The Grateful Dead – The Faster We Go, the Rounder We Get / The Other One (1968)

The Dead’s love for the road is in evidence on this segment from That’s It for the Other One, the four-part opening track of their second LP, Anthem of the Sun. A rare Bob Weir-penned lyric details the Dead’s youngest member being busted by the cops “for smiling on a cloudy day” – referencing a real-life incident when Weir pelted police with water balloons as they conducted what he took to be illegal searches outside the group’s Haight-Ashbury hangout. It then connects with the band’s spiritual forebears the Merry Pranksters by referencing Neal Cassady, driver of “a bus to never-ever land”. The song later evolved into The Other One, one of the Dead’s most played tunes and a launchpad for their exploratory jams – as in this languid, brilliant version at San Francisco’s Winterland in 1974.

The Grateful Dead – Truckin’ (1970)

“What a long, strange trip it’s been,” reflected Weir on what is arguably the Grateful Dead’s anthem. The group were only half a decade into a remarkable 30-year career when lyricist Robert Hunter penned this picaresque of their touring escapades. It’s heavy on the gnarly details – groupies consumed by “reds, vitamin C and cocaine”, and endless hotel-room drug-busts – but the Dead’s spirited delivery and, in particular, Weir’s jovial growl, located the magic in their peripatetic lifestyle. As with many Dead tunes, Truckin’ was best heard in concert (or on a fan-taped bootleg traded in the car park before a show). The rumble captured at London’s Lyceum on the Europe ’72 live LP is as fine as any you’ll hear.

The Grateful Dead – Sugar Magnolia (1971)

A tribute to Weir’s longtime paramour Frankie Hart – “a summer love in the spring, fall and winter” who could “make happy any man alive” – and a highlight of their 1970 LP American Beauty, Sugar Magnolia showcased the Dead’s embrace of Americana and songcraft. Their second most played song evolved a joyful coda in concert, Sunshine Daydream, and it was often the first song they would play after the clock struck midnight at their New Year’s Eve concerts. The performance at San Francisco’s Winterland Ballroom on 31 December 1978, marking the closure of the venerated venue, is a true Deadhead favourite.

Bob Weir – Playing in the Band (1972)

Playing in the Band portrays the Dead’s lifestyle as some quasi-mystical vocation, with the narrator a talk-is-cheap road warrior who has developed his own philosophies along the way: “I don’t trust to nothing / But I know it come out right.” Evolving from a riff coined by David Crosby during a jam in Dead percussionist Mickey Hart’s barn, the track first surfaced on the Dead’s eponymous 1971 live LP, then featured on Weir’s 1972 solo debut Ace, before the group reclaimed it as a vehicle for their most questing, open-ended excursions. The legendary 46-minute version from Seattle’s Edmundson Pavilion in 1974 is reckoned to be the longest song performance the Dead ever pulled off.

Bob Weir – Cassidy (1972)

Named for the young daughter of a Dead roadie, Cassidy doubles as a tribute to beat poet Neal Cassady, whose restless, questing example cast a long shadow for Weir. A lilting, upbeat folk-rocker, it finds Weir offering the infant Cassidy life lessons he has drawn from Cassady’s quixotic lust for freedom, singing on the coda: “Let your life proceed by its own designs … Let the word be yours.” This sentiment, along with the pearlescent, folky tangle of a riff, made Cassidy a song Weir revisited throughout his career, with the Dead and also with RatDog, the group he formed following Garcia’s death in 1995.

The Grateful Dead – The Music Never Stopped (1975)

Is 1975’s Blues for Allah the funkiest Dead album? The Meters-esque swing of Jerry Garcia’s Franklin’s Tower suggests as much, as does this Weir-penned reverie, steeped in the rhythms of the south. The Music Never Stopped is driven by Weir’s prickly guitar figures, stirring up a groove that wouldn’t have shamed Allen Toussaint, while the sparring harmonies with singer Donna Jean Godchaux give this playful number a Bourbon Street-worthy earthiness. The down-home imagery, co-written with Weir’s regular collaborator John Perry Barlow, verges on the hokey, but if you aren’t seduced by the “rainbow full of sound … fireworks, calliopes and clowns”, that’s your loss.

Kingfish – Lazy Lightning/Supplication (1976)

After the Dead temporarily ran aground in the mid-70s, Weir jumped ship to join his pal Matthew Kelly’s group Kingfish, for whom he wrote this luminous two-parter mixing imagery of lust and addiction. The studio version, all pristine harmonies and succinct, FM radio-ready AOR, is charming. But as is always the way with Dead-related music, the song truly came into its own after the group reformed and Weir added it to their setlists. Performances such as this one from the Sportatorium in Florida in 1977 unlocked the conversational, jazzy potential that is only hinted at on Kingfish’s studio original.

The Grateful Dead – Estimated Prophet (1977)

“The Grateful Dead play reggae” may be a hard sell as a concept, but Estimated Prophet is something else. The track possesses a menace that is rare in Dead music, with Weir portraying a darkly charismatic Manson-like figure duelling with the voices in his head and threatening to “call down thunder” and “fill the sky with flame”. The portrait is grimly compelling, the band doubtless having crossed paths with many such drug-damaged characters as the 60s soured. Fans cite the 1990 recording from New York’s Nassau Coliseum as the keeper, with guest musician Branford Marsalis playing lyrical saxophone, but the song’s dark heart is perhaps best represented on the recording of their 1979 show at Oakland Auditorium Arena, where Weir’s choppy guitar lends a foreboding undertow to Brent Mydland’s sprawling keyboard solo.

The Grateful Dead – Lost Sailor (1980)

The Dead seemed mostly unconcerned by whatever trends were moving the mainstream. During their tenure at Clive Davis’s Arista records, however, the storied record mogul teamed them with outside producers, hoping to connect the Dead, however reluctantly, with the zeitgeist. The sleeve of 1980’s Go to Heaven, with the group in white disco suits and flowing tresses as if they’d hired the Bee Gees’ stylists, suggested an uncharacteristic misstep. But the album itself has aged well, in particular this meditative and melancholic number. On Lost Sailor, a disillusioned Weir recognises himself in the figure of a haggard old boatman as dedicated to the sea as the singer and guitarist is to the open road, musing “freedom don’t come easy”.

The Grateful Dead – Hell in a Bucket (1987)

The Grateful Dead’s only US Top 10 LP, 1987’s In the Dark, is far from beloved among Deadheads. But while a goofy, skeleton-packed video briefly sold these boomers to the MTV generation, this cynical kiss-off to a former lover proved the Dead hadn’t sacrificed their dark wit for stardom. The narrator plays like a character from a Steely Dan song, a loser nevertheless focused on having the last laugh, as Weir’s Dylanesque croak depicts his ex as “the reincarnation of the ravenous Catherine the Great” and reasoning, in the irresistible hook, “I may be going to hell in a bucket, babe, but at least I’m enjoyin’ the ride”. It’s a timeless sentiment, even if the gonzo music video featuring Weir in a pastel suit straight out of Miami Vice, and his leather-clad ex, has not aged so well – though Bob is clearly having fun throughout.