Best Grateful Dead Songs: 20 Essential Consciousness-Expanding Tracks

19: Mississippi Half-Step Uptown Toodeloo (from ‘Wake Of The Flood’, 1973)

On the surface, this 1973 track is an easygoing demonstration of the Dead’s musical versatility – able to turn on a sixpence from the jugband-type verses to the simmering pre-chorus that gives the song its name. Still, this Jerry Garcia-Robert Hunter co-write has a keen sense of purpose and mortality, as Garcia explained when later discussing the lyric “I lost my boots in transit, babe/A pile of smoking leather”:

“I was in an automobile accident in 1960 with four other guys… 90-plus miles an hour on a back road. We hit these dividers and went flying, I guess. All I know is that I was sitting in the car and there was this… disturbance… and the next thing, I was in a field, far enough away from the car that I couldn’t see it.

“The car was crumpled like a cigarette pack… and inside it were my shoes. I’d been thrown completely out of my shoes and through the windshield. One guy did die in the group. It was like losing the golden boy, the one who had the most to offer. For me it was crushing, but I had the feeling that my life had been spared to do something, to either go whole hog or not at all…That was when my life began. Before that I had been living at less than capacity. That event was the slingshot for the rest of my life. It was my second chance, and I got serious.”

18: Dire Wolf (from ‘Workingman’s Dead’, 1970)

The Dead needed a fresh start at the beginning of 1970. On 31 January, their New Orleans hotel was raided, and the entire band was arrested on drug charges. Not only that, they needed a hit record to repay the time and money that had been lavished upon them by their label. Their problems sharpened their focus, and the band returned to their folk-blues past, recording the album that would change their fortunes forever, Workingman’s Dead, in a matter of days.

With it, their sound shifted to direct, accessible, harmony-strewn, acoustic-guitar-heavy Americana, as demonstrated by one of the first songs to emerge from the sessions, the breezy bluegrass swing of Dire Wolf. Again, the lyrics hinted at something altogether darker, with the narrator facing a mythical beast, as lyricist Robert hunter revealed: “The song Dire Wolf was inspired, at least in name, by watching The Hound Of The Baskervilles on TV with Garcia. We were speculating on what the ghostly hound might turn out to be, and somehow the idea that maybe it was a Dire Wolf came up. Maybe it was even suggested in the story, I don’t remember. We thought Dire Wolves were great big beasts. Extinct now, it turns out they were quite small and ran in packs. But the idea of a great big wolf named Dire was enough to trigger a lyric.”

17: Wharf Rat (from ‘Grateful Dead’, 1971)

A rolling, slow-burning epic featuring one of Jerry Garcia’s most impassioned live vocals, Wharf Rat, here recorded at Fillmore East in April 1971, and released on the album better known as “Skull And Roses”, was an early example of what would become a central theme in the best Grateful Dead songs: the underbelly of America, the outlaws, the people who have slipped through the cracks. The narrator of the song recalls a dockside encounter with a beggar who explains how he’s fallen on hard times, yet – as detailed in an extraordinary gear shift in the middle-eight – remains optimistic that the good times are around the corner. It’s a cautionary tale, made all the more effective by the suspicion that the narrator himself isn’t too far from going the way of the subject of the song.

16: Ramble On Rose (from ‘Europe ’72’, 1972)

Ramble On Rose – this version recorded at the band’s 26 May 1972 show at the Lyceum Theatre, London – is a great example of the Dead’s often-overlooked musical and lyrical wit. Hunter’s words provide a tour of folklore and pop culture, namechecking Crazy Otto (a US ragtime pianist), Wolfman Jack (the famed jive-talkin’ disc jockey) and Mary Shelley’s Frankenstein in the same verse. Meanwhile, the band take the song at an assured, sauntering pace, all the better to insert musical flourishes (some barroom piano here, a sting of blues guitar there) that embellish the lyric. And Ramble On Rose’s irresistible refrain helped make it a live favourite the band often returned to throughout their career.

15: Franklin’s Tower (from ‘Blues For Allah’, 1975)

Bursting through like a ray of sunshine after the mind-melting minor-key jams of Slipknot!,

the second track on Blues For Allah demonstrates the Dead’s mastery of dynamics. Jerry Garcia admitted that the jaunty groove of Franklin’s Tower was inspired by Lou Reed’s Walk On The Wild Side, specifically the section in Reed’s song where the female background vocalists sing “Doo, doo-doo, doo-doo-doo”. Garcia used that as a jumping off point for a snappy, organ-driven vehicle for an enigmatic Hunter lyric.

14: Playing In The Band (from ‘Grateful Dead’, 1971)

Written by guitarist Bob Weir and percussionist Mickey Hart, with lyrics from Robert Hunter, Playing In The Band became a totemic song for the Dead. Usually signalled onstage by Weir holding up ten fingers (to indicate the 10/4 time signature of the song’s intro), the lyrics glory in the faith the band have in their musical instinct (“Some folks trust to reason/Others trust to might/I don’t trust to nothing/But I know it come out right”). While this version is a relatively straightforward rocker, Playing In The Band’s live evolution assured its place among the best Grateful Dead songs, giving the group a cue to explore myriad musical tangents.

13: Box Of Rain (from ‘American Beauty’, 1970)

American Beauty saw the group further refine the sound of Workingman’s Dead, making their progression as a studio band keenly felt from the opening track. A co-write from bassist Phil Lesh and Robert Hunter, Box Of Rain would also mark Lesh’s first lead vocal. According to Hunter, “Phil Lesh wanted a song to sing to his dying father and had composed a piece complete with every vocal nuance but the words. If ever a lyric ‘wrote itself’, this did – as fast as the pen would pull.” The result is a work of rare beauty and reflection that resonates through the decades as one of the best Grateful Dead songs.

12: That’s It For The Other One (from ‘Anthem Of The Sun’, 1968)

An early indicator of Grateful Dead’s ambition, That’s It For The Other One was the near-eight minute, four-part suite that opened their second album, 1968’s Anthem Of The Sun. it became one of the group’s most-played songs, though not all of its parts – Cryptical Envelopment; Quadlibet For Tender Feet; The Faster We Go, The Rounder We Get; and We Leave The Castle – would remain intact as the song evolved over the years. Bob Weir’s The Faster We Go… section formed the basis of the band’s post-1971 jams on the song, his lyrics an early example of the Dead’s flair for self-mythology as he recounts the moment he hit the road as a youth.

11: St Stephen/The Eleven (from ‘Live/Dead’, 1969)

Garcia and Lesh rarely wrote together, but when their sensibilities melded – Garcia’s fluid, melodic guitar lines and Lesh’s flair for turning a song on its head with unexpected changes – the results were usually special. St Stephen first appeared on 1969’s Aoxomoxoa, but is best represented by the version released later that year on Live/Dead, where it formed part of a medley with the tricksy Lesh-Hunter tune The Eleven. This live version bristles with life: the joy of an utterly in-synch musical collective playing at full tilt.

10: Brokedown Palace (from ‘American Beauty’, 1970)

This serene, gospel-tinged meditation on death often proved the perfect set-closer for the Dead, bidding the audience farewell until the next time. Unbelievably, Hunter apparently wrote the lyrics on the same day as other contenders for placement among the best Grateful Dead songs, Ripple and To Lay Me Down, during a trip to London in 1970. It’s one of the Dead’s most graceful and beautiful moments, with a peaceful-sounding Garcia joined by the beatific backing vocals of his bandmates.

9: China Cat Sunflower/I Know You Rider (from ‘Europe ’72’, 1972)

Though China Cat Sunflower originally hailed from Aoxomoxoa, it’s best-loved in the form it would take from late 1969 onwards, when the band began segueing it into the traditional blues song I Know You Rider. The lyrics see Hunter at his most abstract and psychedelic, which only adds to the song’s appeal among Deadheads, as he reflected in Box Of Rain: “Nobody ever asked me the meaning of this song. People seem to know exactly what I’m talking about. It’s good that a few things in this world are clear to all of us.” The are few things that thrill Dead fans in quite the same way as when the tempo shifts up a gear and the band’s meandering journey to I Know You Rider begins.

8: Truckin’ (from ‘American Beauty’, 1970)

A song that recounts Dead folklore with a road-frazzled vocal from Bob Weir and the chunkiest of choogling backing from the band. The lyric came about after Robert Hunter spent more time on the road with the group, witnessing the chaos that surrounded them, as Weir told VH1 in 1997: “We left some smoking craters of some Holiday Inns, I’ll say that, and there are a lot of places that wouldn’t have us back. All of this is absolutely autobiographical, all the stuff in Truckin’.” The song became an intrinsic part of the group’s live set, not least for the release provided by the refrain “What a long, strange trip it’s been”, which became a motto of sorts as the best Grateful Dead songs continued to explore the outer reaches of music and the band’s own consciousnesses – a journey keenly followed by their fanbase.

7: Eyes Of The World (from ‘Wake Of The Flood’, 1973)

On record, Eyes Of The World was a samba-infused slice of blissed-out soul and a perfect reflection of Robert Hunter’s lyric: a Walt Whitman-esque celebration of compassion and empathy with nature. Its easy shuffle provided a springboard from which the band could launch into dizzying jams – just check out the 18-minute version from the Winterland 1974 show, included on the group’s 1999 box set, So Many Roads (1965-1995). Around the 11-and-a-half minute mark, the Dead appear to cease to be a mere rock band and become vessels for ecstatic communion. Eyes Of The World remained a mainstay of the group’s live sets, often as a transitional song following Estimated Prophet, and evolved into an entirely different beast from its studio incarnation.

6: Friend Of The Devil (from ‘American Beauty’, 1970)

Another of Garcia and Hunter’s outlaw songs, the narrator of Friend Of The Devil is on the run – from the law, from relationships – and unable to trust a soul. It’s set to a nimble acoustic backing which emphasises the captivating interplay between the band members. Still, were it not for the contribution of John Dawson of New Riders Of The Purple Sage, the song would have lacked its distinctive lyrical hook. According to a post in his online journal in February 2006, Hunter’s original chorus went: “Set out running but I take my time/It looks like water, but it tastes like wine.” When Dawson heard it, he suggested a crucial change: “We got to talking about the tune and John said the verses were nifty except for ‘It looks like water, but it tastes like wine’, which I had to admit fell flat. Suddenly Dawson’s eyes lit up and he crowed, ‘How about “A friend of the devil is a friend of mine.”’ Bingo, not only the right line, but a memorable title as well!”

5. Dark Star (from ‘Live/Dead’, 1969)

The beating heart of the Dead’s live set for many years, and never played the same way twice, the version of Dark Star from 1969’s Live/Dead emphasises what an enthralling aural happening a Grateful Dead gig could be. One of the most versatile entries among the best Grateful Dead songs, Dark Star can be spacey, dissonant, meditative or a total cacophony, depending on which recording you’re listening to. The version here – recorded at Filmore West, San Francisco, on 27 February 1969 – sees the group ebb and flow as one, from the yearning vocal passages to Garcia’s synapse-frying fretboard explorations. This is finely tuned alchemy; the band’s sense of each other’s musical sensibilities means they’re expert at giving each other space to take the music to vivid new places and then backing one another up as new themes emerge. As mesmerising today as it was over 50 years ago.

4: Uncle John’s Band (from ‘Workingman’s Dead’, 1970)

Another song that is almost a call to arms for the Dead, Uncle John’s Band is an outsider’s anthem – an idealistic ballad depicting a singer gathering a motley crew of outcasts and misfits together. Written just as the hippie dream was fading, Robert Hunter later said of the lyric: “It was my feeling about what the Dead was and could be. It was very much a song for us and about us, in the most hopeful sense.” As the first song on Workingman’s Dead it heralded a new direction for the band, but beneath the Americana exterior came a more unusual influence, emphasising Garcia’s musical curiosity, as he later explained: “At that time, I was listening to records of the Bulgarian Women’s Choir and also this Greek-Macedonian music, and on one of those records, there was this little turn of melody that was so lovely that I thought, Gee, if I could get this into a song it would be so great. So I stole it!”

3: Terrapin Part 1 (from ‘Terrapin Station’, 1977)

Taking up the entire second side of the Dead’s 1977 album, Terrapin Station, Terrapin Part 1 is a 16-and-a-half-minute suite comprising seven parts. One of the group’s most ambitious studio recordings, the song took shape while Robert Hunter was watching a lightning storm over San Francisco Bay from his home in San Pablo Bay. After sitting at his typewriter and writing the words “Terrapin station”, Hunter wrote the lyrics of the medley’s first part, Lady With A Fan, effectively as an appeal for inspiration. According to legend, Garcia was driving through that same storm, was hit by inspiration for an instrumental idea and rushed home to record it. When the two compared their material the following day, they found the pieces worked perfectly together. Though the studio version’s production is contentious among Deadheads, there’s no disguising the song’s ambition, power and strikingly evocative lyrics.

2: Bird Song (From ‘Reckoning’, 1981)

First released on Jerry Garcia’s highly recommended debut solo album, 1971’s Garcia, Bird Song soon became a de facto Dead number, a centrepiece of their shows and a highlight of the group’s 1981 acoustic live album, Reckoning. Though it wasn’t revealed publicly until Hunter published his 1990 lyric anthology, Box Of Rain, the song was an elegy to the tragic singer Janis Joplin, who had died on 4 October 1970. Joplin was one of the driving forces behind the San Francisco scene and had been close with the Dead, particularly keyboardist Pig Pen. Bird Song is a song of mourning and consolation that never becomes maudlin, its reflective lyric further ebbed by an insistent and winding central riff.

1: Ripple (from ‘American Beauty’, 1970)

A simple thing of generous, transcendent beauty, Ripple is a calming, zen-like meditation for the ages. Topping our list of the best Grateful Dead songs, it’s music to soothe the soul, with lyrics delivered by Garcia in his most peaceful croon. In the lyric “Let there be songs, to fill the air” Hunter managed to distil the Dead’s mission on this planet. Ripple doesn’t pretend to have all of the answers (“If I knew the way, I would take you home,” sings Garcia) but it creates a sense that we’re all in the same boat. That kinship with their fans is what ultimately makes the Dead so beloved: their finest songs create a feeling of community, of refuge for the misunderstood.

You’ve heard the best Grateful Dead songs, now find out why ‘American Beauty’ remains their finest hour on record.