Friedman, a man with a problematic singing voice, was, at one time, a prodigious writer of highly personal songs that were often hard to listen to, sung in that difficult voice of his. A central tragedy of the poor devil’s life — to write with sensitivity for an instrument so ill-suited to music. The singer-songwriter had a good sense of pitch, it was not a matter of tone-deafness, in the strict sense. For all his skill on guitar and piano, for all of his original musical ideas, his singing was more than anything a certain lack of grace.

When he was found dead, naked in a chair last summer in his home in Santa Fe, his older brother was contacted by a Medical Examiner. “Just like on TV,” he said. The two brothers flew down to New Mexico to clear his cluttered house and settle his tangled business affairs. They lived for two weeks as guests of Friedman’s ex, a generous woman he finally rejected when he felt she’d been insufficiently supportive when he was inconsolable over the death of his mother, at almost a hundred. “She was his rock,” said his older brother, after their mother died, “he was lost without her.”

The older brother was dogged by guilt, he’d finally had it with his demanding, eternally unhappy youngest brother and had laid into him at one point. The younger brother had never spoken to him again. It had been three years. Then the call from the Medical Examiner asking what to do with the dead body. The middle brother, always a practical man, had avoided a fatal falling out with the youngest by always keeping him at arm’s distance. When an annoying email arrived, screen after screen of tortuous arguments, the middle brother immediately hit delete. He took the same approach to the clutter in the dead brother’s house. Several cartons of contractor bags, a quick look and toss the stuff.

Among the things tossed, to my great regret, were a series of letters between Friedman and the father he always complained didn’t respect him. A box of letters between father and son. They felt like voyeurs after beginning to read them and quickly tossed the collection. As a longtime student of Friedman, and someone who knew his father pretty well too, I feel the loss of these unknown letters keenly. Goddamn, I would have loved to read those letters! There was a book full of pathos and insight in that back and forth, 100%.

Another book, saved by the older brother, exists. It is the hard-covered once blank book where all of the lyrics (and probably the chords) to all of Friedman’s songs were inscribed. The definitive record of a life in music that was almost lived. If only he’d had the voice to sing them. It occurred to me recently to ask the brother if I can borrow this book for a while, to read his collected songs and use them to reconstruct his painful, illuminating life. The endlessly repeating tragedy of his life is the greatest cautionary tale I know.

Many years ago, and I mean decades now, Friedman accused me of using my friends as lab rats in my psychological dissections. I suppose he had a point, the long serving, giant lab rat, though I plead science and the expansion of human knowledge as a redeeming rationale for my experiments (as all the great monsters of history have). We are raised, many of us (and probably all of us who are subject to bouts of misery), deliberately blinded to what we are actually up against in this life. It takes determination, and openess, as well as a certain amount of blind luck, to eventually begin to see the crucial clues that are zealously hidden from us. Friends as lab rats, a small price to pay sometimes, to learn the things we need to learn to live less miserable lives.

(Cold? I don’t know. It certainly doesn’t put the narrator in the most sympathetic light. Start again.)

In telling the story of the talented, miserable, demanding, aggressively unhappy Friedman, I will try to illuminate the two paths open to each of us. We can struggle, in the darkness, to be right, always, to justify, everything, to prevail, at any cost. We can struggle to grasp what is intolerable in our lives, work to see and understand what particularly triggers our misery, seek to suffer less and inflict less pain in the world. I am, clearly, biased toward the second way. Friedman is the greatest example I know, though far from the only one, of the first way — the way of righteous anger and eternal victimhood and fatal disappointment.

Yes, we also have a president now who fits that description– a selfish, childish person who is always the victim, always right to be angry, a fundamentally unhappy person who, although already very wealthy, can never get enough. Forget him, if you can, as I tell you the story of Friedman, the youngest of three boys, an envious sibling who never got enough respect from dad or love from mom.

“OK, let me get this straight, sir,” says nobody in particular “you propose to tell the story of a remorseless, graceless asshole, with no insight into his own misery, told without sympathy, the tale of a putz famous for sweeping others into the ‘putzbin of history’ for betrayals real and imagined.”

I wouldn’t use that as my elevator pitch, no.

“Get on with it, then, why should anybody give a rat’s tutu about this so-called book proposal?”

Insight, man. Hard to come by. Look at it as I pieced it together. At one time this guy was my closest friend. Over the years I came to see, more and more unmistakably, that he was, in elemental ways, an unredeemable version of the worst of my father. Both were smart, articulate, capable of waging fierce arguments to the death, both were supremely sensitive in their own feelings and often monstrously insensitive to the feelings of others. My long wrestling match with Friedman turned out to be an attempt to get a grip on the dilemma with my own father.

“OK, so far you ain’t selling jack, son.”

Says the voice of the internalized victimizer. Look, I’ve been putting together clues for many years now. The Book of Friedman might be the most straightforward way to put them between two covers in the context of a story with a start, middle and end. Much easier to write than draft two of the 1,200 pages I’ve written as I came to see my father’s tragic point of view through his too late clear eyes.

“If you say so…” then there is the pregnant pause, more potent in its power to undermine than any words could be, “we’ll see if this idea comes to anything more than dozens of other big ideas you’ve hatched over the course of the long misadventure that has been your life here, dreamer.”

Which leaves me with this toothache of a thought: What is left of our lives here, beyond what we leave behind?