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Jerry Garcia’s 50 Greatest Songs

From country-rock gems to exploratory jams, from Grateful Dead classics to solo high-points, here’s the ultimate guide to an epic musical life

Jerry Garcia of the Grateful Dead performs at Cal Expo Amphitheatre on August 14, 1991 in Sacramento, California.

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Related: Grateful Dead Ultimate Album Guide

Just as the Grateful Dead were more than just a “jam band,” Jerry Garcia was more than just the affable Captain Trips of the scene. Over the roughly 35 years that he wrote and recorded songs with the Dead and on his own, Garcia was an uncommonly eclectic musician — equally at home with folk, bluegrass, electronic music, old-timey ballads, country, reggae, and Chuck Berry-style rock & roll. Nor was he simply “Jolly Jerry,” as his longtime lyrical collaborator, Robert Hunter, told Rolling Stone in a 2015 interview. “That man had an agony almost that he had to fight,” Hunter said. “I suppose it had something to do with losing his dad so young, and possibly his finger getting chopped off. Who knows, but there was a decided darkness to him. But you know, what great man doesn’t have that? His bright side, his ebullient side, far seemed to outweigh [it]. The darkness came into his music a lot. And without it, what would that music have been?”

All those sides of Garcia — musically and internally — emerge in this collection of the 50 greatest songs that he performed with the Dead and from his solo records.

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From Rolling Stone US

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7

“Wharf Rat,” ‘Grateful Dead’ (1971)

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.

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6

“Bertha Grateful,” ‘Dead’ (1971)

“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?”

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5

“Ripple,” ‘American Beauty’ (1970)

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.

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4

“Friend of the Devil,” ‘American Beauty’ (1970)

“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.

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3

“Eyes of the World,” ‘Wake of the Flood’ (1973)

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.”

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2

“Dark Star,” ‘Live/Dead’ (1969)

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.

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1

“Uncle John’s Band,” ‘Workingman’s Dead’ (1970)

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.”