1 Playing in the Band

Standing on a tower, world at my command/ You just keep a-turning, while I'm playing in the band/ If a man among you, got no sin upon his hand/ Let him cast a stone at me for playing in the band."

It could be the Grateful Dead’s mission statement. With no burning desire for fame or fortune, the Dead were driven instead by a need to stand on a stage and play their music, irrespective of what anyone else thought. And at the heart of that process was this belief: "Some folks trust to reason, others trust to might/ I don't trust to nothing, but I know it come out right." It didn’t always work, of course, but the belief was constant and the off-road musical journeys were an essential part of any concert. Playing in the Band is a classic Dead game of risk: start an intricately-tooled song in 10/4, turn off halfway through down a road of unspecified length and content (different keys, time signatures or even different songs), then somehow coalesce back to the 10/4 song, several minutes, hours or even days later.

2 Ripple

Having defined the musicians’ function in Playing in the Band, here lyricist Robert Hunter defines the songwriter’s goal. Ripple may be admired for its Zen-like observations about life, but the introductory verses are the real meat of the song. "Don’t we all want a song to encapsulate our own thoughts in golden words delivered over sublime music?" he asks. Well, yes, but it’s more likely that you’ll get some "broken", "hand-me-down" thoughts like those in the rest of the song. But: "I don't know, don't really care/ Let there be songs to fill the air." Jerry Garcia gave Ripple the simplest of simple tunes and, at the end, the opportunity for everyone to sing their own song with their own words and meanings. I like to think the "ripple in still water" is analogous to the sound waves made by a song in silence.

3 Jack Straw

Ambiguous characters populate many a Hunter song: outlaws, oddballs and chancers fit nicely into the Grateful Dead family, itself comprising outlaws, oddballs and chancers. This tale of two buddies on the run from the law could be a film script, with its dramatic incidents and open landscape, but the climax of the tale is marvellously ambiguous: "Jack Straw from Wichita cut his buddy down/ And dug for him a shallow grave, and laid his body down." Maybe Jack’s companion was caught by the law and hanged, so Jack cut him down and gave him a decent burial. But I don’t think so. Bob Weir’s two-speed music reflects the duality of the song immaculately.

4 Looks Like Rain

They Love Each Other is, I think, the only positive love song in the Dead songbook. More common is the heartache song, of which this – one of the first Bob Weir songs with lyrics by John Perry Barlow – is a prime example. Built around the fear of being dumped ("You were gone, my heart was filled with dread"), it starts out as a country "crying song" featuring Garcia’s pedal steel and ends up as (almost!) a full-blown power ballad.

5 Black Peter

It has to be noted that death is a much more common theme than love in the Grateful Dead repertoire, whether in original compositions or cover versions. Here, poor Peter is on his deathbed awaiting the end, his friends around him. But are they there out of concern for him, from curiosity, or maybe just to chat about the weather? As so often in Hunter/Garcia songs, the bridge shows us the only truth we know for sure about the situation: "See here how everything led up to this day/ And it's just like any other day that's ever been/ Sun going up and then the sun going down/ Shine through my window and my friends they come around."

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6 Cumberland Blues

Black Peter is a typical Hunter character: poor, unremarkable, not particularly lucky. He’s the sort of man you’d find in an old country song working down the mine, complaining at the hours, moaning at his girl and dreaming of escape. In Cumberland Blues, Hunter tells of an actual Cumberland miner who wasn’t keen on the idea of the Dead playing what he thought was an old song from the area – although the gradual mood and musical changes mark it out from most country songs.

7 Estimated Prophet

The Deadheads were/are such an integral part of the band’s existence that they occasionally ended up in songs. This takes a doped-up west coast crazy from the stage door and lets him rave. Barlow gives him the language of Revelations and old spirituals, acknowledging the religious fervour sometimes found in the band’s following, who often quote lyrics as if they were divine wisdom: "My time coming any day, don't worry 'bout me, no/ It's gonna be just like they say, them voices tell me so." Weir’s music, again, is a delicious oddity: a reggae tune in 7/4 (Burning Spear sang it as straight reggae in common time).

8 Stella Blue

Ambiguity, love, loss, regret, the passage of time – this is one of Hunter’s most poignant and beautiful lyrics, set to one of Garcia’s most poignant and beautiful tunes. Even if it is about a model of old blues guitar, it’s still brimming with emotion and sad truth: "It all rolls into one/ And nothing comes for free/ There's nothing you can hold/ For very long." Stella is one of several sad, slow songs that the band used to flow into at the end of a second-set extended jam, just to calm everyone down and put everything into perspective after the chaos.

9 Victim or the Crime

This first collaboration between Weir and actor Gerrit Graham produced the band’s most controversial – yet by far the best – song of their late career. Possibly referring to Garcia and Weir themselves, it looks at drug and sex addiction. The uncomfortable nature of that reality, and its ongoing existence in the life of the band, is reflected in Weir’s angular music, based on a theme by Béla Bartók. It’s an ugly, dark, disturbing, yet glorious, piece that remains unresolved at the end, like the question in the title.

10 China Cat Sunflower

A song inspired by a trip to Neptune and the works of Edith Sitwell and Lewis Carroll, China Cat is pure psychedelic joy. And since that is the foundation on which the band grew up, it has to be in this list. It is attached – as it invariably was on stage – to the traditional song I Know You Rider, in which a condemned woman’s thoughts are aired. The juxtaposition of life and death, joy and sorrow, hope and despair, are typical of a Grateful Dead setlist and the musical transition between songs was a treasured feature of almost every concert.

• What do you think of Chris's choices? Let us know what he's missed and on Friday we'll publish an alternative playlist of your selections.