Before we analyze this song, it is important to note the many allusions in it to other Simon songs:
The image in "Can't Run But" of a couple dancing return thus:
"Effortless music from the Cameroons
The spinning darkness of her hair"
while the "pencil-point/love bite" stab in the "shoulder blade" from that song is here softened to:
"...a love/ Who falls against you gently as/ A pickpocket brushes your thigh"
The "Dangling Conversation" reappears here as:
"A conversation... going nowhere"
The opening line to "Call Me Al" is now rendered:
"Sometimes I’ll be walking down/ The street and I’ll be thinking/ Am I crazy"
And the man who, in "Boy in the Bubble," said "Don't cry, Baby, don't cry" now tells the listener to:
"Take it up with the great deceiver/ Who looks you in the eye/ Says, Baby, don’t cry."
Lastly, a plant that we just encountered in "The Coast" returns, namely "The Rose of Jericho."
That taken care of, we can now turn to the song itself and consider it on its own merits. The song seems to be about desire and the many ways and reasons it can go unfulfilled. There is always, it seems, "further to fly" in order to reach such goals. (Also, the breathy alliteration of this phrase sounds a bit like feathery wings.)
The first verse returns to one one Simon's major themes: weariness. One reason desires remain unfilled is simple exhaustion. Some dreams seem to take so long to become realized that the dreams themselves seem to beg for euthanasia-- "Give me up already!" they moan.
But maybe, you will find a love... only it will present itself so gently you will miss it. It will breeze by and be gone before you even realize you should have tried to catch it, and like a "pickpocket" victim, you won't understand until later what you have lost.
There will be sweet "music", yes, and the hypnotic "swirl" of her hair in the "crowded room,"-- perhaps a bar, dance floor, or reception hall. But the "conversation" will frustrate and "go nowhere." (The Cameroons, today simply called "Cameroon," is a West African nation).
"Desire," the speaker insists, is insatiable, like an "open palm" that holds nothing, but keeps needing to be filled. It "wants everything," because it is always empty.
The futility of endless wanting ends up feeling like either madness-- "I’ll be thinking: 'Am I crazy?'"-- or some sort of cosmic sarcasm-- "'Is this some morbid little lie?'"
Desire is not only for things yet to be gotten, but for things once had and now lost. The next lines seem like a description of dementia or Alzheimer's disease: "A recent loss of memory/ A shadow in the family." The "shadow" is both the genetic reality of the illness in the whole "family," and the almost literal sense of "absence"-- the person is absent because he or she does not even remember being part of the family. The specific memory itself is also in "shadow," as it can no longer be seen clearly.
"The baby waves bye-bye" can mean several things. (This is clearly "baby" in the age sense, not "Baby" in the romantic one; all sources agree the word is not capitalized.) One is that childhood is lost as one matures; the "baby" is one's own infancy. Another is that one's children grow up and leave; to us parents, they are still our babies. Sticking with the Alzheimer's idea, whole family members can leave the awareness of the victims and fade into forgotten-ness and "shadow," another sort of farewell. Or perhaps, the Alzheimer's patient is the baby, since he is as helpless as one.
As for the speaker, he pleads, "I’m trying." If there is "further to fly," well, he's "flying" as hard as he can, and has not given up.
Knowing that things lost are desired, the speaker bemoans the idea that he might lose the things he still has, from his relationships to his sensibility. The image is of "falling backward" into a soft-yet-smothering blackness, a "velvet night."
The "open palm" now wants contradictory things (well, "everything" would presumably include opposites). It wants "soil as soft as summer"-- an easy life, in which no effort is required to flourish. It also wants "the strength to push like spring." Few things push as strongly as excited new growth; roots and shoots break stone and cement, and "spring" itself pushes away the drifts and floes of seemingly intractable, implacable winter. So the "palm of desire" wants strength, but the luxury to grow without it. No wonder it is never satisfied!
"A broken laugh," is a rueful thing, but "a broken fever" usually is a hopeful one, as in "I hope her fever breaks soon." For it to be another disappointment, this would have to be the "fever" of the type Peggy Lee sings.
And this is when the speaker calls the "Boy in the Bubble" speaker on his reassurances. Only a "great deceiver" would say "Baby, don’t cry." There is always a reason to cry, and something lost or not attained worth crying over. (It seems this is the "Baby" of the other song, since it is capitalized, but it would be wrong not to explore the possibility of it being the baby mentioned earlier in this song.)
"The Rose of Jericho," again, is a plant that may seem dead, yet can be revived. This may symbolize the endlessly regenerating nature of desire.
The last line, however, seems to finally express what is truly desired-- the ability to fulfill the desires of others, even if that means one's own desire is thereby unfulfilled: "The strength to let you go." It would be weak indeed to give in to one's own selfishness at the expense of the needs of another soul.
The song, in short, starts with the second line of the Serenity Prayer-- "the courage to change the things I can" and ends with the first: "the serenity to accept the things I cannot change." Except this time, it's never going to be "serene" once his love is gone, which she eventually she will be, no matter what. And for that, he's going to need the "strength" to continue to "fly further" toward the ever-retreating horizon of contentment.
In a way, this song is a more mature version of "The Impossible Dream" from "Man of La Mancha," and a more jaded version of Keats' "Ode on a Grecian Urn":
"Bold Lover, never, never canst thou kiss,
Though winning near the goal – yet, do not grieve;
She cannot fade, though thou hast not thy bliss,
For ever wilt thou love, and she be fair!"
For Keats, having "further to fly" means always having a reason to fly, and isn't flying fun? For Simon, flying is exhausting, never reaching the goal is frustrating, and knowing that he will lose his love in the end no matter what is devastating.
He is "tired," the conversation goes "nowhere," and the whole thing might be insanity or a "morbid lie" of Fate. Yet, he flies... and hopes for, at the end, the strength to stop.
The flugelhorn here is played by Hugh Masekela, one of Africa's greatest jazz players. He had an instrumental horn hit in the US-- right around the time of Herb Alpert and Chuck Mangione-- called "Grazin' in the Grass" (1968), which went to #1 and went multi-platinum. Masekela later played on some Byrds cuts. He had left Africa in 1960, following a massacre of unarmed protestors. Years later, Masekela joined Simon onstage at his Graceland concert in Africa.
The trumpeter is Randy Brecker, with a long list of sessions with greats from Springsteen to Mingus. He is Michael's brother, they have recorded as a duo.
The notes that sound like a wood flute are Michael Brecker's EWI.
(There is another error in the liner notes. The guitar is not played by "Ringo Star" and this is not a misprint of the Beatles' drummer's name. It's actually an understandable misprint of the name "Rigo Star.")
The song was covered by folk songbird Holly Near.
Next song: She Moves On