Unlike the menacing strictures and structures of the previous song, "Cloudy" is airy and breezy. The duo's breathy delivery, punctuated by bell-like chimes and filigrees of guitar, gives the piece a relaxed and open feel.
Our speaker this time is a hitchhiker, one who depends on the whims of random others for transportation. He describes himself as a "ragamuffin"-- a lovable, if poor, creature-- and a "child," innocent and open to new experiences. He has even abandoned his shadow, which disappeared when the Sun did.
He is travelling down the California coast from Berkeley-- that hotbed of social ferment, youthful protest, and radicalism-- to Carmel, a bedroom village of sleepy older folks (later famous for having Clint Eastwood as its mayor). The locations stand for the wide range of the speaker's wandering thoughts.
These thoughts also range from the weighty (and literally heavy) Russian novels of Tolstoy to the beloved children's character Tinkerbell, the flitting fairy from Peter Pan.
The chance to free-associate, to have his thoughts elaborate on themselves and reverberate off of each other, brings a childlike, "fingerpainted" (our third image from childhood) smile to our wanderer, who seems to carry nothing heavier than some photographs. Compare this to the usual negative connotations of clouds, making having a good mood an active endeavor: "Gray skies are gonna clear up/ Put on a happy face" and "When I think of a day that's gray and lonely/ I just pick up my chin and grin and say/ The Sun'll come out tomorrow."
This cloudy reverie, however, is sandwiched between two negative images. The initial reaction to the clouds is sadness: "Sometimes I thing they're hanging down on me."
Then, again, after the imagery of childhood and dreaminess, we see that such freedom is not permanently welcome. The speaker addresses the "sunshine," usually that which dissipates and drives away clouds, and asks it to "bend [his] mind." This somewhat psychedelic image seems to beg for the sunshine to give shape to his thoughts, to force them into some coherence, the way a rainbow's arc neatly lines up its colors.
But the sunshine is not responsive; the clouds "stick to the sky" and refuse to budge. They now present a vague, uneasy doubt, a "floating question why." All they are good for is hanging around until they "die."
The song ends with uncertainty about uncertainty. At the very first, aimlessness was oppressive. Then, suddenly, it presented possibility-- the opportunity for discovery and the pairing of unlikely concepts.
Ultimately, aimlessness reveals itself to be just another word for being lost. The clouds are not in control of their motion, and now neither is he: "They don't know where they're going... neither to do I." (Simon still hadn't found his way later, when he exclaimed in "Me and Julio": "I'm on my way/ Don't know where I'm going/ But I'm on my way.")
In the previous song, the speaker bristles at the preset "patterns" his life is predestined to take. Here, he bemoans his "cloudy" lack of direction and purpose. Either there is "sunshine," which means also having shadows... or "clouds," which means not having any sunshine. There must be a happy medium between being always told where to go and never knowing where to go. But it is not found in the last song, or this.
In "Cloudy," Simon examines both sides of an unstructured life with the image of clouds. It would be another three years before Joni Mitchell wrote her famous verse about "both sides" of clouds.
Next song: Homeward Bound