Celebrating the 20th anniversary of Pollyanna Love Cassandra, here’s the letter I wrote to the wonderful painter - Claire Flint back in 2003. Privy to the deep musings on the title-cut characters of our epic double-project, she provided an absolute masterpiece for our cover.

Hi Claire,

I’m supposed to give you the lowdown on the title, “Pollyanna Loves Cassandra.” Alright, here goes:

“Pollyanna,” the somewhat derogatory nickname for a person who is optimistic to a degree so far beyond realism, that such optimism ceases to be a virtue. Instead, it becomes an indication of either 1) weak intellect, or 2) (more probably) great denial.

I don’t know how “Pollyanna” got this reputation, whoever she was. (Editor’s note: She comes from Eleanor H. Porter’s 1913 children’s novel of the same name.)

“Cassandra,” the Trojan prophetess of doom. Apparently, she had displeased a certain god or goddess who punished her by bestowing upon her the “gift” of prophesy. This “gift” came with a particular catch: No one would believe her. So she gradually acquired a deep, sorrowful alienation from the rest of humanity. Cassandra was present in Troy when the Greeks left their wooden horse outside the city gates. She warned her fellow Trojans about the enemy hiding in the horse’s belly, but they ignored her. So, she retreated back to the temple to wait alone for the Greeks to ambush and lay waste to the city.

I take Cassandra to be some sort of archetype for a personality that is peculiarly intelligent, sensitive, but self-fulfillingly tragic.

So, what does it mean that Pollyanna loves Cassandra? The metaphor applies on different levels and in different aspects of life—some profound, some mundane. But the meanings all branch out from one basic truth: The Light, contrary to conventional wisdom, actually loves the Darkness.

Most people, if they’re honest, are sort of intrigued by the seamier side of life. We’re fascinated by people capable of extending their personalities far beyond the boundaries from which we would never venture forth. (That is why people love to gossip.) We love movies and stories about criminals and sex-fiends. We identify and sympathize with the tortured, doomed souls in Film Noir.

There is also the cliché that good girls fall in love with bad boys.

And everybody is a little bit proud of their own occasional proclivity towards naughtiness and mischief.

And something else: Reflexively, people assume that darker, gloomier people are more intelligent than bright, happy people. For better or for worse, when choosing between the opinion of a status-quo optimist and an angry rebel (all things being equal), most of us suspect that the rebel must be on to something. Even if he or she is totally irrational, the passion is at least impressive.

For a lot of us, especially artists, it seems to take a good deal of effort to be happy, and when we meet someone who has an easy time of happiness, we are suspicious. We think, “there must be something wrong with that happy person.”

And most folks agree that John Lennon, the dark brooding Beatle, was more innovative, deep, and arty than Paul the cute happy Beatle. (Editor’s note: After a lifetime of further consideration, it is now understood that this is complete bullshit.)

There’s also some esoteric new age stuff here. Most cultures, in ritual at least, act out their fascination with dark unpleasant things. Disease, disaster, melancholy, and death. Even evil and violence. (How else can you explain things like World Wrestling Federation?) Just think of all those words in the English language with “vi” as their root. “Vi” means life, and all those words have to do with life force, either bright and exciting or dark and frightening: vital, vicious, vibrant, vile, vivacious, viper, et cetera.

The fact that Pollyanna and Cassandra are both female is convenient. The suggestion of lesbianism augments the metaphor. It underscores the forbidden, secretive nature of the longing, and makes it that much more intense and mysterious.

For artists, Cassandra seems to rule the right side of the brain. Pollyanna functions better at work. She can organize what creative progress has already been made, but it is Cassandra who energizes the overflow of images and words and tunes. And though Cassandra is more intriguing, with admirable mental powers, she is self-absorbed and destructive.

I guess the whole point of doing an album like P. Loves C. is to explore dark, sad and confusing things, but we’re really just having a good ol’ time. (Hence, the opening song is subtitled “Rock and Roll is Supposed to Be Fun,” but most every other song is about something slightly sad.) The album would come off as schizophrenic if it weren’t for the kernel of joy embedded in the vile vicious stuff, or the kernel of foreboding sorrow embedded in the vital vivacious stuff.

In a Ying-Yang symbol, there is a small black circle in the center of the white swirl, and a small black circle in the center of the black swirl.

Well, this is all quite convoluted, and I thought it would be easy to articulate until I actually tried. I hope this helps to steer your ideas. I have trust that your own imagination will take over and kick ass. Take your time. I am thrilled and grateful that you’re putting the finishing touch on this project.

Pollyanna and Cassandra Love Claire Flint