The 20 Best Grateful Dead Songs of All-Time

The Grateful Dead

Any article about the Grateful Dead eventually has to tackle the elephant in the room. The Grateful Dead’s fusion of rock, psychedelia, jazz, folk, R&B, and whatever else had tickled their fancy that week didn’t always work on studio recordings.

Where it did work was on the stage. When they locked and loaded into one of their epic live jams, there was no one else quite like them. These are the 20 best Grateful Dead songs that helped them become such iconic performers.

20. Stella Blue

Kicking off our list is Stella Blue, a comedown ballad with a slick melody from Jerry Garcia and some superbly emotive lyrics about “broken dreams and vanished years” from Robert Hunter.

19. Franklin’s Tower

Garcia “borrowed” the melody for Franklin’s Tower from Lou Reed’s Walk on the Wild Side. Considering how good the result is, we doubt even the famously curmudgeonly Reed grumbled too much. Hunter’s lyrics are as obtuse as ever, but overall, it’s a slice of pure pop magic.

18. Scarlet Begonias

A mid-tempo number with a laid-back groove and an infectious hook, Scarlet Begonias is a psych-pop gem. The lyrics are a bit hippie-dippy (“She had rings on her fingers and bells on her shoes / And I knew without asking she was into the blues / She wore scarlet begonias tucked into her curls / I knew right away she was not like other girls”) but this was the 70’s and this was the Dead… what else would you expect?

17. Touch of Grey

By the 1980s, Garcia’s addictions had begun to take their toll. In 1986, he slipped into a diabetic coma for 5 days. It had a profound impact on him, forcing him to relearn basic motor skills and go back to the drawing board on the guitar.

But he persevered, and within a few months, he was back on the road. The following year, the band released In the Dark, their best-selling album of all time. One of its highlights is Touch of Grey, a sweet ode to survival that gave the band an unexpected Top 10 hit.

A lesser song might have lost its charm to ubiquity, but no matter how often it’s played in waiting rooms, shopping malls, and hair salons, that classic line of “I will get by… I will survive” still resonates.

16. Wharf Rat

When Robert Hunter and Jerry Garcia came together, magic happened. On Wharf Rat, Hunter leaves aside the mysticism and circle of life musings for the day and gets real. His story of a down-and-out drunk who’s only a dime away from desperation is complemented perfectly by Garcia’s hard and gritty guitar work. It’s a downbeat classic, and one that, while never officially recorded, became a staple at concerts for years after.

15. The Wheel

According to Rolling Stone, The Wheel was written in the middle of the extended experimental section of Garcia’s solo album. He started jamming on the piano, Bill Kreutzmann jumped in with some percussion, and between the two of them, they managed to come up with one of the Dead’s most outrageously catchy melodies.

It wasn’t written down, but fortunately, it had been captured on tape. Hunter added some lyrics about the circle of life, Garcia added in some pedal steel guitars, and Warner Bros were so flawed by its hook, they released it as a single.

14. Dark Star

The Grateful Dead weren’t at their best in the studio. It was on the road that they excelled. Their never-ending tour of the 80s and early 90s might have been promoted more by Jerry Garcia’s drug bills than anything else, but even when he was clearly in no fit shape for anything but rehab, the band could still bring the house down with their jams.

Dark Star is a song that lends itself to sonic explorations. It was fine when it was released as a studio single in 1968, but it’s the live version from the following year’s Live/Dead that really wows.

According to Wikipedia, the song has been included on The Rock and Roll Hall of Fame’s 500 Songs that Shaped Rock and Roll list and was ranked at number 57 on Rolling Stone’s 100 Greatest Guitar Songs of All Time. If you need help figuring out why, just give it a listen.

13. Bertha

When the Grateful Dead wanted to raise the rafters, they had the song to do it. Bertha is a primal piece of rock and roll that sums up everything we came to love about the band in their earliest days.

There’s the rich textures, the slightly obscure lyrics (this time around, the story is told from the perspective of a man who’s run from a relationship and is very keen that his lover doesn’t follow him – “I had to move / Really had to move / That’s why if you please / I am on my bended knees / Bertha don’t you come around here anymore”), the blistering guitar licks, and a freewheeling energy that’s utterly joyous.

According to Song Facts, Hunter once said the song is about “some vaguer connotation of birth, death, and reincarnation. Cycle of existences, some kind of nonsense like that.” If he sounds vague, he’s got a right to. It was nearly 50 years ago. Ultimately, what it’s about doesn’t matter so much. It could be about a puddle and that hook would still get us.

12. Eyes Of The World

As All Music writes, Eyes Of The World quickly became a cornerstone in the Dead’s live repertoire after its release in 1972, and for good reason. Its jazzy, open-ended style is a far cry from the rowdy, bluesy numbers of their earlier days, but it was the perfect launchpad for one of their legendary half-hour jam sessions.

An uptempo, deliciously catchy number, it ushered in the Dead’s jazz age. It didn’t last long – by the late 1970s, they’d gone disco (or as disco as the Dead could conceivably get) – but it was exhilarating while it lasted.

11. Sugar Magnolia

Taken from 1970’s American Beauty, Sugar Magnolia ranks as one of the Grateful Dead’s best-known and most popular songs. Combining a rich texture with expert delivery, it has all the shimmering sweetness and feel-good vibes of the Dead at their hippie best. This was the album that turned an army of flower children into Deadheads, and this is the song that made a generation pack up their VW’s and head for Haight Ashbury… or at least, wish they could.

10. Fire on the Mountain

Originally released on the 1978 album Shakedown Street, Fire on the Mountain sees the band abandon peace and love for the day and descend into a dark place where “Almost ablaze still you don’t feel the heat / It takes all you got just to stay on the beat / You say it’s a living, we all gotta eat / But you’re here alone, there’s no one to compete.” A shimmery guitar keeps things just the right side of pop.

9. Cassidy

On the one hand, Cassidy is an elegy to beat hero Neal Cassady, the central inspiration for the character of Dean Moriarty in Jack Kerouac’s “On the Road.” On the other hand, it’s a greeting to Cassidy Law, Dead sales manager Eileen Law and Dead roadie Rex Jackson’s newborn baby boy. An insightful take on the circular nature of life and death, it was never officially recorded by the Dead, but still managed to become one of the most popular fixtures at their live shows.

8. Ripple

Don’t listen to Ripple with your 21st-century hat on. This isn’t a song for the cynical, it’s not a song for the sarcastic, and it’s definitely not a song to listen to if you’ve got a grudge against hippies. Widely considered to be the ultimate peace and love song, it’s a tune that demands you leave your inhibitions at the door and get swept up in the love.

The pseudo-mysticism requires a special set of ears to take seriously, but if you can tap into your inner flower child, you’ll struggle to find a brighter, more jubilant celebration of life, love, and music.

7. Althea

Althea manages to combine a laid-back, breezy chug with some right-on messages about spiritual decay, shortsightedness, and failing to learn from the lessons of history. Considering how far Garcia had sunk into addiction by that point, some people have suggested it’s Hunter’s subtle attempt at an intervention.

6. Loser

Hunter and Garcia always did have a fondness for a no-count gambler. The anti-hero of Loser is a deluded deadbeat who’s “got no chance of losing this time.” One final win, and then it’ll be the straight and narrow forever after.

As Stereo Gum says, it’s a tale as old as Mickey Spillane, Alfred Hitchcock, or Michael Corleone, but somehow, Loser manages to tell the story so vividly, you forget you know how it ends.

5. Friend of the Devil

American Beauty isn’t exactly short on classic tracks, but Friend of the Devil might just trump the lot. In essence, it’s a simple, straightforward acoustic song about a man on the run from the law, the devil, and himself.

Obviously, this being the Dead, things aren’t quite as simple as they seem, but as Hunter himself said, this is “the closest we’ve come to what may be a classic song.” If you ever wondered what would have happened if the Dead had continued exploring the country sounds of Workingman’s Dead, this is it.

4. Truckin’

As writes, Truckin’ was the Grateful Dead’s highest-charting single before Touch of Grey came along 16 years later and smashed its record. The reason for its success is simple- it’s a stunning song, chockfull of killer guitar licks and rolling rhythms.

The fact that Jerry Garcia, Bob Weir, Phil Lesh, and Robert Hunter all contributed to its lyrics might have helped some too. In 1997, the Library of Congress recognized the song as a national treasure, and very rightly so.

3. St. Stephen

Who else could tell the story of the last days and trial of the New Testament’s very first martyr, St. Stephen, other than the Grateful Dead? An extraordinary piece of songwriting with some rare lyrical contributions from bassist Phil Lesh, it’s as wild and heavy as the Dead ever got. The live version from the 1969 album Live Dead is particularly apocalyptic.

2. Uncle John’s Band

In 1970, the Grateful Dead were at the peak of their powers. Taken from the album Workingman’s Dead, Uncle John’s Band showcases their superb song crafting abilities, combining strong melodies with stripped-back arrangments and the kind of harmonies that wouldn’t sound out of place on a Crosby Stills and Nash track.

Factor in lyrics that draw on the social upheavals of the time while also referencing Irving Berlin, obscure mountain tunes, and even the Gadsden Flag of the American Revolution, and you’re looking at one of the strangest but most beautiful songs in the Grateful Dead canon.

1. Casey Jones

Even if you’re not a hardcore Deadhead, there’s a good chance you’ll know the opening line to Casey Jones. If ever there was a song with a better introduction than “Drivin’ that train/ High on cocaine,” it’s yet to be found.

Apparently, the song is based on real-life train engineer Casey Jones. There’s no actual evidence to suggest he indulged in the kind of practices the Dead implied he did, but sometimes, fiction is better than fact, and in this case, the evocative portrait of a mysterious rebel propels the song to No.1 on our list of the greatest Grateful Dead songs of all time.

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