The 10 Best Grateful Dead Songs

The 10 Best Grateful Dead Songs

To certain elitists, the name “Grateful Dead” represents an impasse; like the phrase “slap bass,” it is a combination of words whose very invocation can instantly elicit the gas face. It is not my intention to refute the negative connotations associated with the band — airheaded solipsism, boomer excesses, self-indulgent musical masturbation — nor do I intend this piece to double as acid test recruitment propaganda for disillusioned indie rockers (though, it should be said, some of them might benefit from a dosing). Rather, I’d like to introduce Dead-haters and Dead-neutrals alike to a most overlooked facet of the group’s music, one that separates them from every band of blunted jammers from Phish to Wooden Shjips: the songs.

Fanatical Deadheads, most of whom have heard almost every Dead song literally hundreds of times, frequently speak in terms of specific live versions of Grateful Dead songs rather than the songs themselves. When discussions of the Dead’s music are not dominated by references to mind-erasing jams, they’re rife with esoteric jargon and secret code words (“bass bombs,” “Betty boards,” “the Phil zone,” and, hey, what’s with all the “greater than” signs?); it can all be a bit difficult to penetrate. Even among Deadheads, the songs themselves are often taken for granted as mere launching pads for fearless improvisational jams. But forget everything you know about the band’s parking-lot flea-market subculture — the dancing bears, the tie-dye, and that one asshole at your high school with the blond dreadlocks — and you will be rewarded with some of most poetic and powerful tunes in the canon of American song.

Despite all appearances to the contrary, the Dead organization was shrewd about many things; there’s even a book titled Everything I Know About Business I Learned From The Grateful Dead. As with any major corporation (which the Dead became, officially, in 1976), mistakes were made, but on the whole, this was a decidedly savvy group of people. The Dead’s canniest decision of all, however, was not economic, but aesthetic: the decision to outsource lyric writing duties to people outside the band. Robert Hunter and John Barlow shared the Dead’s worldview and musical sensibilities but showed little to no interest in joining them onstage. Conversely, the members of the Grateful Dead loved to jam, but were largely limited as wordsmiths. And so, starting around 1968, the band would stick to the business of music, and let Barlow and Hunter worry about the words. Because of this unusual division of labor, it is crucial to include Hunter and Barlow in any discussion of the Dead’s greatest songs.

Hunter mostly wrote with Garcia; Barlow mostly wrote with Weir. There’s overlap, of course, and almost everyone who’s ever played in the Grateful Dead has at least a few writing credits (though, tellingly, very few appear on this list), but generally speaking the Dead’s oeuvre is defined by Hunter-Garcia compositions, Weir-Barlow compositions, and the various cover songs that actually comprise the majority of Grateful Dead music.

It is the dynamic of two very distinct songwriting teams that gives Grateful Dead songs their unique identity, even within the band’s catalog: Hunter’s lyrics are often preoccupied with phenomena, abstraction, and mythology, making him the perfect foil for the eternally curious and broad-minded Garcia; Barlow’s themes are more linear and elemental, vaguely cynical but not unromantic, characteristics that would seem to match the profile of his songwriting partner. It is telling that Hunter and Weir stopped collaborating around 1971 following a backstage feud over Weir’s ad-libbing on “Sugar Magnolia.”

Hear “Bertha,” “Sugaree,” or “Touch Of Grey” once and they’ll be popping into your head the rest of your life. The chorus of, say, “Ramble On Rose” is to a Deadhead what “The Rocky Road To Dublin” is to a denizen of an Irish pub, or what “99 Bottles Of Beer On The Wall” is to a car-confined child: obnoxious to the unconverted, sure, but sacred to the singer. These songs of outlaws, demons, and gamblers (lots of gambling in Grateful Dead songs!) have a way of getting into your blood; singing along with them just feels good.

Because the individual members of the Grateful Dead hail from vastly different musical backgrounds, there is no one clear, definable influence on the band’s sound, nor its songs; rather, the tunes reflect an omnivorous collective muse. Garcia-sung ballads like “Brokedown Palace,” “Stella Blue,” or “Attics Of My Life” owe debts to a folk tradition that predates Dylan, while albums like the psychedelic country Workingman’s Dead or the disco-leaning Shakedown Street showcase the sound of a band absorbing everything — the thick, polytonal atmosphere of electric Miles; the high lonesome apocrypha of Bill Monroe; the Bakersfield speedballs of Merle Haggard; the urbane boogie of the Band — and dealing it back out as mosaic. It’s not for nothing that many tales of Deadhead conversion (my own included) begin with an initial trickery, with some skeptical naysayer baited by the promise of psych folk, drone, fusion, or alt country only to find themselves balls deep into a sales pitch from the world’s most famous jam band. For fun, play the garage psych snob in your life the blistering “The Golden Road To Unlimited Devotion” and see if you can’t convince them they’re hearing a lost 13th Floor Elevators jam (just add amplified jug!).

I must emphasize that because we are discussing great songs in the traditional Western sense (which I will, for the sake of argument, define as songs that are as powerful performed on a lone ukulele as they are by a seven-piece band), much of the Grateful Dead’s greatest music will not be covered here. The studio recording of the band’s masterpiece “Dark Star,” for instance, is slight in comparison to live renditions, which could exceed 45 minutes — over eighteen times the length of the version found on the 1968 single. Similarly, fan favorites like “Scarlet Begonias > Fire On the Mountain” and “Playing In The Band” may have provided springboards for some of the Dead’s most magisterial improvised music, but no one is likely to bust them out around a bonfire. Indeed, a list of greatest Dead “jams” would look very different, and would include all of these.

Because of the band’s mutable relationship to their catalog, this list will necessarily focus less on specific performances and more on the lyrical and musical components of the songs themselves. However, I have included at the end of each entry some specific listening recommendations. Most of the recommended live versions can be streamed for free on the Internet Archive, while I’ve mostly relegated the ‘bootlegs’ in question to those easily procured via sanctioned sources like the Dick’s Picks series of soundboard recordings. Lastly, in brazen defiance of prevailing Deadhead wisdom, I have also endorsed several studio recordings. The list begins here.

10. “Touch Of Grey” (from In The Dark, 1987)

There exists a pejorative to describe Grateful Dead fans who gate-crashed their way onboard the bus after the band scored their first (and only) top ten hit in 1987: “Touchheads.” The contemptuous nickname is a reference to “Touch Of Grey,” the sweet and irresistible ode to survival that remains the Grateful Dead song almost everyone knows. Following the kind of FM radio attention that eluded the Dead for over two decades, MTV began showing at regular intervals the revolutionary music video for “Touch Of Grey,” directed by drummer Bill Kreutzmann’s son Justin. The Grateful Dead was suddenly very fashionable, but this unexpected success came at a price, as eager hordes of new fans threatened to disturb the fragile equilibrium of the Deadhead monoverse. Even the largest arenas suddenly found themselves unable to accommodate the front-runners, rubberneckers, and lookie-loos alongside the usual tribe of diehards. What had once been a moderately sized, self-sustaining enterprise was now a circus, and a Grateful Dead concert would never be the same. Though the unlikely success of the song may have proven more curse than boon, it was no fluke: “Touch Of Grey” is, quite simply, one of the Dead’s most infectious and magical pop songs, one that would have found its way to the charts whether it had been released in 1987, 1967, or 2007; it is the rare song that endures despite its ubiquity over supermarket PAs, in dentist’s office waiting rooms, and all points in between. The song’s stubbornly sanguine refrain: “I will get by… I will survive” would take on a new resonance in performances after Garcia’s rehabilitation following a diabetic coma in the summer of 1986.

Versions to hear:

In The Dark (1987)

07/13/84, Greek Theater, Berkeley, CA

12/31/85, Oakland Coliseum, Oakland, CA

9. “Estimated Prophet” (from Terrapin Station, 1977)

This odd Weir-Barlow piece in 7/4 time has long been a showcase for Garcia’s experiments with the Mu-Tron III auto wah effects pedal, a sound as synonymous with the Grateful Dead as Lesh’s bass bombs or Weir’s, um, creative slide guitar playing. As Garcia guides a pitter of short, clipped notes toward egoless, phantom spaces, Lesh’s slurring bass notes accent the tune’s sauntering halftime feel, stonily nodding toward reggae. “Estimated Prophet” concerns the sort of spiritual snake oil salesmen briefly ubiquitous in the late ’70s; self-styled shamans formed in the wreckage of the Love generation’s worst ideas. “The basis of it is this guy I see at nearly every backstage door,” Weir told David Gans in 1977. “There’s always some guy who’s taken a lot of dope and he’s really bug-eyed, and he’s having some kind of vision.” It was likely not lost on Weir that his own band commanded a similar sort of veneration, complete with devotees charting pilgrimages around the band’s movements around the country, and that the line between “fan” and “follower” was often easily blurred. Whether experienced as vision quest or bad trip, the ominous and riveting “Estimated Prophet” is a cautionary tale that portends dramatic consequences. It would also prove grimly prescient: Just over a year after the song’s February 1977 premier in San Bernardino, California, People’s Temple cult leader Jim Jones would successfully orchestrate a mass “revolutionary suicide” in Guyana, exterminating 909 people. File under: Darkside of the Dead.

Versions to hear:

Dick’s Picks Volume 3 – 5/22/77, The Sportatorium, Pembroke Pines, FL

Dick’s Picks Volume 15 – 9/3/77, Raceway Park, Englishtown, NJ

7/8/78, Red Rocks Ampitheatre, Morrison, CO

8. “Cassidy” (from Bob Weir – Ace, 1972)

Doubling as both an elegy to beatnik cowboy Neil Cassady and a salutation to Cassidy Law, the baby born to Dead sales manager Eileen Law and Dead roadie Rex Jackson, this Weir–Barlow composition is one of the Dead’s breeziest and merriest-sounding tunes. Though it was Hunter, not Barlow, whose writing style favored existential dualities, “Cassidy” casts an astute, uncharacteristically metaphysical eye on the circuitous nature of life and death. In an illuminating 1980 essay titled “Cassidy’s Tale,” Barlow, describing the elder Cassady as “The Avatar Of American Hipness,” claims that the connection between the poet’s demise and the birth of Law was “too difficult to ignore.” The version of “Cassidy” heard on Weir’s excellent solo album Ace (a Grateful Dead album in all but name) is strident and taut, bolstered by the harmony vocals of Donna Jean Godchaux; onstage, it would transform as many great Dead songs do. Though the Grateful Dead never officially recorded the song, “Cassidy” would become something of a fixture in Dead setlists for years to come, and holds the distinction, along with “Bird Song,” “Sugaree” and a few others, of being a rare “first set” song to frequently accommodate extended jamming.

Versions to hear:

Bob Weir – Ace (1972)

7/18/76, Orpheum Theatre, San Francisco, CA

5/7/77, Boston Garden, Boston, Massachusetts

Dick’s Picks Volume 13 – 5/6/81, Nassau Coliseum, Uniondale, NY

7. “Eyes Of The World” (from Wake Of The Flood, 1973)

“Eyes Of The World” is a song of riddles. The lyrics assert that we each superficially perceive the world somewhat objectively, but that our hearts are distinguished by their own individualistic homelands, seasons, and thoughts; eyes and heart exist as a perfect binary, with no one component less crucial or less reliable than its counterpart. The chorus of “Eyes Of The World” may seem, at first, grafted from another song, but this intrusion serves to enforce the dualism espoused in the lyrics. And though the message of civil harmony and shared accountability may seem deceptively simple, “Eyes Of The World” is dotted with what could be read as meta-commentary, like the lyric “Sometimes the songs that we sing are just songs of our own”; few lines better summarize the Grateful Dead métier of spontaneous creation and unwavering trust in the third eye. The sophisticated modalism of “Eyes Of The World” also distinguishes it as very much the product of a post-Europe 72 — that is to say post-Pigpen — Grateful Dead; it’s difficult to reconcile this jazzy, complex tune with the lascivious, bluesy rave-ups of the band’s early days. “Eyes Of The World” would usher in several years of “jazzy Dead,” which would soon give way to a full-blown “disco Dead” by 1978; the intersection of these two eras, taking place roughly between 1974 and 1977, would provide the breeding ground for the most exhilarating and intrepid music of the band’s career.

Versions to hear:

Live At The Cow Palace (2007)

6/18/74, Freedom Hall, Louisville, KY

Dick’s Picks Volume 3 – 5/22/77, The Sportatorium, Pembroke Pines, FL

6. “Ripple” (from American Beauty, 1970)

For those not already acquainted with the song, “Ripple” may require some suspension of irony. Light, jubilant, and superficially bearing some of the pseudo-mysticism that tends to date folk songs of this period, “Ripple” is definitely not for the cynical. Nevertheless, the song is a masterpiece. Its sage-like lyrics, upon closer inspection, suggest the perceptive eye of a poet, not a polymath (“Let it be known/ there is a fountain/ that was not made by the hands of man”), while David Grisman’s mandolin precisely corroborates the mysterious lyrics of the song’s chorus, its cascading strings forming a synergy with the song’s haiku refrain: “Ripple in still water/ when there is no pebble tossed/ no wind to blow.” It’s the sound of secular humanists wondering “what if?” Despite being relegated to the B-side of drug bust-themed single “Truckin,'” “Ripple” received considerable airplay, and though the Dead rarely performed it live (a mere 39 appearances between 1970 and 1988), it remains one the band’s most deservedly popular and well-loved songs.

Versions to hear:

American Beauty (1970)

Reckoning (1981)

10/31/80, Radio City Music Hall, New York, NY

5. “Althea” (from Go To Heaven, 1980)

This slack, laidback ode to a mythological Earth Mother is perhaps the funkiest song to ever reference Shakespeare. The frontline of Lesh, Garcia and Weir hack at a slinky, New Orleans boogie that recalls Tony Joe White or Little Feat, mutating into a single greasy organism; Lesh in particular pushes the subtly intricate pattern towards an exhilarating extrasolar groove, while new keyboardist Brent Mydland provides dabs of Fender Rhodes twinkle. Few bands have ever sounded so rubbery or so elegantly stoned (though parts of Palace Music’s 1995 album Viva Last Blues seem to channel some of the spirit). The song’s lyrics concern a world-weary narrator engaging in a dialogue with a goddess whose explicit wisdom he ultimately fails to heed. It is a song cautioning against distinctly moral problems: serial recidivism, shortsightedness, and spiritual emptiness, and taking Garcia’s well-publicized drug addiction into account, it is tempting to view “Althea” as Hunter’s coded attempt at an intervention for his friend. The Dead would try to recapture some of the song’s breezy chug seven years later on In The Dark soundalike “West LA Fadeway,” but the studio version of “Althea,” found on the underrated Go To Heaven album, captures the band at its swampiest.

Versions to hear:

Go To Heaven (1980)

Without A Net (1990)

Dick’s Picks Volume 6 – 10/14/83, Hartford Civic Center, Hartford, NY

4. “Friend Of The Devil” (from American Beauty, 1980)

Until around 1976, when it would be suddenly recast as a slow, narcotic ballad, “Friend Of The Devil” was a caffeinated Appalachian-sounding piece that retained, more than any other song from the classic American Beauty album, some of the country rock dalliances of Workingman’s Dead, released earlier that same year. Though written with assistance from John Dawson of New Riders Of The Purple Sage, the lyrics are vintage Hunter: a fugitive being pursued by “twenty hounds” for an unnamed crime eludes the law by employing the services of the Devil, whom he bribes. In between, there is cave-squatting, polygamy, and denials of paternity: all the ingredients for a classic Badlands ballad. “Friend Of The Devil” is, along with “Dire Wolf,” the Grateful Dead song that would have fit most comfortably on Harry Smith’s seminal Anthology Of American Folk Music. Hunter might agree: he told Relix that “Friend Of The Devil” was “the closest we’ve come to what may be a classic song.”

Versions to hear:

American Beauty (1970)

Dick’s Picks Volume 5 – 12/26/79 Okaland Auditorium Arena, Oakland, CA

Dick’s Picks Volume 8 – 5/2/70, Harpur College, Binghamton, NY

3. “Loser” (from Jerry Garcia – Garcia, 1972)

One of several Hunter-Garcia tunes written from the perspective of a no-count gambler, “Loser” is a note-perfect evocation of a deadbeat’s delusions of grandeur. The song’s protagonist repeatedly swears he’s “got no chance of losing this time”; one last score is all he needs, and then it’ll be the straight and narrow from here on out. It’s a tale as old as Mickey Spillane, Alfred Hitchcock, or Michael Corleone, but “Loser” is so vivid, so gorgeously rendered, you almost forget you know how this story ends. Depending on your tastes, Garcia ballads either drag or smolder, and “Loser” is as good a test as any to determine your side of that particular line. The song’s tempo is almost achingly slow, with rich, long stretches of deep-focus calm followed by tremorous bursts of manic energy. “Loser” is also the rare Grateful Dead song that seemed to improve with age, though not always for good reasons: like many of Garcia’s largo masterpieces, the song seemed to swim in direct proportion to Garcia’s worsening drug problem. Whether this is because Garcia began identifying with the song’s doomed narrator or was just nodding out in rhythm is, of course, purely speculative. Either way, this one’s a heartbreaker and a half.

Versions to hear:

Europe 72, Volume 2 (2011)

9/3/77, Raceway Park, Englishtown, NJ

5/2/80, Hampton Coliseum, Hampton, VA

2. “Uncle John’s Band” (from Workingman’s Dead, 1970)

1970’s Workingman’s Dead, perhaps even more than its immediate successor American Beauty, represents the absolute peak of Grateful Dead songwriting. Successive albums would each contain at least a handful of great songs, but Workingman’s Dead is literally full of them. Inspired by the formalist harmonies of Crosby Stills and Nash, the album’s rich vocalizing and lucid, capacious atmosphere represented a dramatic about-face from the sound of the band’s previous albums, which reveled in claustrophobia and chaos. “Uncle John’s Band” opens the album with a lilting, descending acoustic guitar riff and a close three-part harmony. Garcia credits Greek-Macedonian music for inspiring some of the more exultant-sounding licks, while Hunter’s annotation-worthy lyrics are embroidered with obscure references to old mountain tunes, Irving Berlin, and the Gadsden Flag of the American Revolution, among other things. Some have heard in “Uncle John’s Band” a sort of Grateful Dead theme song — with Garcia in the title role, of course — but both Hunter and Garcia have vehemently rejected this theory. Though lyrics like “He’s come to take his children home” do suggest a scattered hippie diaspora being led to glory by their virtuosic savior Captain Trips, these lines could just as easily apply to John The Baptist (and probably do). Complicating the matter further, Hunter has always claimed that the Uncle John of the song’s title was inspired by an obscure con man who traveled all over Kansas City with what he insisted was a musical — but microscopic — flea circus. Far out.

Versions to hear:

Workingman’s Dead (1970)

Dick’s Picks Volume 24 – 3/23/74, The Cow Palace, Daly City, CA

The Grateful Dead Movie Soundtrack (2005)

1. “St. Stephen” (from Aoxomoxoa, 1969)

A rare songwriting collaboration that added bassist Phil Lesh to the Hunter-Garcia songwriting team, “St. Stephen” is the Grateful Dead song most likely to convert even the most patchouli-averse rock fan. A lurching, psychedelic juggernaut, “St. Stephen” is loosely based around the story of the 1st century AD prophet of the same name, whose twin claims to fame are for appearing as the first martyr of the New Testament and for being stoned to death, and the song’s primal stomp is appropriately apocalyptic. I have thus far resisted trotting out the Deadhead axiom that the band’s studio recordings do not compare to their live analogues, but in the case of “St. Stephen,” there is no question about it: the wild, heavy version on 1969’s officially released Live Dead is the definitive and greatest extant version of the song — few bootlegs compare. Though the song regularly disappeared from the Grateful Dead setlist, sometimes for years at a time, the finest live renditions of “St. Stephen” reestablish the dynamic contract between audience and performer. Listen to the reaction from the rapturous Madison Square Garden crowd as the band begins to play the song’s unmistakable opening lick for the first time in almost five years; then listen to the band’s immediate musical response. Get goosebumps? Betcha did. Grateful Dead concerts were never exhibitions of prowess or commercials for the band’s latest product, but an open line communication between the band and its fans. It is for this reason, above all others, that the Grateful Dead remains so beloved nearly two decades after its final show. Just listen.

Versions to hear:

Live Dead (1969)

Dick’s Picks Volume 26 – 4/27/69, Labor Temple, Minneapolis, MN

10/11/83, Madison Square Garden, New York, NY

5/8/77 Barton Hall, Cornell University, Ithaca, NY

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