Jerry Garcia’s 50 Greatest Songs

One of Garcia’s favorites, this darkly magical story-song was no easy creation. The song, Garcia said, “took about three years to write … maybe longer than that. I kept writing and writing versions of it. … Hunter would rewrite the lyrics. … I’d write a new melody. ‘No, that isn’t it.’ … It just went on forever.” But the work clearly paid off. The tale of a love triangle set in New Orleans, inspired by the film Black Orpheus, is brought to life by Garcia’s electric guitar, which was transformed via envelope filter to sound like a baroque horn. Lyrics about a mandolin melody as a lover’s voice may be the best metaphor ever for Garcia’s art.

Another Hunter lyric with roots in some mythological Old West and a ramblin’, gamblin’ man who only wants “10 gold dollars,” “Loser” was first played onstage with the Dead before Garcia cut it himself for his first solo album. Unlike the jaunty melodies that often accompanied such lyrics, “Loser” is shot through with desperation and gloom, and Garcia’s version — on which he played all the instruments, accompanied only by Dead drummer Bill Kreutzmann — digs deep vocally and musically.

By the early Eighties, Garcia was grappling with his escalating and ultimately life-threatening drug addiction, as well as malaise within the Dead itself. Perhaps some of his feelings spilled out on the title track (and high point) of his 1982 solo album. It was one of those moments when Hunter’s lyrics perfectly reflected Garcia’s situation: “Reach for the sun, catch hold of the moon/They’re both too heavy, but what can you do?” he sang. But the track itself — recorded at the Dead’s own Club Front studio and featuring Ron Tutt, drummer for Elvis and the Garcia Band — has a beatific glow: the sound of Garcia fighting off the blues, one song at a time.

Garcia had one reservation about this gently rocking track, co-written with Hunter for the band’s first self-released album. “He took objection to the word ‘Styrofoam,’ ” Hunter recalls. “He said, ‘This is so uncharacteristic of your work, to put something as time-dated as the word “Styrofoam” into it.’ ” That minor qualm didn’t discourage Garcia musically, though. Trading jaunty licks with fiddle player Vassar Clements, he delivered a wry, buoyant performance that achieves the timelessness he was looking for.

These two linked pieces, from one of the Dead’s most adventurous studio albums, are testaments to Garcia’s melodic ingenuity. Originally an instrumental, “Help on the Way” melded jazz-rooted chords with funky leads and lyrics that hinted at Garcia’s tumultuous personal life (“I was blind all the time I was learning to see”). Credited to the whole band, “Slipknot!” featured Garcia’s atonal licks. No wonder that the avant-leaning Lesh called the songs “one of our finest exploratory vehicles.”

Garcia and the Dead were always extremely critical of their recorded output; they always felt more comfortable onstage, where songs truly blossomed, than in a studio. In that regard, Garcia was never more unhappy with a studio performance than he was with this country-blues breakup song. “The song that I think failed on that record was ‘High Time,’” Garcia told Rolling Stone in a 1972 interview. “It’s a beautiful song, but I was just not able to sing it worth a shit.” Others would disagree. It’s a classic example of the band bending traditional music to fit its own ideals. The elliptical way Garcia ends Hunter’s verses with “Well, I know” is arrestingly pretty, and, living up to the title of the song, Garcia’s delicious pedal steel work was way spacier than anything Merle Haggard or Buck Owens — his California country heroes — would have condoned. The song also has a special, strange place in Dead history: It was part of their five-song set at Woodstock, a year before “High Time” was recorded. Garcia always put down that performance, too.

One of the last and most poignant songs Garcia and Hunter wrote together was this steadfastly contemplative ballad, which gradually built in tension over its 11 minutes. As Hunter told Rolling Stone in 2015, “Both of us were very interested in where we could go with that kind of strange and irregular construction. I almost feel in certain respects we were just getting started. We were past one whole phase of writing, and ‘Days Between’ signaled the next.” Lines like “The singing man is at his song/The holy on their knees/The reckless are out wrecking/The timid plea their pleas” hinted at the Dead’s own story, which Hunter confirmed: “That is the story of what went down as far as I can see. More so than any other single song. It seemed to get my feeling about those times and our place in it.” The Dead played it live in the Nineties but never finished a proper studio recording of it. 

Black Pete is a traditional Dutch bogeyman, but Hunter turned him into an ailing, sympathetic figure — and Garcia merrily took on the role. Over a languid, lazy-afternoon rhythm, Garcia delivered world-weary lines like, “See here how everything/Lead up to this day/And it’s just like any other day.” According to Hunter, the song began as a “jumpy little tune” before Garcia “made a monster of it.” That was emblematic of Garcia’s approach — he said that during their Americana phase, the Dead wanted to be a “good old band,” but as “Black Peter” shows, they could never settle for clichés.

One of Garcia’s loveliest recorded vocals came, ironically enough, on this veiled assessment of the tortured state of the Dead in the mid-Seventies. Since “Ship of Fools” was written at the height of Watergate, it was also possible to hear its allusion to a hapless ship’s captain (“strangest I could find”) and a foundering vessel as a metaphor for America itself at the time. The song, debuted onstage shortly before it was recorded, was also early proof of Garcia’s love of slow, mournful melodies, which were enhanced in the studio by the abstract honky-tonk piano of new member Keith Godchaux.

Like so many of the songs on the Dead’s third album, Aoxomoxoa, this delicate Fairport Convention-style ballad is a studio confection rather than one for the road. (Although they played it in their bizarre 1969 TV appearance with Hugh Hefner on Playboy After Dark.) “Mountains of the Moon” is more English than American in its folk roots, with a medieval-themed lyric and Tom Constanten’s lilting harpsichord. “That song turned out nicely,” Garcia recalled. “I don’t know what made me think I could do a song like that, but something at the time made me think I could do it.”

Garcia was less than thrilled when Hunter burst into the kitchen of the house they were sharing with two new songs, “Deal” and “Loser.” “He was reading the paper…and wasn’t at all pleased to be confronted with work, emitting a trademark ‘aaargh’ of displeasure,” Hunter recalled. But soon enough, Garcia had written a melody to accompany Hunter’s narrative of a boastful card player. The song started as a shuffle when the Dead began playing it live in early 1971, but Garcia toughened it up for his first solo album, with a slide-guitar riff and a rarely heard growl in his vocal.

“I had a cat sitting on my belly and was in a rather hypersensitive state,” Hunter said, describing the inspiration for this whimsical song. “This cat took me in all these cat places.” Recording it for Aoxomoxoa, the Dead indulged in the possibilities of new 16-track tape machines. “We put too much on everything,” recalled Garcia. “A lot of the music was lost in the mix.” Still, the relaxed groove, twinkling guitar lines and skipping melody were a perfect counterpart to Hunter’s free-associating lyrics. Often paired with “I Know You Rider,” it became one of their most-frequently performed songs.

Hunter penned lyrics for this seminal Grateful Dead song in Barcelona, Spain: “Topped up on vino tinto, I composed it aloud to the sound of a jew’s-harp twanged between echoing building faces by someone strolling half a block ahead of me in the late-summer twilight.” Starting with the ambling-along-the-road twang of Garcia’s guitar, the Dead took Hunter’s tale — a loser bumpkin who’s a little slow to realize it’s time to give up and head back to his home state — and brought it back to American roots music. Garcia felt the song tapped into the tough-edged Bakersfield sound embodied by country acts like Buck Owens and Merle Haggard: “It’s a cop from that world, although not consciously, and it’s not from any specific tune. Just the feel.” Debuted at a Minneapolis show in 1971 and released on the live album Europe ’72, “Tennessee Jed” showcased the sparkling interplay between Garcia and pianist Keith Godchaux, as well as Garcia’s falsetto, which is on display during the chorus. Though never recorded in a studio, it was performed live more than 400 times.

Hunter originally titled this ballad “The Suicide Song” following a friend’s attempt at taking his own life. But even after it was renamed “China Doll,” Garcia still felt haunted. Accompanied by a harpsichord, Garcia’s guitar creeps in just behind the beat, and he sings as if he’s sighing from another realm. The result is one of his most gripping vocal performances. As Hunter said, “The song is eerie and very, very beautiful the way Jerry handles it.” A later, live acoustic version on Reckoning showed how Garcia could enhance the dark power of “China Doll” by stripping it down even further.

Hunter wrote this country death ballad (a fine showcase for Garcia’s pedal-lsteel playing) after watching the Sherlock Holmes movie The Hound of the Baskervilles on TV. For Garcia, the lyrics — especially the “please don’t murder me” refrain — took on a contemporary meaning. “The Zodiac killer was out murdering in San Francisco,” Garcia said. “Every night I was coming home from the studio and I’d stop at an intersection, and if a car pulled up, I was like, ‘This is it, I’m gonna die now.’” When Garcia received a death threat at one of the Dead’s last shows, they pointedly played “Dire Wolf.”

“I always thought it’s a pretty good musical picture of what cocaine is like,” Garcia once said of one of the band’s most beloved songs. “A little bit evil and hard-edged and also that sing-songy thing.” First worked up in 1969, “Casey Jones” attracted immediate attention for Hunter’s lyrics — a druggy twist on the true story of train conductor John “Cayce” Luther Jones, who died in a crash after he missed a signal. For extra effect, the song starts with the sound of someone snorting up, although Hunter worried about the “lightly romanticized context” of the lyrics.

By the beginning of the Eighties, Garcia and Hunter weren’t writing together as much as they once had, but when they did collaborate, they could still summon up the old magic. The slow, lovely “Althea” stands out on 1980’s lackluster Go to Heaven; a shuffle that proudly noodles along, the song was, in Garcia’s words, about a “helpful lady, [a] big sister, kind of.” Some wondered if lines like “nobody messin’ with you but you/Your friends are getting most concerned” were about Garcia and his drug troubles. Hunter denied that rumor, but adds, “That does kind of sound like a message to him.”

A solo track Garcia rarely played with the Dead, this lovely, bobbing ballad, set in the Mission District, is the quintessential San Francisco musician’s most explicit hometown song. Hunter, who lived in the Mission when he was starting out with the Dead, penned the testimonial of a wharf-rat-style down-and-outer whose dreams once rode tall. “Tonight I would be thankful, Lord, for any dream at all,” croons Garcia before the character is baptized — first by the weather, then by a silvery downpour of guitar notes that illuminates the sorrow, loss and, yes, hope between the lines.

In the middle of the extended experimental section of his first solo album, Garcia began jamming on piano, joined by drummer Kreutzmann. Out tumbled this rollicking melody that, luckily, was captured on tape. “It wasn’t written,” Garcia said. “I didn’t have anything in mind; I hadn’t sketched it out.” Bolstered by Hunter’s cycle-of-life lyrics (written on the spot while listening to the track’s studio playback), Garcia’s overdubbed harmonies and a flowing arrangement of acoustic and pedal-steel guitars, it was so hooky that Warner Bros. released it as a single.

The core of this sprawling multipart composition is sung by Weir. But the breathtaking guitar runs that define it are pure Sixties Garcia. He sings the dark opening section (subtitled “Cryptical Envelopment”), which he wrote himself and described as “an extension of my own personal symbology for ‘Man of Constant Sorrow,’ the old folk song.” The grim verses are delivered with gentle empathy, until they ramp into the crashing instrumental section, played in breakneck 12/8 time.

For a relatively straightforward boogie, this enduring shuffle equating the symbol of America with showmen like P.T. Barnum had a somewhat tortuous history. Starting out in 1973 as “Wave That Flag,” it was dropped from the set but then revised, retitled and recorded after Garcia picked through an estimated 300 verses supplied by Hunter. “It’s a matter of carving them down to ones that are singable,” Garcia said. Although the song continued to evolve onstage, it never failed to capture Garcia’s wariness of the Man. On the Dead’s 1979 and 1980 tours, he slipped in a reference to the Shah of Iran.

Written in memory of Janis Joplin, “Bird Song” shows how, even when dealing with the most potent material (here, the death of a good friend at age 27), Garcia and Hunter could be deeply consoling without ever lapsing into the maudlin or sentimental. “Fly through the night,” Garcia instructs soulfully, “sleep in the stars.” Debuted on his first solo album, reprised on the acoustic live album Reckoning, and frequently used as the basis for a ruminative first-set jam over the years, it’s a eulogy whose Zen-like simplicity and lilting, buoyant delivery make it remarkably uplifting.

The Dead’s only top 10 hit was intended for a Hunter solo album, but Garcia heard the song and reworked it, after which it became part of the Dead’s live set. Garcia called Hunter’s original a “dry, satirical piece” about not changing with the times, but, he added, “I heard something else coming through” — namely, a hook-y “I will get by” chorus. Although the song was written before Garcia’s 1986 coma scare, many interpreted it as the story of his survival. At their first concert after his illness, Lesh remembered, “The roar of joy that greeted [Garcia] after he sang the line startled even him.”

With its wistful nostalgic evocation of a small-town family torn apart by a mother’s death (and her husband’s love for killer whiskey), this showcased some of Hunter’s most vivid lyrics. On the Europe ’72 version and subsequent live takes, it was also a forum for some of Garcia’s tastiest solos and most expressive singing, especially on the song’s bridge. “I don’t really very often relate to the characters in the songs. … Something else happens to me with Hunter’s songs that I think is more special,” he said. “And that’s the thing of them coming from a world…and I feel like I’m in that world.”

When Garcia first recorded this come-down ballad, he admitted that it was his magisterial melody that appealed to him. “I was so proud of it as a composer — ‘Hey, this is a slick song!’” he recalled. Only later in life, after his own ups and downs, did Garcia fully connect with Hunter’s lyrics about “broken dreams and vanished years,” written in New York City’s Chelsea Hotel in 1970. “That’s a good example of a song I sang before I understood it,” Garcia said. “It has a sort of brittle pathos in it that I didn’t get until I’d been singing it for a while.” Live, the Dead sometimes played so slowly it seemed to stop time.

Should deadheads be thanking Lou Reed for one of Garcia’s bounciest songs? Maybe: Garcia admitted that the melody of “Franklin’s Tower” was inspired by the doo-dooing “colored girls” part of Reed’s “Walk on the Wild Side.” An apt finale to “Help on the Way” and “Slipknot!” on Blues for Allah, the song captured a brighter, more infectious side of Garcia’s music. Hunter’s lyrics, even by his standards, are a mystery. Who was Franklin, and where was his tower? Hunter once suggested a connection between Ben Franklin, the Liberty Bell and the Declaration of Independence.

A tribute to a free-spirited hippie muse with “rings on her fingers and bells on her shoes” — in other words, the kind of girl who showed up at Dead gigs — this bouncy, jumping-bean fan favorite inspired decades of speculation on who it was about. Onstage in 2002, Hunter finally clarified the inspiration behind the song — his wife, Maureen, whom he met in England (where the song is set). For his part, Garcia turned the song into one of the Dead’s funkiest tunes. “It definitely has a little Caribbean thing to it, though nothing specific,” Garcia said. “It’s also its own thing. I think I got a little of it from that Paul Simon ‘Me and Julio Down by the Schoolyard’ thing.” The studio version was also a showcase for singer Donna Godchaux, who added an evocative wordless coda. Although Hunter generally frowned on any revisions to his words, Garcia did make one tweak to Hunter’s original lyric, changing “the love that’s in her eye” to “the look that’s in her eye.”

Perhaps the toughest tale in the Garcia-Hunter songbook, “Sugaree” began as a live Dead song but ended up anchoring Garcia’s first solo album; as with the other songs on the record, Garcia played everything here except drums (courtesy Kreutzmann). On the surface, “Sugaree” might sound like a simple ode to a dancing hippie chick. But the singer warns that the heat is coming down — and he’s already planning to cut and run, leaving her with one last request: “Please forget you knew my name.”

“Sugaree” didn’t spell out the details of their outlaw connection – a drug deal? A revolutionary cell? A prostitution ring? (Hunter only said, “The song, as I imagined it, is addressed to a pimp.”) All we know is he won’t be with her “when they bring that wagon around.” Another staple of Dead shows, “Sugaree” stands as a prescient elegy for the Sixties, exploring the desperate paranoia around the fringes of the counterculture — and hinting at the dark chill lurking behind that benign Captain Trips smile.

One of the rare instances in which Garcia wrote with bassist and resident musical theoretician Phil Lesh, “St. Stephen” beautifully blends Garcia’s sweet lyrical spiraling with Lesh’s lust for shifty time signatures and muscular improv. Although the saint of that name was a Christian martyr stoned (no, literally) for supposed blasphemy, Hunter has long claimed he was writing more about a concept than a person — and was pleasantly surprised when the band set it to what he called “this up-against-the-wall-motherfucker arrangement.” Appearing on 1969’s Aoxomoxoa — an album famously mixed with the dubious help of nitrous oxide — it reached its recorded apotheosis later that year on Live/Dead, where Garcia’s guitar truly took flight, in tandem with “The Eleven,” a Lesh-Hunter song in 11/8 time. Inextricably linked, the two were occasionally separated in performance, but that never felt right. Together, the two songs became a vehicle for some of the hottest Dead interplay ever.

Garcia was at his grittiest on this Skull & Roses track, a hard-luck dirge about hanging out by the docks and meeting a blind old boozer who asks you for a dime. The wino’s name is August West, and his story is a rough one: “Half my life I spent doin’ time for some other fucker’s crime/The other half found me stumblin’ around drunk on burgundy wine.” Although the old man swears he’ll get back on his feet someday, Garcia’s winter-is-coming guitar solo suggested harder times lie ahead — and by the end of the song, the singer realized he has way too much in common with the Rat. Despite its downbeat mood, “Wharf Rat” remained a live second-set staple right up to the band’s final shows in 1995. The Dead never tackled it in the studio — the Skull & Roses version was recorded at the Fillmore East in April 1971, with Garcia side-band sidekick Merl Saunders later overdubbing gospel-flavored organ. Garcia later titled one of his pieces of artwork after this song, suggesting how much it spoke to him.

“Bertha” was always one of the Dead’s surefire roof-raisers, often kicking off the first set with a blast of primal rock & roll boogie. As Garcia boasted when this Hunter-Garcia song was released on the 1971 live double album, always known to fans as Skull & Roses, “People can see we’re like a regular shoot-’em-up saloon band.” The character in question wasn’t actually a woman. The year after it was released, Garcia told Rolling Stone that the original Bertha was a malfunctioning electric fan in the band’s office. Since the fan would bounce across the office floor after it was turned on, it became a symbol of “whoever it is you don’t want to come around anymore.” But “Bertha” also plays on Garcia’s image as a footloose drifter, always on the run from oppressive forces. The song took on a new resonance after his notorious 1985 drug bust in Golden Gate Park: During Dead shows, the crowd would never fail to cheer wildly when Garcia sang the line, “Test me, test me/Why don’t you arrest me?”

During the festival express railway tour of 1970, which featured the Dead, the Band, Janis Joplin, Delaney and Bonnie, and others touring Canada by train, Garcia sat on the tracks one day with a copy of Hunter’s latest lyrics. Effortlessly, a fully formed song emerged; as Garcia later noted, “It just seemed to happen automatically.” Echoing Walt Whitman’s “Song of Myself” and the Bible’s 23rd Psalm, Hunter’s verses were written in England in 1970 over a bottle of Greek retsina during a productive afternoon that also birthed “Brokedown Palace” and “To Lay Me Down.” The song is nothing less than an existential sermon, with Garcia preaching as fellow traveler rather than rock messiah. “I don’t know, don’t really care,” he croons, followed by a summing-up declaration that — of all the gems Hunter penned for the singer’s woolly tenor — might as well be his epitaph: “Let there be songs, to fill the air.” While beloved by fans, “Ripple” never quite became a Dead concert staple beyond their infrequent tours with unplugged sets.

“I thought that was the closest we’ve come to what may be a classic song,” Hunter once said of this enduring standard (since covered by everyone from Lyle Lovett to Tom Petty and the Heartbreakers). It may also be the Dead’s best story song. The sheriff in pursuit of the bigamist fugitive narrator places the song in the tradition of outlaw narratives like Johnny Cash’s “Folsom Prison Blues,” Marty Robbins’ “El Paso” (a Weir-sung Dead staple) and Townes Van Zandt’s “Pancho and Lefty.” Garcia’s gently amused delivery, especially on lines like “I’ll spend my life in jail,” makes him sound more Merry Prankster than gunslinger. Tellingly, though, Hunter wrote the lyrics during early sessions with the New Riders of the Purple Sage, the country-rock outfit that briefly featured Garcia as a member. And although it was co-written with both Garcia and the New Riders’ John Dawson, it wound up as a highlight of American Beauty, perhaps the greatest iteration of the Dead’s cosmic Wild West Americana.

Garcia once said he had no special memory of writing one of the Dead’s most beautiful, exploratory jams: “I do remember that basically it wanted a samba feel,” he said. “It was kind of a Brazilian thing.” On the studio version on the band’s first self-released album, “Eyes of the World” had no distinct beginning or end, but onstage, it truly blossomed. In between verses, the Dead would routinely revel in improvisation; in later years, Branford Marsalis would often join them for it, playing up the song’s jazz roots. With Garcia’s never-sweeter leads pushing the band on, the song continued to evolve throughout the years, speeding up in tempo, and later being used as a transitional song appearing after “Estimated Prophet” more than a hundred times. “The interesting [transitions] are the ones that have a lot of interim playing possibilities, like ‘Estimated Prophet’ into ‘Eyes of the World’ — even though that’s one we do a lot,” Garcia said. “They have an interesting key relationship to each other.”

The mothership of all dead jams, which regularly stretched toward and often beyond 30 minutes, “Dark Star” was always powered by Garcia’s radiant lead lines. In the best live versions — among them, the February 1969 Fillmore West take canonized on Live/Dead and the February 1970 Fillmore East late-show journey (Dick’s Picks 4), with its jaunty sunburst at the 19-minute mark — Garcia opened melodies into melodies like a morphing fractal zoom. Hunter wrote the lyrics in 1967, the first verse arriving while he listened to the band rehearsing a new song. “The music seemed to be saying that,” Hunter recalled, “and I transcribed it.” (The remaining lines came later, written in the Golden Gate Park Panhandle, according to Hunter, after sharing a joint with a stranger.) A recording was made and released as a single in 1968, but it tanked and never appeared on a studio album. No matter: Compared to what “Dark Star” would become, it was but a road map scrawled on a napkin.

A gentle acoustic ballad with a deceptively fierce spirit, “Uncle John’s Band” sums up the soul of Jerry Garcia and how he saw himself and the Dead. With a title that references his middle name, it offers an image of a singer and his violin by the riverside, bringing a ragtag bunch of misfits and outcasts together into a community. Garcia and Robert Hunter wrote “Uncle John’s Band” at the very end of the Sixties, when their community seemed on the verge of collapse — the Dead played the finished song live for the first time in December 1969, two nights before the chaotic, death-stained Altamont debacle. (The song itself began to take shape when the Dead sent a tape of an instrumental jam to Hunter, who then wrote words to it, starting with, “Goddamn, Uncle John’s mad!”) You can hear a Latin lilt to the bongos and guitar, but the original inspiration came from elsewhere.

As Garcia recalled, “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!” With Garcia, Bob Weir and Phil Lesh joining their fragile voices to proclaim their hippie tribalism as part of a great homegrown American tradition, “Uncle John’s Band” became the Dead’s most idealistic song, but also their most resilient and defiant. As Hunter says of his 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.”