Top 10 Grateful Dead Songs by Bob Weir

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In the scope of classic rock and of popular music as a whole, Grateful Dead vocalist/guitarist Bob Weir can be seen as an outlier of sorts. A truly singular presence, even within the context of his own band, the distinct tonality of both Weir’s guitar playing and vocals lend his output an unmistakable quality that is, quite frankly, irreplicable.

Despite the overwhelming perception of guitarist/vocalist Jerry Garcia as the leader and frontman of the Grateful Dead– roles to which Garcia himself would refuse to lay claim throughout his career – Bob Weir would establish himself early on as a lead vocalist and creative contributor. In fact, some of the most enduring material to be associated with the Grateful Dead emerged, at least in part, from the creative mind of Bob Weir.

Many of the most frequently performed songs performed by the band feature Bob Weir at the forefront, and today, ClassicRockHistory.com will be taking a look at the Top 10 Grateful Dead songs by Bob Weir.

# 10 – Hell in a Bucket

By 1987, the Grateful Dead were – knowingly or otherwise – in their final decade of existence as a band. It is ironic then that this would be the point during which the band would ascend to the commercial mainstream on the back of the Garcia/Hunter tune, “Touch of Grey,” which would become the band’s first number one single and would propel its parent album, In the Dark to multi-platinum status.

“Touch of Grey” was followed up by “Hell in a Bucket,” a curious Weir/Barlow/Mydland collaboration featuring allusions to bikers, chrome-spiked suspenders, Catherine the Great, and boots of champagne. An anomaly of sorts in the Discography of the Dead, “Hell in a Bucket” utilized the same types of angular chord changes to which Jerry Garcia would purportedly refer to as having been used in Bob Weir’s “Victim or the Crime,” which would be released as part of 1989’s Built to Last.

The song itself, a light-hearted but also slightly intense romp, was paired with an equally zany music video featuring farm animals, circus performers, BDSM, and Bob Weir in a lavender blazer that just screams “80s.” The sheer unusualness of the song’s structure and bizarre accompanying video makes it an ideal vehicle for Bob Weir’s trademark sardonic vocal affectations.

# 9 – Good Lovin’

Despite having been recorded originally by The Young Rascals and bringing the band a number one hit, the Grateful Dead essentially co-opted the song as their own in the early days of their career. The song was initially sung by founding keyboardist/vocalist Ron “Pigpen” McKernan as part of his “rave-up” performances and would continue to be a mainstay of the group’s live act even after McKernan’s passing.

Bob Weir would take up the mantle as lead singer for the tune, which the Grateful Dead recorded as part of their 1978 studio album, Shakedown Street. The band performed “Good Lovin’” on Saturday Night Live that same year, and the song would ultimately become one of the most frequently performed songs in the history of the Dead.

# 8 – Looks Like Rain

Recorded as part of Bob Weir’s 1972 solo album Ace, on which he is backed by fellow members of the Grateful Dead, “Looks Like Rain,” like much of the album’s material, would be incorporated heavily into the band’s performance repertoire.

The sessions for Bob Weir’s solo album marked some of the earliest instances of what would become an ongoing collaboration with lyricist John Perry Barlow. “Looks Like Rain” would become an uncharacteristic example of a “torch song” performed by the Grateful Dead, a band that generally eschewed conventional odes to significant others, love lost, and other general tropes prevalent in popular music.

Still, the tune itself avoids the traps generally associated with this type of writing, with Weir implementing plenty of characteristically wonky chord voicings and the band making the most of instrumental dynamics and interplay.

# 7 –  Lost Sailor/Saint of Circumstance

Technically two songs – which were released as part of 1980’s Go to Heaven in an opening sequence for Side 2 of the album – “Lost Sailor” and “Saint of Circumstance” would be presented almost exclusively as a pairing during live performances. Another Weir/Barlow concoction, the sequence is indicative of a certain musical drama that Weir was capable of bringing to the generally loose and abstract aesthetic of the Grateful Dead.

The lyrics explore themes of uncertainty and longing, notably inverting the trope pertaining to the freedom of the open ocean to address the limitations and confines of the freedom in question once it is achieved. Much in the same way as “Looks Like Rain” or “Estimated Prophet” – more on that later – “Lost Sailor/Saint of Circumstance” would also offer up a degree of musical variety in a live setting, providing a jumping-off point from which the band could explore the sonic backdrop which consisted in no small part of minor to major seventh chord variations.

# 6 –  Playing in the Band

Though Bob Weir’s primary songwriting collaborator throughout the career of the Grateful Dead would be his friend, John Perry Barlow, there are a number of instances in which Bob Weir’s name can be seen paired with that of the great Robert Hunter, a key Jerry Garcia collaborator who also assisted in the writing of bassist Phil Lesh’s signature tune, “Box of Rain.”

“Playing in the Band” marks one such instance, as lyrics for the live staple were penned by Hunter while the music was composed by Bob Weir with input from drummer Mickey Hart. However, during a 2/12/2021 live stream performance by Bob Weirr and Wolf Bros from TRI Studios, much to the surprise and excitement of drummer Jay Lane, Weir revealed a fourth, previously unnamed contributor to the iconic tune.
“This one I wrote a long time ago,” began Weir during the livestream. “Actually, David Crosby came up with the seminal lick, and then he left. We were out at Mickey’s barn, so Mickey says, ‘make a song out of that.’” The next day, I had it.”

Originally released as part of the band’s self-titled 1971 album – colloquially known as Skull and Roses among fans – “Playing in the Band” was another song strongly associated with the Grateful Dead that is technically a solo number, having appeared on Bob Weir’s own album Ace in 1972. The song would be played hundreds of times onstage by the Grateful Dead, and was frequently utilized as a vehicle for extended jams and instrumental solo sections.

# 5 – Weather Report Suite

There’s a lot to unpack with “Weather Report Suite,” initially released in 1973 as part of Wake of the Flood, the first in a string of noteworthy and arguably underappreciated studio LPs to be released by the band throughout the 1970s.

As the name would suggest, the piece is a medley of sorts comprising three sections: Prelude, Pt. I, and Pt. II (Let it Grow). The unaccompanied guitar intro speaks to the influence that jazz pianists such as McCoy Tyner and Bill Evans have had, by Bob Weir’s own admission, on his guitar playing and songwriting technique. The track sees the rest of the band join in as a lush sonic atmosphere overtakes proceedings. In fact, up until the unveiling of the song’s final section, it doesn’t sound all that different from something one might hear on Dark Side of the Moon.

The song’s final act, so to speak, brings with it an increased intensity, which also entails a more frantic tempo. From here, Weir and Barlow wax poetic with no shortage of biblical allusions, statements of grandeur and, fittingly, references to the weather. Perhaps more prog-leaning than what listeners had come to expect from the Dead at the time of its release, “Weather Report Suite” stands as one of the most prominent examples of Bob Weir’s idiosyncratic input providing an effective counterpoint to Jerry Garcia’s compositional proclivities, thus endowing the Grateful Dead with an expanded musical dimension.

# 4 – Estimated Prophet

Written by Bob Weir with John Perry Barlow, “Estimated Prophet” opens 1977’s Terrapin Station in characteristically trippy fashion. The song is performed in septuple time, augmenting the sense of unease fostered by the strange chord voicings and ominous lyrics heard throughout.

“The album kicks off with “Estimated Prophet,” which is a Weir/Barlow creation,” writes drummer Bill Kreutzmann in his 2015 memoir, Deal: My Three Decades of Drumming, Dreams, and Drugs with the Grateful Dead. Kreutzmann explains how the song’s unique time signature came to be, stating,

“It’s a great song, but when he brought it to us, something was off. It needed a groove. It was in quick 7/4 but it didn’t swing…yet. For my homework that night, I combined two fast sevens and played halftime over it. The two sevens brought the time around to an even number. The phrasing is in two bars of seven, so technically the time signature is in 14/8, but that’s getting technical. In layman’s terms, “Estimated Prophet” suddenly grooved.”

Lyrically, the tune takes on the perspective of an overzealous and debatably delusional character who believes himself to be a sort of grand, cosmic force. Inspiration for the lyrics is said to have been taken, at least in part, from the raving, drugged-out individuals which would intersect with the Grateful Dead crowd scene from time to time. In typical Barlow fashion – and in keeping with the theme of the song – “Estimated Prophet” is rife with biblical imagery and references to various weather-related events.

“Estimated Prophet” is another song that could potentially come across if offered by another artist, but that relies on Bob Weir’s idiosyncratic delivery and personification of the title character to transcend its own station as a recorded piece of music and embody the grandeur detailed within.

# 3 – The Other One

Though it would come to be known as a standalone performance piece sung at shows by Bob Weir, what many recognize today as “The Other One” has its origins as a section of a larger, multi-part piece known collectively as “That’s It for the Other One” released on the second Grateful Dead album, Anthem of the Sun.

The song’s third section, “The Faster We Go, the Rounder We Get” would become a mainstay of the band’s live shows and would be billed simply as “The Other One” on releases such as Live at Red Rocks Amphitheatre and Grateful Dead (Skull and Roses). Other sections of the full song were performed live in varying capacities throughout the career of the group, and the song itself is a notable instance of temporary keyboard player Tom Constanten’s having received a writing credit on a Grateful Dead album.

Performed live, “The Other One” frequently featured extended sections for jamming, most notably during the intro section which would often include extended passages from drummers Bill Kreutzmann and Mickey Hart.

The song is significant also in that it contains substantial lyrical contributions from Bob Weir, who was primarily a compositional contributor to the band’s music. Bob Weir himself has acknowledged the influence of writer and Beat Generation icon Neal Cassady on the song, and even alludes to Cassady in the lyric, “There was Cowboy Neal at the wheel of the bus to never ever land.” Cassady himself was close with the band and even lived with the members at 710 Ashbury for a time prior to his death in 1968.

Other notable lyrical bits include an autobiographical reference from Bob Weir detailing an incident during which he had struck a police officer with a water balloon.

“The heat came ‘round and busted me for smiling on a cloudy day,” goes the passage, one of many throughout the song to utilize psychedelic imagery and abstract metaphors consistent with the period of the song’s composition.

# 2 – Sugar Magnolia

Another of Bob Weir’s handful of collaborations with Robert Hunter, “Sugar Magnolia” became a go-to for the Grateful Dead in a live setting, having been performed more times than nearly any other number in the band’s history. Originally included as part of 1970’s American Beauty, the song would morph and change once taken on the road, as was typical of the band’s material.

It would eventually comprise two distinct parts: “Sugar Magnolia” and “Sunshine Daydream,” the latter designation taken from a lyric in the original song’s final verse. “Sunshine Daydream” would generally serve as a canvas upon which members of the band could engage in extended, collaborative jam sequences. The time between sections varied from performance to performance. At times the transition would be direct or comprise but a handful of measures, other times entire sets would fall between the two sections. “Sunshine Daydream” was once famously launched into a full week after the conclusion of “Sugar Magnolia.”

In its original studio-recorded form, however, “Sugar Magnolia” remains one of the Grateful Dead’s most accessible songs. With the relatable subject matter, a catchy melody, and a tight three-minute and eighteen second runtime, the song is stylistically indicative of its parent album, which remains one of the most popular Grateful Dead albums, particularly to the casual listener.

# 1 – Jack Straw

“We can share the women, we can share the wine,” opens what could arguably be called the finest collaboration between Bob Weir and Robert Hunter. Like “Brown-Eyed Women,” “Tennessee Jed,” and “Ramble On Rose,” “Jack Straw” wouldn’t have sounded out of place on 1970’s American Beauty, and was conceived during what some believe to be sessions for a follow-up album assembled in the same vein which never materialized.

Many of these previously unheard gems would emerge during the Grateful Dead’s now-legendary European tour run in 1972 which was fittingly documented as part of the live triple-album, Europe ’72. Despite members generally taking vocals on songs that they had written – much in the same way that The Beatles were known to have dictated which member sang lead on which songs – “Jack Straw” is unique in the live performances of the song would often find Bob Weir and Jerry Garcia swapping lead vocal duties in different sections.

“We used to play for silver, now we play for life. One’s for sport and one’s for blood at the point of a knife,” goes one verse lyric in a Hunter offering containing a wealth of the writer’s signature references to trains, gambling, and old America. A frequent opening number in Grateful Dead sets, “Jack Straw” would be elaborated upon during later performances during which the band would work its trademark jam sequences in during the song’s outro section.

Top 10 Grateful Dead Songs by Bob Weir article published on Classic RockHistory.com© 2023

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