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Greatest Stories Ever Told - "Lost Sailor" & "Saint Of Circumstance"

By David Dodd

Here’s the plan—each week, I will blog about a different song, focusing, usually, on the lyrics, but also on some other aspects of the song, including its overall impact—a truly subjective thing. Therefore, the best part, I would hope, would not be anything in particular that I might have to say, but rather, the conversation that may happen via the comments over the course of time—and since all the posts will stay up, you can feel free to weigh in any time on any of the songs! With Grateful Dead lyrics, there’s always a new and different take on what they bring up for each listener, it seems. (I’ll consider requests for particular songs—just private message me!)

“Lost Sailor”

“Saint of Circumstance”

“This must be heaven” pretty much sums up my life philosophy. As far as we know, it’s all we’ve got, and you have to admit, it’s a pretty amazing place, this planet we’re on, and these bodies we get to occupy for whatever amount of time we have.

This pair of Bob Weir / John Barlow songs manages to get at a number of major Grateful Dead themes and motifs within their space. Ambiguity (“Sure don’t know…); rainbows; cats (“tiger in a trance”); weather; gambling (‘odds against me…”); and I’m sure I’m missing something.

“Lost Sailor” and “Saint of Circumstance” were written in Mill Valley in July 1979.

The band first performed the pair of songs on August 31, 1979, at Glens Falls Civic Center, in Glens Falls, New York. “Lost Sailor” debuted earlier that month, on the fourth of August, at the Oakland Coliseum Arena, and was played four times on its own prior to August 31. “Saint” was played mostly (but not always!) in a pair with “Sailor” until March 24, 1986, at The Spectrum in Philadelphia, after which “Sailor” was dropped permanently from the rotation. “Saint” remained in the rotation thereafter. Its final performance was on July 8, 1995, at Soldier Field. “Lost Sailor” and “Saint of Circumstance” appeared on Go To Heaven, released in April 1980.

The pairing of the two songs may have been musically motivated, but there is at least one distinct link between them, lyrically, in that both refer to the Dog Star (Sirius). “Sailor” asks “Where’s the Dog Star?” and “Saint” answers “See that Dog Star shinin’.” And both songs feature a narrator who is unsure where he may be going, but seems willing to keep going nonetheless. Is it the same narrator / character in the two songs? Or is in one character in the first, and another in the second? If it’s the same character, what part of his story are we hearing in each song? Do they follow on each other?

It seems appropriate that there are as many unanswered and unanswerable questions contained in the lyrics as are asked or hinted at by the narrator. “Maybe going on a dream.” “Sure don’t know what I’m going for…”

Reason is no help—the line in “Saint,” “Holes in what’s left of my reason” harkens back to “Playing in the Band”: “Some folks trust to reason…” And likewise, the lines echo “Dark Star” (note the pun-like similarity to “Dog Star”) and its lines: “Reason tatters, the forces tear loose from the axis.”

So, forget reason. Just head off and move forward, right? (“I’m gonna go for it for sure,” and “Go on and drift your life away.”)

In live performance, “Sailor” frequently ended with a largely improvised Weir-style rave-up (with Garcia’s guitar lines dancing in and out) that included some strong philosophizing about the difference between “freedom from” and “freedom to.” I’m pretty sure this song introduced me to that concept, and I’ve been grateful for the distinction, which comes in handy, actually, in daily life. You can ask yourself, in any given situation where you are aching to be free, whether it is moving towards something, or away from something, that you are longing for. One is a negative motivation, the other, positive. Not to say that it’s never necessary to get free of something—that freedom from cannot be a positive thing. One article on freedom delineated “freedom from” as corresponding to safety or security, while “freedom to” would be characterized as liberty.

The more I look at the two sets of lyrics, the more correspondences I can pick out. Is it possible that Barlow originally wrote them as a single lyric? The reference to “sirens” in “Saint” (“I can hear the sirens call”) makes us think of Odysseus and his journey as a lost sailor. In fact, maybe that’s a key to the song(s).

In “Sailor,” a line that never made much sense to me is “Ooh, lash the mast.” But if we think about the Odysseus story of his encounter with the sirens, he had his crew lash him to the mast so he would not succumb to their call. (“You can hear her calling…”) Hmmm. Maybe…

I love the musical hooks in both songs. In particular, “Saint” has two very strong ones—the “Holes in what’s left of my reason, holes in the knees of my blues,” and, cheesy though it may be, “Sure don’t know what I’m goin’ for, but I’m gonna go for it for sure.” The manner in which both of these strong hooks emerge from the drifty “rain fallin’ down…” jammy sections only adds to their punch. “Drifting and dreaming,” indeed.

So if you’re on a journey (and who isn’t?), and you find yourself adrift, or pursuing the call of the sirens, and the compass card is spinning around, well, the weather will change eventually. And if you’re still walking, then, hey! You’re sure that you can still dance.


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Joined: Sep 23 2008

The Great thing about a good Dead song is that its always multifaceted and can be applied to so many different life experiences. To me, one brilliant facet of Lost Sailor was that it was a pretty blunt message to Garcia. By 79 the good captain was wandering further into the fog of the neverending Persian dragon tail chase and loosing (had lost) his grip on the wheel of the good ship Dead.

Saint speaks toward hope for a redemption and ultimate triumph at the end of our favorite one eyed sailor's particular journey through that demon fog.

Joined: Jun 5 2007
Horse Feathers (1932)

I was watching the Marx Bros. movie 'Horse Feathers' the other night. Groucho plays Quincy Adams Wagstaff, the dean of Huxley(!) College, Thelma Todd is the college widow, Connie (A 'college widow' is a non-college girl who hangs around with students year after year to associate with the male students.)

...A classic scene... Wagstaff's romantic canoe ride with Connie on a duck pond. He serenades her with a guitar and love song (his version of the film's same love song) as she paddles. A quacking duck that follows the canoe interrupts the end of the song. He insults the duck: "That's a wise quack. You keep your bill out of this. How would you like it if I butted into your affairs and laid an egg?" After singing to her, he throws the guitar overboard. The setting of the scene is a spoof on Theodore Dreiser's An American Tragedy:

Wagstaff: This is the first time I've been out in a canoe since I saw The American Tragedy.
Connie: Oh, you're perfectly safe, Professor, in this boat.
Wagstaff: I don't know. I was going to get a flat bottom but the girl at the boat house didn't have one.
Connie: Well you know, Professor, I could go on like this, drifting and dreaming forever. What a day! Spring in the air.
Wagstaff: Who, me? I should spring in the air and fall in the lake?
Connie: Oh, Professor, you're full of whimsy.
Wagstaff: Can you notice it from there? I'm always that way after I eat radishes.

Joined: Jun 26 2013
I am Grateful to You , Stoltzfus

Thanks for those Kind Words

I am very used to watching people's eyes start to Glaze when I get too excited about these I am loving being able to compare notes here on this Site with other Deadheads.

I think you will love watching "The Life of Pi"
It will stretch your " psychedelic subterranean ocean " Imagnination

Joined: Jan 13 2010
thanks for the posts, share-the-light

gotta see that "lop" movie someday.

Joined: Apr 28 2009
The Tunes of a New Era...

For me, "Lost Sailor" > "Saint Of Circumstance" could've been played at every show after '79 and I would've been happy as a clam. There are VERY FEW bad "LS" > "SOC" and quite a surprising amount of magical ones. Just consult the various postings to see how many diff. shows included someone's "special version" of the pair. Granted, there are a lot of versions. However, in the larger scheme of things, I think the "Sailor" > "Saint" pairing is of critical importance on several fronts. Lyrically, it's simply brilliant and w/out a doubt pokes at that existential angst which resides in many of the greatest DEAD tunes. It's powerful enough to have brought me to tears several times, with "Saint Of Circumstance"'s resolute message of soldiering on, despite any hardship which seems to stand in the way on this journey through life.
The pair also underpins my theory that "Go To Heaven" is a truly magnificent album which is often underappreciated historically as well as aesthetically. For a band which by the late-70's was having difficulty laying down studio tracks which contained the same fire and sparkle as their live counterparts, "Go To Heaven" proved several things. First, that the band could still record a great sounding studio album. In my humble opinion, w/out "Go To Heaven" we may never have been given the gift of "In The Dark". Second, "Go To Heaven" demonstrated that the departure of Keith and Donna Godchaux could be overcome with limited disruption. The addition of Brent Mydland was an absolute homerun for the band at just the right time. With his entry came a gust of creativity & steadily excellent musicianship which would help power the band through some superb years, especially '82.
I believe that "Sailor" > "Saint" was the anchor which allowed "Go To Heaven" to play so well as a studio album. Along w/this magical pair would come the beautiful "Althea", the oh so groovy and jam inviting "Feel Like A Stranger, good times rocker "Alabama Getaway" (which served as a good set opener as well as a platform for some hot Garcia leads), as well as two very well-crafted & sung Brent Mydland tunes "Far From Me" and "Easy To Love You".
All of these tunes armed the DEAD with excellent new live material which served both to introduce Brent to the fans and also to allow a bit of re-crafting, resulting in a "new" DEAD sound which we would come to know & love throughout the 80's and beyond. "Go To Heaven" is a brilliant album which instantly secured a stable footing for the transition from Godchaux to Mydland. It gave us funkified 10+ minute "Feel Like A Stranger" workouts, in addition to the mellow, yet edgy "Althea", and the beautiful Garcia solos which arose from its unique vibe.
And we got "Lost Sailor" and "Saint Of Circumstance". Two tracks which lyrically & musically perfectly depicted where the band seemed to be circa 1979. The future was uncertain as always. A new member had arrived & old friends had departed. Arista records needed to be appeased and the show had to go on. I believe that the reason "Sailor" > "Saint" was so often played and so often performed with so much collective gusto, was simple. The pairing struck a nerve lyrically & musically w/the band. And via their passionate renderings, struck a chord with myself & countless fans who are, or have found themselves lost, floating on a sea of uncertainty. Yet we forge ahead, with the seemingly so bright, yet distant, Dog Star lighting the way...

One Man's picture
Joined: May 17 2011
Musically Speaking

It's an interesting song combo lyrically (although I always wondered if Garcia was embarrassed to be singing that he was going to "go for it, for sure") and I remember loving it well enough during its heyday. Looking back, I'm not as interested. I think it's because this is about the time Weir's music crosses the line from being weird and clever to sort of un-musical. Did he ever write a good song after this? It's a matter of taste, and everyone has their thin line beyond which it just tastes funny to them.

PonchoBill's picture
Joined: Jul 29 2009

Great movie. It never crossed my mind how Lost Sailor and Life of Pi are to speak.

Joined: Jun 26 2013
The Life of PI

Have you Seen the Movie
The Life of Pi?

[Pi is an Irrational AND Transcendental Number
...which I can't figure out so some one please Explain...]

The Movie is a Surrealistic Tale of a Young Man
Adrift in a Life Raft in the Pacific Ocean.
His only Companion is a Hungry Tiger.

This puts an Interesting Spin
on the Saint of Circumstance/Tiger in a Trance Metaphor

He is Vulnerable to the Destructive forces of Nature
when the Gales are Howling
and the Ghost Wind is Blowing

He is also Vulnerable to being the next meal
of the Hungry Tiger

The whole concept of "Freedom From"
and "Freedom To" takes on amazing significance.

"Yes there's a Price for Being Free"

Choosing Freedom from Drowning
leads to a Place of Danger
of being Shredded and Devoured
by the Tiger

Ultimately He Learns How to Coexist
with all the Forces of Nature.

with Trouble Ahead and Trouble Behind
and you know that Notion
....Just Crossed my Mind!

uponscrutiny's picture
Joined: Jan 18 2010
Au Revoir?


Joined: Jun 15 2007
Fabulous Concert Song

"Holes in what's left of my reason
Holes in the knees of my blues..."

One of their truly great breaks and after a bit of metaphysical noodling it was always nice to hear them kick things into high gear with some simple, but solid rock and roll licks. Passenger, Don't Ease Me In, all their Chuck Berry and Rolling Stones covers, and the far-too-rarely-played Bertha (I'd have easily preferred one good Bertha over any twelve Big Rivers) were all good that way too. They had a knack in the way they played rock and roll of making the music roll over in what I can only describe as something like a back-flip wave (of thick air?) with a half twist - usually with an E to A chord change as in Jack Straw: "...we can share the wine...", or Truckin' as it moves from the verse into the chorus.

Wow. It really was something to see and hear.


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