The 20 Greatest Grateful Dead Songs of All Time

This is a list that, for years, Paste has avoided making. And I understand why. Is it actually legitimately and logically possible to rank the best Grateful Dead songs? Most signs point to no. I mean, there is likely no greater fanbase in all of rock ‘n’ roll history than Deadheads, and you can bet the whole farm on each one of them having a different idea of what the band’s greatest song is. I mean, my favorite Dead song isn’t even #1 on this list. And, with an artist that has cultivated such a prolific and important live presence, that only stirs the pot further on the discourse of it all.

But, I knew it was time to let go of the fear and just pick some really great tunes. I can put any of these 20 songs on at any given time and feel larger-than-life while also blissing out. The Grateful Dead are the greatest American rock band of all time for a reason; for nearly 30 years, Jerry Garcia, Bob Weir, Phil Lesh, Bill Kreutzmann, Mickey Hart, Keith and Donna Godchaux, Pigpen McKernan, Tom Constanten and countless more faces, names and voices have helped make the name one of the most recognizable and iconic in all of music history.

For this list, I tried to stay away from live records as much as possible, though it was impossible to avoid them completely—as some of the most important songs the band ever made never appeared in a studio capacity. So, without further ado, here are the 20 greatest Grateful Dead songs, ranked.

20. “Scarlet Begonias” (From the Mars Hotel, 1974)

The centerpiece track from their 1974 LP From the Mars Hotel, “Scarlet Begonias” is not just quintessential Grateful Dead, it’s quintessential Jerry Garcia, too. While most of Garcia’s tunes from the record had been fleshed out live on stage for a year or more prior to recording, “Scarlet Begonias” only arrived about a month before the band hit CBS Studios in March 1974. The lyrics were penned by Robert Hunter, and the story of the track is one of the richest and most ambitious in the Dead’s entire catalog—as Jerry sings about Grosvenor Square in London, gambling and even, unknowingly, foreshadows the name of Keith and Donna Godchaux’s future group, Heart of Gold Band. “Scarlet Begonias” blends psychedelia and roots rock with hints of funk and reggae fusion, and the Grateful Dead achieve that composite exceptionally well.

19. “Wharf Rat” (Grateful Dead, 1971)

I couldn’t let this list go on without a mention of “Wharf Rat,” a song that’s become synonymous with the Wharf Rats—a group of drug and alcohol-free Deadheads who used to follow the band around from city to city. It also happens to be a pretty damn great tune, too, one that was composed by Jerry and Robert Hunter and lives its best life on the self-titled live album from 1971. Merl Saunders plays a mean organ on this tune, while Jerry has a particularly choice vocal performance. “Wharf Rat” is a story of August West, a dockside wino down on his luck, but it endures as one of the best live songs in all of the Dead’s history.

18. “Brokedown Palace” (American Beauty, 1970)

You can make the argument that all of American Beauty has a place on this list, and I wouldn’t fault you for doing so—it’s a perfect record with no skips. Of course, I have to save some space for other highlights from the Dead’s extensive, wondrous catalog, but not without first making a stop here at “Brokedown Palace,” one of the greatest ballads the band ever put to tape. Sung by Jerry and exemplified by Howard Wales’ piano-playing, “Brokedown Palace” is sublime and gentle. “River gonna take me, sing me sweet and sleepy,” it goes. “All the way back, back home, it’s a far-gone lullaby sung many years ago. Mama, mama, many worlds I’ve come since I first left home.” I return to this track far more than any other Grateful Dead song, likely because it’s saccharine in a way that the band just never gets hit in the same way ever again. That’s okay, though. I prefer “Brokedown Palace” to be this tender, solemn moment of farewell and of soul’s set adrift.

17. “Mississippi Half-Step Uptown Toodeloo” (Wake of the Flood, 1973)

The opening track from Wake of the Flood, “Mississippi Half-Step Uptown Toodeloo” is a hell of a hoppin’ romp. The thing that continues to jump out at me now, after dozens (if not hundreds) of listens, is Vassar Clements’ violin. Wake of the Flood was a transitional record for the Dead, who had just lost Pigpen yet added Keith’s wife Donna Jean to the lineup. The result finds the band stepping away from their blues and folk origins for jazzy, bebop-influenced work—and you can hear the latter on “Mississippi Half-Step Uptown Toodeloo” especially, as the arrangement takes a turn towards an old rag-time jaunt packed with nautical absurdity. “They say that when your ship comes in, the first man takes the sails,” Jerry sings. “Second takes the afterdeck, the third the planks and rails. What’s the point in callin’ shots? This cue ain’t straight in line. Cueball’s made of styrofoam, no one’s got the time.” Around the 4:50 mark, the band breaks down into a great vocal harmony, the first where Donna’s irreplaceable voice shines through.

16. “Bertha” (Grateful Dead, 1971)

Though it never appeared on a studio album, “Bertha” was one of the few new tracks on the band’s self-titled live album from 1971. I know that I said I was going to be straying away from live tracks but, like, this list could not exist without “Bertha” on it. It’s quintessential Grateful Dead; a biting and surreal lover’s lament written by Jerry and recorded at Fillmore East. “Dressed myself in green, I went down under the sea,” Jerry sings. “What is going down? Try to read between the lines, had a feeling I was falling, falling. I turned around to see, heard a voice calling but it was running after me.” It’s easy to see how a track like this could outshine a live LP packed to the brim with cover songs, but the quality of “Bertha” transcends all of it. The solo from Jerry, Merl Saunders’ organ-playing, the undercurrent of bass guitar from Phil—it’s all perfect.

15. “Friend of the Devil” (American Beauty, 1970)

One of my favorite Jerry songs, “Friend of the Devil” has always been the prog-bluegrass track of my dreams. It’s as psychedelic as it is folksy, stamped into another orbit by the uptempo acoustic picking and chugging percussion from Mickey and Bill. David Grisman’s mandolin is the shining star here, as it complements the song’s outlaw story beautifully. “I ran down to the levee, but the devil caught me there,” Jerry sings. “He took my $20 bill and he vanished in the air.” New Riders of the Purple Sage bandleader John Dawson co-wrote the track, lending his idea for the story’s hook—and it remains, likely, one of the greatest decisions on all of American Beauty. Hunter’s original chorus went “Set out running, but I take my time. It looks like water, but it tastes like wine.” Dawson suggested that the second line go “A friend of the devil is a friend of mine” instead, and the rest was history.

14. “Sugar Magnolia” (American Beauty, 1970)

A Bob Weir all-timer, “Sugar Magnolia” follows “Friend of the Devil” on the tracklist and shines just a smidge brighter. There’s a reason why it’s one of the Grateful Dead’s most recognizable and beloved songs; it’s one of the best country-rock tunes of its era. The guitars on this one, wow. The outlaw themes of “Friend of the Devil” bleed into “Sugar Magnolia” sonically, and it’s one of the most effortless transitions you can find on an American rock record. It’s a sweet track rife with the wisdom of someone who’s travelled the world. “We can have high times if you’ll abide,” Bob sings. “We can discover the wonders of nature, rolling in the rushes down by the riverside.” “Sugar Magnolia” is sun-soaked and precious; a one-of-a-kind entry in a discography brimming with singularity at every turn.

13. “Franklin’s Tower” (Blues for Allah, 1975)

One of the best examples of Keith’s keyboard talents, “Franklin’s Tower” is the best song on Blues for Allah and one of the best Grateful Dead songs, period. Featuring one of the jauntiest and grooviest guitar licks I’ve ever heard and a melody inspired by Lou Reed’s “Walk on the Wild Side,” “Franklin’s Tower” boasts a favorite Dead verse of mine: “Some come to laugh their past away, some come to make it just one more day,” Jerry sings. “Whichever way your pleasure tends, if you plant ice, you’re gonna harvest wind.” It’s such a special track from start to finish, and it’s a quintessential post-hiatus offering from the Dead that should never be overlooked.

12. “Box of Rain” (American Beauty, 1970)

Written and sung by Phil Lesh (in his lead vocalist debut), “Box of Rain” was my favorite song in the world for a long, long time. This was before I’d really allowed myself to enter the Grateful Dead’s catalog in totality, but I still hold such a strong reverence for this tune. And how could someone not? It’s a perfect psych-folk song that features New Riders of the Purple Sage members Dave Torbert on bass and David Nelson on lead guitar, while Jerry plays the piano and sings harmonies with Phil and Bob. Phil wrote the track initially with Robert Hunter as a means of trying to have something to sing to his dying father, which makes lines like “Look into any eyes you find by you, you can see clear through to another day. Maybe it’s been seen before through other eyes, on other days while going home” arrive full of grief. But, backed by an Americana arrangement structure, “Box of Rain” is full of heart and compassion and daydreaming.

11. “Fire on the Mountain” (Shakedown Street, 1978)

Shakedown Street is a bittersweet album in the Grateful Dead canon, as it was the last to feature Keith and Donna and also marked the last truly front-to-back fantastic record for the band. Pull any song from the project and put it here, the sentiment will remain the same. I went with “Fire on the Mountain” because it’s just timeless and bulletproof. Written by Mickey but sung by Jerry and produced by Little Feat’s Lowell George, “Fire on the Mountain” is a Caribbean-inspired rock stunner thrown onto an album that is, in many ways, one of the Dead’s most sonically versatile and ambitious. “Almost ablaze, still you don’t feel the heat,” Jerry sings. “It takes all you got just to stay on the beat. You say it’s a livin’, we all gotta eat.” You could put “Shakedown Street” or “Good Lovin’” here and the greatness wouldn’t wither one iota. That’s the evidence that solidifies just how on top of their game the Dead were when Shakedown Street came out. Pretty remarkable stuff.

10. “St. Stephen” (Aoxomoxoa, 1969)

There’s a great rendition of “St. Stephen” on the Live/Dead album in 1969—but its original appearance on Aoxomoxoa is a real drop-dead stunner. Even today, I’d still consider it one of Jerry’s greatest guitar performances ever, as he takes a much more melodic approach while Phil bangs it out with a lot of unpredictability. Pair the two techniques together, and you’ve got one of the most psychedelic album openers in rock ‘n’ roll history. This is one of those songs that truly soars live, but the version immortalized on Aoxomoxoa opens the door for listeners to really pour over the story. “Lady finger, dipped in moonlight, writing what for?” Jerry sings out. “Across the morning sky, sunlight splatters dawn with answer. Darkness shrugs and bids the day goodbye.” There are two roads for the best Dead songs. Either you’re a classic studio version that spreads its legs marvelously on-stage, or you’re so beautiful that you can exist as tremendous without an impromptu jam. “St. Stephen” defies my logic and exists as both.

9. “Truckin’” (American Beauty, 1970)

Sung by Bob, “Truckin’” closes out American Beauty in perfect fashion—it’s one of the most unequivocally poignant codas in all of rock ‘n’ roll, as the Grateful Dead muse on all of the places they’ve been and everywhere they’re going. “Your typical city involved in a typical daydream,” Bob sings. “Hang it up and see what tomorrow brings.” The two-part guitar-playing from Jerry and Bob, too, sticks out majorly. The track takes a blues-soaked solo that chugs along behind Bob’s vocals, and it’s one of those psychedelic, cross-country emblems that only a band who’s seen the world a few times over can sing so convincingly. When you think of American Beauty, this is one of those tracks that comes to mind quickly.

8. “Uncle John’s Band” (Workingman’s Dead, 1970)

This was one of the first Grateful Dead songs I ever heard, and I still hold a great sentimentality for it. If this list was based solely on my personal preference, it’d likely rank near the top. On Workingman’s Dead, Jerry handled much of the lead vocal duties but, on “Uncle John’s Band,” he, Bob and Phil share the harmonies—and they come together to deliver a really exquisite and beautiful medley of voices. While the track doesn’t boast the stirring lyrics you might find elsewhere in the Dead’s catalog, they still register over 50 years on. “Goddamn, well, I declare,” the guitarists sing out, “have you seen the like? Their walls are built of cannonballs. Their motto is ‘don’t tread on me.’” It’s a moment that signaled the band’s studio turn towards the folk-oriented compositions that would define Workingman’s Dead and American Beauty, and it’s an unmissable and crucial part of the Grateful Dead’s legacy.

7. “Playing in the Band” (Grateful Dead, 1971)

My favorite Bob song, “Playing in the Band” is one of those tracks that just never gets old, no matter how many times I listen to it over and over. It first appeared on Grateful Dead in 1971, but I’m going with the rendition from the Veneta, Oregon concert in August 1972. This version occurred months after a polished studio recording of “Playing in the Band” surfaces on Bob’s debut solo album, Ace, and I just love it so much (and it features an incredible vocal harmony performance from Donna). The first three minutes are pure psych-blues rock, while the next 16 are just a transcendent array of jamming goodness. It’s the best of both worlds for a Dead song, really. And what makes “Playing in the Band” so crucial to the band’s catalog is that, alongside “Dark Star,” it’s a song that sparked unmistakable communal improvisation from the entire collective, not just specific members. The 1974 performance of “Playing in the Band” at the Hec Edmundson Pavilion in Seattle is even the longest uninterrupted performance in the Grateful Dead’s canon—running more than 46 minutes in length. Pick any rendition of this track you please, it’s all historic.

6. “Estimated Prophet” (Terrapin Station, 1977)

I’m a big Terrapin Station stumper, and I think “Estimated Prophet” is one of the best opening tracks in rock history, though it’s not even the best opening track in Grateful Dead history—if that even makes sense. Bob wrote and sings lead on it, but I’d be remiss if I didn’t highlight the harmonies—which are just euphoric and shine bright as Donna’s voice pierces through the montage of backing voices. “California, a prophet on the burning shore. California, I’ll be knocking on the golden door,” Bob sings. “Like an angel standing in a shaft of light, rising up to paradise, I know I’m gonna shine.” All time great horn player Tom Scott joins in on the action with a jaw-dropping saxophone and lyricon performance (in 1977 alone, Scott played sax on both this and Steely Dan’s Aja; are you kidding me?). Here, the Dead embrace their collage of prog-rock, psychedelia and jazz-rock. Here, the Dead are moving at a methodical pace yet coaxing rays of prismatic, unforgettable color out of every instrument.

5. “Eyes of the World” (Wake of the Flood, 1973)

I do think that “Eyes of the World” is one of the greatest entries into the Great American Songbook ever. It’s certainly my favorite Dead song, as Jerry and Robert Hunter deliver such beautiful musings on the wonders of the nature around us. “The heart has its beaches, its homeland and thoughts of its own,” Jerry sings. “Wake now, discover that you are the song that the morning brings. But the heart has its seasons, its evenings and songs of its own.” Featuring dueling (but complimentary) guitar-playing from Jerry and Bob, I particularly love how Keith and Donna’s harmonies shine so brightly midway through. One of the best parts about Wake of the Flood is how communal the whole record feels, and that is so clearly and glaringly evident on “Eyes of the World,” one of the finest post-American Beauty songs the Grateful Dead ever laid to tape.

4. “Dark Star” (Live / Dead, 1969)

The opening number on Live/Dead, “Dark Star” exists as an enthralling, cosmic apex for the Grateful Dead—and a thrilling final stamp of acid rock before the band took a turn towards more folk-inspired, softer and harmonious work. It was the first live album to use 16-track recording, and nothing could ever quite set the tone like the 23-minute “Dark Star,” a song so towering and auspicious that its genesis is credited to the entire band, not just Jerry or Bob or Phil. While it is true that Robert Hunter steps in for a cool spoken-word moment on the 2-minute single version of the song, we cannot overlook the 1969 Fillmore West performance that has become so synonymous with Grateful Dead lore that it would be blasphemous to exclude it from this list. From Jerry and Bob’s guitar-playing to Tom Constanten’s organ to Phil’s top-drawer basslines, this is, to me, the crown jewel of jamming. I listen to “Dark Star” and I can hear a million Deadheads being born. “Shall we go, you and I, while we can? Through the transitive nightfall of diamonds” still gives me chills every time I hear it.

3. “Casey Jones” (Workingman’s Dead, 1970)

My personal favorite story in the Grateful Dead catalog, “Casey Jones” is a song about a railroad engineer about to wreck his train while going too fast. Robert Hunter, take a bow. This one floors us all. “Trouble with you is the trouble with me,” Jerry sings out. “Got two good eyes, but we still don’t see. Come ‘round the bend, you know it’s the end. The fireman screams and the engine just gleams.” And while the song’s legacy is highlighted by that potently quotable, all-time lyric “Driving that train, high on cocaine,” it’s easy to overlook how beautiful and complex the arrangement is. It’s bluesy, folksy and downright groovy. The guitar work? My goodness, I could have the instrumental track alone playing on loop in my head for the rest of time. It’s what made Workingman’s Dead such an important pivot for the Dead, and it’s a perfect encapsulation of why 1970 was such an apex for them.

2. “Ripple” (American Beauty, 1970)

The thing about “Ripple” is that I do think that, ultimately, it’s the most beautiful song ever performed. Featuring Jerry on lead vocals, the track cascades through an acoustic soundscape backed by sublime drumming from Bill. The vocal harmonies shared by Jerry, Phil, Pigpen and Bob, too, fill out the entire space of the song, placing such unequivocal emphasis on the prettiness of the story itself. “If I knew the way, I would take you home” remains one of the greatest end lines in all of modern music, and Jerry sings it with such an inescapable, awing tenderness that it is, without a doubt, the greatest offering from American Beauty.

1. “Terrapin Station Medley” (Terrapin Station, 1977)

Whether you call it “Terrapin Station Medley” or “Terrapin Part 1,” it’s the greatest Grateful Dead track ever. Like the Beatles’ “Abbey Road Medley,” there is just something unbeatable in the formula. Mash a bunch of tracks together in a symphony of perfect songwriting and world-building and you’ll have an irreplaceable mark of modern music on your hands. The medley is comprised of “Lady with a Fan,” “Terrapin Station,” “Terrapin,” “Terrapin Transit,” “At a Siding,” “Terrapin Flyer” and “Refrain,” all of which were written by either Jerry, Mickey or Bill (with Robert Hunter, of course). Three of the seven parts are instrumental, and “Refrain” is sung by the English Choral, but what a moving 16 minutes of music it all is. “While the firelight’s aglow, strange shadows from the flames will grow ‘til things we’ve never seen will seem familiar” remains such a quintessential line, and—as it turns out—the Grateful Dead doing their best Beatles impression makes for some of the best prog-rock of all time. Not too shabby for a bunch of psych-rockers who godfathered the jam band era and have reached astral planes the rest of us could only dream of ever meeting.