Top Ten Greatest Grateful Dead Songs

In honor of The Grateful Dead reuniting in our very own backyard for three back-to-back shows, we, at Holiday Jones, concluded a fitting tribute, and act of celebration, would be to narrow the Dead’s extensive and blistering catalogue down to ten single songs that resonate with us the most.

But before we get started on the Top Ten Greatest Grateful Dead Songs, we want to articulate some guidelines for the following list. Well, really. Just one guideline: no live songs. We’re strictly talking studio recorded tracks here. We know the spirit of the Grateful Dead, as the world’s most famous jam band, is to bust out extended, alternative versions that exist exclusively for one single night, and then are never recreated. But including such variations gives way to a convoluted list of musical nominees so far-reaching that we had no choice but to reel it in.

That being said, here’s a short list of the best live Dead cuts (in no particular order):

-“Estimated Prophet” [Live at Hartford, CT. May 28, 1977]

-“Eyes of the World” [Live at The Cow Palace. NYE 1976]

-“Touch of Grey” [Live at the Greek Theatre. July 13, 1984]

-“Ripple” [Live at Radio City Music Hall. Halloween 1980]

-“China Cat Sunflower” [Dick’s Picks Vol. 10, 1977]

-“Dark Star” [Live/Dead, 1969]


Now on to the list. If you think we’re wrong about any of these, by all means, tell us to our face on your way to the show in July.

10. “Row Jimmy” [Wake of the Flood, 1973]

For a band with widespread influences that span from country, to rock, to jazz, to psych, it’s hard to zero in on one particular archetypical Grateful Dead song, but this one incorporates and epitomizes all our favorite traits. You’ve got the loose groove with a lack of pretense, the peerless Jerry guitar lines snaking and segueing between the verse bits, sublime harmonies, and an electric piano making an “eeeeeeeeeeeeeeeee” noise throughout.


9. “Scarlet Begonias” [From the Mars Hotel, 1974]

Unlike virtually all other Grateful Dead, this song lyrically focuses on women, psychedelic drugs, and the blues. Completely unconventional stuff that they only did once in this one song and never did again. It also made for a pretty good Sublime song.


8. “Shakedown Street” [Shakedown Street, 1978]

“Shakedown Street” was the colloquial term for the parking lot outside of Grateful Dead shows epitomized by weed brownies, veggie burrito farts, and really gross blonde dreadlocks. But the title track from Shakedown Street calls to mind none of those. Instead, it just sounds like a harmonious mixture of disco and cocaine.


7. “Dire Wolf” [Workingman’s Dead, 1970]

By and large, most Grateful Dead songs are about nebulous concepts of love and death that are either completely shrouded in metaphor, or generally about cowboys. But on Dire Wolf, Hunter and Garcia leave this planet and travel to Middle Earth where they tread on song subject territory more commonly tackled by the likes of Zeppelin, Dio, or George R.R. Martin.


6. “St. Stephen” [Aoxomoxoa, 1969]

This rock n’ roll juggernaut of a song, co-written by bassist Phil Lesh, is about a First Century Christian prophet who was stoned to death. No, Deadheads. Not that kind of stoned. It also features a lot of screaming in the background which we think is cool.


5. “Black Peter” [Workingman’s Dead, 1970]

When you give this song an initial casual listen, it sounds like plain ol’ good vibes. But if you actually listen to the song, you realize it’s an epic bummer. Probably John Barlow biggest bummer is his whole career of bummer songs. It’s about a guy slowing dying while his friends hang out and watch.  Eat your heart out, Morrissey.


4. Friend of the Devil [American Beauty, 1970]

This is a classic Dead track off a classic Dead album that epitomizes classic rock. It’s a textbook amalgam of lenient rock and Appalachian-sounding swagger with a narrative coalescing 3:10 to Yuma and The Devil and Daniel Webster. The basic takeaway is that sins must be atoned for, man.


3. Althea [Go to Heaven, 1978]

Sort of like Pennywise’s “Bro Hymn“, this song is about one of the band members being dead before he is actually dead. When it was released on Go To Heaven (hint hint) in 1980, it was probably interpreted by most listeners as a cracking funk jam involving Mother Earth and Shakespeare. But in light of the death of Jerry Garcia, it’s lyrics about a goddess warning against self-indulgence and spiritual emptiness, are clearly a thinly veiled attempt by creative collaborator, Robert Hunter, to save Jerry Garcia from the drug addiction that would ultimately take his life.


2. Cassidy [Ace, 1972]

Yes, this song is technically from a Bob Weir “solo” album, but that was basically in name only. Flip over to the back of Ace and you’ll see Weir’s backing band includes contributions from every Grateful Dead member at the time (including lyricist John Barlow). The whole album is excellent, and this song, in particular, became a Grateful Dead setlist staple, for good cause.   Most notably here.


1.Ripple [American Beauty, 1978]

At this point in the Grateful Dead’s existence, it’s difficult to wade through the sea of cultural and arty baggage to get a genuine feel for the band. On one hand, you have the social trappings that went along with the band: the hippies; the Peace & Love Movement; the recreational drug use; and overall jam band scene. On the other hand, you have the music itself, which is really the instrumentation of two different songwriters working independently (Garcia and Weir) and two different lyricists working independently (Barlow and Hunter), and therefore, the catalogue is sprawling in its variety.

These dynamics can leave the listener with an impression of the Grateful Dead that falls somewhere between artificiality and straight up weirdness.

But “Ripple” finds the band at its most genuine condition. On this track, more than any other, the band peels back the layers of metaphor and irony to reveal a light, optimistic, masterpiece without an ounce of cynicism or pretense. The mandolin melody and cascading strings carry the sage-like lyrics to heights few bands other than the Grateful Dead are capable of going to.


BONUS:  In light of Trey Anastasio filling in for Jerry, we’d be remiss to not include our favorite Phish song.

“Backwards Down the Number Line” [Joy, 2009]