they were at. It's not my favorite period of the Dead, and I have many quarrels with the song selection, but at least it tries to represent the full range of a Dead show. It captured the first set/second set flow much better than Dead Set had - and although any setlist selection from 1990 would leave out much of their material even on 3 albums, the choices were at least interesting ones, and for the first time it wasn't governed by "let's avoid live versions we've released before" - two songs were even repeated from Dead Set!
Without a Net came out after Brent died - since the band entered a serious decline afterwards, it was pretty much the last gasp of new Dead releases. (Although there was a live Garcia Band double-album in '91.) Bob Bralove also produced the Infrared Roses record in '91 - but although this was taken from live shows, and the band must have thought it was pretty cool, I just don't consider an hour of manipulated midi space to be a live album.... There's also Grayfolded from '94, the John Oswald production of multiple Dark Stars that was apparently Phil's idea.
Overall, the Dead's live albums were a mixed bag. If you were a fan of their shows and wanted a record that was much like what you heard.....there was rarely a release you could turn to. Almost always, the Dead wanted their live albums to be a collection of songs, preferably new songs, and minimized the amount of jamming included.
Through the '70s I suspect the Dead really were looking for 'pop hits' as much as any band - hence all the work in the studio (especially '77-80), and the focus on just-right songs on their live albums. (Or check out how concise the songs on Wake of the Flood were, though they'd already been stretching them out live.) If true, they kind of lost control looking for that magic radio-friendly sound - they weren't being true to themselves - which helps explain why they skidded & stayed out of the studio for most of the '80s.
Anyway - the lack of jams on their live albums may just be due to the limitations of vinyl.... As Jerry said, if you put jammin' tunes on, you get only two tracks a side (as on E72) - or even just one a side (like Live/Dead)! Filling up an album with songs might have seemed to give better value to record-buyers. (But in this respect, fan-traded tapes worked much better than 'official' records, since tape sides are so much longer.)
It may also be that the Dead didn't trust their jams to hold up well, since they were pretty critical of their playing. The Dead didn't like listening to past work....they mainly heard the mistakes, and what they could do better now. As Garcia said, when he heard an old record, "I listen to what's wrong with it." So releasing a song, it doesn't change much, it's a good portrait - but a jam might sound 'dated' to them. Fans value a show as played - a snapshot of one moment - where the Dead were more about a process, and seem to have felt restrained in leaving behind too many snapshots of outdated moments. Garcia put it this way: "It's hard for me to go back to the past in terms of the music because for me it's a continuum and to stop it at one of those points....to me it always looks underdeveloped and not quite working."
Another possible explanation is the live-tape situation....the Dead were well aware from the '70s that fans were trading tapes. Artists always exaggerate the bootleg situation ("oh, why release that, everyone has it already") - and possibly, seeing a forest of microphones in front of them when they played, the Dead figured that just putting out a warts-&-all show would be irrelevant.
It is ironic about all the overdubs on the early '70s albums - to the extent the live performances just become 'backing tracks'. When the Dead released a live track, they wanted it to sound 'like a record', clean and professional - but I'd rather listen to any E72 show than that album... It is also ironic how the Dead stood at such a divide from their fans, who always wanted to hear "the real thing" rather than doctored-up compilations!
That changed in 1991, when One From the Vault came out. Finally, someone had heard the fans' prayers - they were going to release complete old shows! This plan didn't really get going until 1995....while the Dead were still active, there were only two Vault releases and two Dick's Picks. The release schedule exploded in '95, though, for obvious reasons.
The Dick's Picks series was actually even more of a breakthrough - the intent of the Vault releases was that, just like the regular live albums, they would be taken only from multitrack recordings of the highest quality. This creates evident limitations, ruling out most of the Dead's shows. But with the Dick's Picks, all those miles of 2-track reels could finally be used (with apologies for the quality printed on each cover)....as long as the Dead approved.
There were still some hitches to get through - Phil cast a harsh eye on some of Dick's picks, many were rejected, and he cut out a bass solo on vol. 1. (This may also have been due to a reel flip though - the other curse of Dead recordings. Many a show will never qualify for release because of a badly timed reel change.) Also, at the start they were only releasing 2-disc sets, which meant that shows like Hundred Year Hall had to be butchered for release. [Unfortunately we've returned to the 2-disc limit in recent years....]
I'll conclude with one reader's comment:
"It is ironic that a band that was known primarily for its live performances, who sought to try and capture the essence and "magic" of the live shows in their studio albums, mostly saw the live albums as Easy Money -- a way to fulfill contractual obligations, stop gap measures that would keep the overall operation afloat and allow them ultimately to get back into the studio!"