The Grateful Dead share new rare footage of 1989 concert
Credit: Warner Bros.

The Grateful Dead’s 10 best songs of all time

There aren’t many bands who can match the powerful following that The Grateful Dead have enjoyed in their decades-long career. The band have built a fanbase, one famously known as the ‘Deadheads’, by making music which not only pleases the mind and awakens the body but also emboldens the soul. Below, there are ten of the band’s greatest songs of all time and it is simply the perfect start to any party.

When the West Coast of America started to populate with a nationwide swell of hippies bands began to flock to the hippie capital of San Francisco. There was sone band, however, who was born in the counter-culture movement, not simply drawn to it. That band, of course, was The Grateful Dead. They used their rock leanings and fused them with jazz, folk, R&B and just about anything else they could get their hands on, to create a sonic structure that few could match. The Grateful Dead, to put it simply, are the real deal.

The band quickly caught the attention of the globe as they became the figureheads of freeform creation and songwriting. Basking in the summer of love, the group soon gathered pace as they took their hippie stylings to the next level and rather than just looking like ‘freaks’ they acted like it too and made their live shows the centre of this spectacular band. It’s a tradition that continued throughout their career and has seen them developed a cult following that small religions would be proud of.

As good as they are on stage, and they are really good, The Grateful Dead, just like any band, still needed to sell records. It meant that 45 minute jams were all well and good but they still needed some songs to sell. Luckily, with Robert Hunter, Jerry Garcia and Bob Weir leading the way with regards to songwriting, the group were in safe hands and they delivered reams of records for their adoring audience.

For a band whose power has always been felt most intently while on stage through noodling and sprawling jams, it’s easy to forget that many of their best songs are short and sweet. Below, there are 10 of the best.

10 best Grateful Dead songs ever:

10. ‘Wharf Rat’

Taken from the band’s 1971 self-titled LP, this track, perhaps more than most, offers the key to unlocking the wonderful partnership between Robert Hunter and Jerry Garcia. Taken from their second live album Skull and Roses, ‘Wharf Rat’ depicts and down and out man only a few steps away from desperation.

It allows Hunter to get down and dirty in the realism of everyday life rather than taking his audience to another dimension altogether. The song is the beginning of the songwriting period in which Hunter and Garcia collaborated on a series of great story songs set in an America peopled by outlaws and other vagrants. A joy.

9. ‘Dark Star’

Addressing the elephant in the room, The Grateful Dead weren’t exactly the greatest band on record. Their real power came from their iconic “jams” and one song which lends itself most perfectly to these jams and therefore takes a spot on this list is ‘Dark Star’.

One of the band’s first big hits, released in 1968 and later featuring on Live/Dead the following year, ‘Dark Star’ has often been praised for its ability to carry the band into a new musical space. It quickly becomes the vehicle for musical exploration and must be considered the best because of it.

With lyrics written by Robert Hunter and music from Garcia, the track marked the band as ones to watch during their incendiary beginnings in the house parties of San Francisco. It also allowed the group to really let go and go on tangents that some bands would call entire shows. Just to prove our point he’s a 48-minute ‘Dark Star’ jam.

8. ‘Sugar Magnolia’

It’s certainly one of The Grateful Dead’s most well-known songs and it reeks of everything that made the band brilliant. Taken from American Beauty, an album which saw the group really hit their stride, the song is imbued with a powerful beauty that not many can match.

You can thank Robert Hunter and Bob Weir for the lyrics which helped to turn a sea of hippies into a fanbase known simply as Deadheads. “Sweet blossom come on, under the willow,” they sing, “We can have high times if you’ll abide/ We can discover the wonders of nature / Rolling in the rushes down by the riverside.”

7. ‘Bertha’

Taken from The Grateful Dead’s self-titled album, the track is a distillation of everything that was fascinating about the band in the early days, their deep appreciation for free-form creation underpinning the entire song. The track, not named after a mechanical fan in the band’s rehearsal room, was according to Robert Hunter, “some vaguer connotation of birth, death and reincarnation. Cycle of existences, some kind of nonsense like that.”

With this interpretation, the song manifests a much larger thematic discussion and makes references to Buddhist teachings as well as evoking the feeling of reincarnation. What’s really magical about the song, in our opinion, is the way Garcia’s takes these lyrics to brand new and impressive heights, mirroring the sentiment and providing moments of ethereal joy.

6. ‘Uncle John’s Band’

First appearing in the band’s live arsenal as early as 1969, The Grateful Dead have always kept this gem from Workingman’s Dead close to their heart. Naturally involving the Garcia and Hunter partnership, this song has become one of the band’s most famous.

Though the single saw The Grateful Dead reach some wider audiences, Garcia was particularly let down by Warner Bros.’ cut of the single and called it “an atrocity”. Later saying, “I gave them instructions on how to properly edit it and they garbled it so completely.”

With that, below there is the live version of the song instead.

5. ‘Truckin’

Prior to the release of ‘Touch of Grey’ — more on that later — ‘Truckin” was The Grateful Dead’s highest-charting single, and with good reason. The song is pumped full of guitar licks and rolling rhythm which will please any Dead fan but also comes with the delightful caveat that it was written by four of the band’s songwriters.

Few of The Grateful Dead’s songs were written this way and the nuance can certainly be heard in this robust production. A slung shuffle makes the sonic landscape of the track feel blurry but it hasn’t stopped the song being recognised as an integral piece of pop culture by the Library of Congress who included the song as a national treasure in 1997.

4. ‘Friend of the Devil’

Another track from 1970’s American Beauty sees Garcia and the rest of the band continue to use acoustic nuances to devastating effect as they match the lyrical content of the song. Apparently inspired by the band’s road manager, the track is full of tender moments and acts as a reprieve from the group’s otherwise intense sets.

The song is one of the most covered of the Dead’s tracks and according to Robert Hunter, “the closest we’ve come to what may be a classic song”. The track was performed as part of the band’s live show for some years and has been gradually slowed down over the year allowing for more keyboard and guitar solos.

However, it doesn’t get better than hearing the original, stripped back and delicately performed like no other Dead song.

3. ‘Touch of Grey’

The 1987 single ‘Touch of Grey’ is undoubtedly one of the band’s best numbers and is widely known for the iconic refrain “I will get by / I will survive” which is just an insight into the dark lyrics which belie the sounds and sonic landscape that the band create.

The joy of those lyrics is the juxtaposition they enjoy being balanced by the upbeat pop sound. With music composed by Jerry Garcia, the single remains one of the band’s few moments swimming in the mainstream—not their favourite place to be.

The song gained major airplay on MTV and saw the band’s notoriety grow once more within a new generation.

2. ‘Ripple’

If there’s an archetypal ‘peace and love’ hippie anthem then it has to be ‘Ripple’. The kind of song that asks people to leave their inhibitions and let the music flow. Away from San Francisco, Robert Hunter’s lyrics were composed in London in 1970 for this, the sixth song on The Grateful Dead’s American Beauty, ‘Ripple’.

Hunter said that ‘Ripple’ contained the lines of which he was most proud: “Reach out your hand, if your cup be empty/ If your cup is full, may it be again/ Let it be known there is a fountain/ That was not made by the hands of men.”

Garcia’s music is gentle and in-keeping of the transcendent lyrics, gently guiding you down the road and putting an arm around your shoulder as you both stride along. Drawing inspiration from the 23rd Psalm, the song is rich in texture and expert in delivery.

1. ‘Casey Jones’

If there’s one song which can hold the title of the greatest opening lyric of all time, it may well be The Grateful Dead’s classic song ‘Casey Jones. Jerry Garcia sings “driving that train/high on cocaine” and with it, he delivers a searing image of a band who has been through it all.

Of course, inspired by the train engineer Casey Jones there is no real evidence to say that he had a penchant for a few bumps. Instead, the image of Grateful Dead’s version of Jones looms heavily over the song and provides a figure of intrigue for all their fans as well as a rebel we can all get behind.

Put simply, and as it should be for any Grateful Dead greatest list, the top of the pile is the song which produces the most ‘vibe’ and ‘Casey Jones’ does that from the very beginning.

Subscribe to our newsletter
Delivering curated content