“There has never been a biography made about me for American television because I am on a very black list indeed,” read the handwritten fax before the machine on the other end malfunctioned, rendering the rest of the message an abstract of cartridge ink and toner, as if Gerhard Richter had taken his squeegee to it.

A few weeks earlier, I’d mailed Gore Vidal a pitch for a documentary to be called Gore Vidal: In Search of the Best Man—referencing his 1960 Broadway play about a fictional presidential race—which proposed to follow him as he interviewed each of the real presidential candidates in the 2000 campaign, from his distant cousin Al Gore all the way down the ballot to pacifist-socialist Dave McReynolds.

“Sounds like the title of a rom-com about a gay wedding,” he said when I got him on the phone a few weeks later. Nevertheless, he gave me his blessing to pursue funding for a documentary with a different title and told me that I would never find any executive “suicidal” enough to green-light a project about him, the proud thorn in the side of the republic’s ruling class.

We eventually did find an executive brave enough to say yes—the producer of PBS’s American Masters series—and spent the next year filming in Los Angeles; Washington, D.C.; New York; Rome; and at Gore’s villa, La Rondinaia, on the Amalfi coast. When observers would ask about the cameras tailing him, he would declare, “I’m an American Master now.”

After seeing PBS’s promotional teaser, which included an Arthur Schlesinger Jr. sound bite that Gore very much didn’t like (“He’s a lively, witty mind but very much enslaved by certain prejudices”), he threatened to sue us. (He had yet to watch the full movie.) After I reminded him that he’d signed away that right, he asked me how much it would cost to buy the movie from PBS before it aired, obviously in order to quash it. When I gave him a dollar figure, the line went dead.

It wasn’t the first time Gore Vidal had hung up on me, and it wouldn’t be the last. After he finally got around to watching the film—more than once, I suspect—he left me a less-than-three-second-long voice mail: “Hello, it’s wonderful.” Click.

He was still angry over the Schlesinger sound bite, and another by Norman Mailer (“He’s absolutely without character or moral foundation or even intellectual substance”), but he grudgingly agreed to attend the New York premiere, in May 2003. Suffering from an arthritic knee, which stemmed from his service as a warrant officer on an army freight-supply ship in the gelid Bering Sea during World War Two, and mostly confined to a wheelchair while awaiting surgery, he asked to be wheeled into the Museum of Television & Radio through a side entrance so that no one would see him in his “diminished state.”

He left me a less-than-three-second-long voice mail: “Hello, it’s wonderful.” Click.

After the screening, he ambled up to the stage for the Q&A with the help of his wooden crook cane and proceeded to bring down the house. “The most interesting thing is to watch the aging process,” he began his answer to the first question, about what it was like to watch one’s life unfold on a big screen for an hour and a half. “Could I have been that fat? What went wrong with my chin in that shot? These are the moments when real stars start ringing up [Dr.] Pitanguy in Brazil in the old days and come back with new faces.”

Gore Vidal, Kurt Vonnegut Jr., and Norman Mailer in 2007.

Among his old pals in the audience were Paul Newman and Joanne Woodward, Kurt Vonnegut, and Anne Jackson and Eli Wallach, who, in one of many highlights of the evening, got a hold of the mike to ask Gore, “Do you think President Bush has read any of your books?”

Gore furrowed his brow and twirled his cane a few rotations for dramatic effect. “In a word: no. You can tell by the way he reads speeches that language is very new to him. There’s something primal about him. He seems to have swung down from the trees in Cro-Magnon times.” The audience roared as Gore continued to drill down into the stage with his cane.

A jolly good time was had by all, and all was well between Gore and me. I even got a pat on the back from Paul Newman, who reminded me that I was—up to that point, anyway—the only one of Gore’s biographers to have come out on the other side of the process still on speaking terms with him.

“Gore strikes gold” read the e-mail subject line from one of PBS’s executives after the broadcast premiere, on July 30, 2003, referring to the program’s Nielsen rating, a solid 3.8 million prime-time viewers. The date was precisely three months after President George W. Bush had declared Operation Iraqi Freedom a “Mission Accomplished” and three weeks before a suicide bomber would drive a cement mixer into the U.N.’s headquarters in Baghdad, marking the unofficial kickoff to what Gore would call yet another American “perpetual war for perpetual peace.”

Loss and Love

Just weeks after the broadcast, Howard Austen, Gore’s companion of 53 years, died of brain cancer. I called to offer my condolences. Gore at that point was easily a fifth of his preferred Macallan single-malt scotch into the afternoon—and who could blame him? He joked that Howard had given up the ghost at the other end of the dining-room table in the middle of a dinner party in the middle of one of Gore’s exquisite yarns. I knew this wasn’t true, and he knew that I knew it wasn’t true, but I feigned astonishment anyhow, and he feigned delight at my feigned astonishment.

Vidal, right, with Howard Austen on the balcony of their apartment in Rome in 1974.

The truth was that Howard had died in an armchair in an upstairs bedroom of the Hollywood Hills second home they’d owned since 1977, with Gore and their live-in nurse by Howard’s side. “Although there was no breath for speech,” as Gore later recalled the moment, “he now had a sort of wry wise guy from the Bronx expression on his face which said clearly to me who knew all his expressions, ‘So this is the big fucking deal everyone goes on about.’”

My most vivid memory of Howard was the night he intercepted Gore and me at the front door of La Rondinaia after an epic nightcap at Bar Klingsor, off Ravello’s piazza, where Gore was permitted to fix his own drinks, and those of his guests, to the delight of the bar staff. He was fumbling with the villa’s security system when Howard opened the door, in his red bathrobe, scowling, one hand on his hip, the other clutching a Capri Super Slim cigarette. “Your agent’s on the phone—but I don’t think you should take the call in this state.”

Gore brushed Howard aside and shuffled into his study to pick up the phone. Howard turned to me, barking: “Why’d you let him get so drunk!” Moments later a thunderous cacophony burst from the study. We scurried in to see what had happened—my immediate thought being that I really didn’t want to become known as the infamous biographer who had contributed to the accidental death of his famous subject.

Just weeks after the broadcast, Howard Austen, Gore’s companion of 53 years, died of brain cancer.

Instead of the phone, Gore had grabbed the receiver attached to the fax machine, tripped on the cord, and yanked the whole cursed medieval contraption off the desk, crashing into a bookshelf on his way down. We found him slumped against the wall in a pile of books beside the mortally wounded fax machine. He looked up and grinned. Howard stormed out. I followed him into the kitchen, where he sank into a chair and lit up another Capri.

“Shouldn’t we help him to bed?,” I meekly offered. “Screw him! He can sleep there. It certainly wouldn’t be the first time. You’ll never be able to lift him off the floor anyhow.”

As I tiptoed out, I stuck my head into the study to see if Gore was still alive. There he was, America’s “greatest living man of letters,” as Boston Globe columnist George Frazier had anointed him, soundly snoring on the cold terra-cotta-tile floor in his Harvard varsity letterman jacket—a cherished gift from a friend—head resting on the pile of books.

The next morning, when we arrived for the day’s filming, Gore and Howard were playing backgammon over coffee, as they did most mornings, a few feet from the previous evening’s accident scene, since tidied up by one of the housekeepers as if nothing had ever happened.

We’d been shooting in Ravello for a week or so, interviewing Gore for entire afternoons in the top-floor guest bedroom he called “the Princess Margaret Room,” because that’s where “P.M.,” as he referred to her, stayed on her visits. (She reportedly once said of her loyal friend, “The trouble with Gore is that he wants my sister’s job.”) After each day’s interview, he’d invite us back down to his study, make us cocktails (Macallan on the rocks), light a fire in the grand, ornate tiled fireplace opposite his desk, then regale us with all the stories he wouldn’t tell us on-camera that particular day.

Vidal on the terrace of his villa, La Rondinaia, in Ravello, Italy, in 1974.

One of his fireside chats featured an anecdote about Jack Kennedy, whom Gore had met through Jackie, with whom Gore had shared a stepfather, Hugh Dudley Auchincloss Jr. One of Gore’s earliest memories of Jackie, from 1957, was when she “hitched up her gown and showed the innocent Nini [Gore’s younger half-sister] how to douche post-sex.” In Gore’s telling, Jack liked to have sex in a hot bath, due to his bad back, with the woman on top. In one particular session, Jack was having difficulty reaching orgasm, so he pinned his partner underwater until she was near drowning, at which point, according to Gore, her vagina spasmed, triggering Jack’s release. Howard, skeptical from the get-go, cried, “Oh bullshit, Gore!”

Years after Gore told us this story, Darwin Porter and Danforth Prince’s self-described “Hot, Unauthorized, and Unapologetic” book Jacqueline Kennedy Onassis: A Life Beyond Her Wildest Dreams would include a quote from actress Hedy Lamarr—one of Jack’s many mistresses—describing an encounter with the future president, coincidentally, in a bathtub. “In an impulsive move, he pushed me backward. My head was under water, and I felt I was drowning. This caused a vaginal spasm. But he had his orgasm.”

After a few more drinks, we all stumbled to dinner at one of Gore’s favorite ristorantes, Vittoria. Teasing us over our meager PBS expense account, he insisted on picking up the tab, on the condition that we let him order for us—and that we continue drinking. As usual, Howard held it all together in the role of scout leader and den mother.

Even many of Gore’s closest friends were unaware of the depth of his feelings for Howard until his second memoir, Point to Point Navigation, came out in 2006, three years after Howard’s death. There was resentment: “Even after two ‘successful’ cancer operations, he kept right on smoking and that is how ‘we’ ceased to be we and became ‘I.’” And romantic sentimentality, if ever so slight. Just before Howard went into surgery for a brain tumor in Rome, he asked Gore to kiss him. “I did,” wrote Gore, “on the lips, something we’d not done for fifty years.”

On our trek back from Bar Klingsor, I asked Gore if he truly loved Howard, which I knew was a hazardous query. I waited for him to retaliate with some belittling quip about my romantic naïveté. After all, this was a man who had for decades relentlessly mocked the institution of marriage—including gay marriage—and the notion of romantic love. Instead, after a long pause, he said only, softly, “Yes.”

Ashes to Ashes

After Howard was cremated, Gore asked me how I thought he should go about getting Howard’s ashes from the Hollywood Hills to Washington, D.C.’s Rock Creek Cemetery. “Can’t you just check them in your luggage?,” I asked. “No, no, no, the Homeland people will think it’s bomb material, and I’ll get renditioned to Guantánamo.” I suggested he FedEx the ashes instead. “What if they get lost in the mail?” he wondered.

Ten years earlier, Gore had bought two modest side-by-side plots for himself and Howard, about equidistant between the graves of Jimmie Trimble and the 19th-century historian Henry Adams, or “midway between heart and mind,” as he wrote in Palimpsest, his first memoir. Gore has been called “the Henry Adams of our age,” and director Deborah Dickson and I decided to title our documentary The Education of Gore Vidal, after Adams’s Pulitzer Prize–winning autobiography. Jimmie Trimble was a classmate and friend of Gore’s from St. Albans boarding school in Washington, D.C., who was killed on Iwo Jima at age 19, and many pages of Palimpsest are devoted to him. At one point Gore writes, “Since I don’t really know what other people mean by love, I avoid the word.” Yet just a few lines later he confesses he had been, and may still be, “in love” with Jimmie.

Toward the end of our shoot in Ravello, Gore invited me downstairs to his bedroom—he and Howard slept in separate rooms—to show me a portrait of Jimmie he’d mentioned. I’d envisioned a modest framed photograph of Jimmie on a shelf in a corner of the room. Instead, directly above the head of Gore’s bed hung a nearly life-size painting, of young Jimmie holding a model sailboat.

A Gore Vidal portrait by Francesco Vezzoli at Gagosian Gallery in 2006.

Gore stood silently staring at the painting. I considered asking him a question or two about Jimmie, but he was clearly having a moment. It was the only time I’d felt sadness for him, aside from when Howard died. That what was essentially a teenage fling could inhabit so much of the next 60 years of Gore’s inner life was unsettling, especially since, by all accounts other than Gore’s, Jimmie wasn’t gay and, had he not been killed on Iwo Jima, the love would never have been reciprocated. But, having grown up closeted in a rural state, I also understood how such unrequited infatuations have a way of enduring.

“At the grave site the three young women opened a metal box and removed a triangular plastic bag containing brown ashes, which they placed in a hole that had been dug in the yellowy earth”—this is how Gore described the scene as he, his nephew Burr Steers, and friends Barbara Epstein and Boaty Boatwright laid Howard to eternal rest, a year and a half after his death. “It wasn’t until later we learned that this day had been the sixtieth anniversary of the battle for Iwo Jima.” (No one I’ve asked is quite sure how Howard’s ashes finally made it from the Hollywood Hills to Rock Creek Cemetery.)

Above the head of Gore’s bed hung a nearly life-size painting of young Jimmie holding a model sailboat.

Gore had never expected Howard to go first—despite Howard’s chain-smoking habit—and he certainly never wanted to go last. “Working himself into a lather, he lamented that this wasn’t how it was supposed to be,” recounted his friend Michael Mewshaw in his posthumous warts-and-all book about Gore, Sympathy for the Devil. “He was supposed to die before Howard.” How dare Howard ruin the plan!

One day, after our discussion had taken a particularly morbid turn, I asked Gore what his preferred manner of death was. His reply came instantly. An earthquake would shake La Rondinaia—which means “the swallow’s nest” in Italian—loose from its cliffside perch, dispatching Gore, Howard, and the two cats 1,200 feet down into the Tyrrhenian Sea. “We had been too happy and the gods cannot bear the happiness of mortals,” he concluded in Point to Point.

If two people are “too happy” together, I later asked him, what else could “love” possibly be? He didn’t answer, instead changing the subject to a recent TV appearance.

“Move On and Move Out”

Howard’s absence at the “so-called partners desk” they’d shared for decades was the first harbinger. “In 2003 my ‘partner’ (as the politically correct call it) of fifty-three years—Howard Auster—died and now I work here alone,” Gore wrote 15 months after Howard’s death. “Here? Where? When? Who? We shall let ‘why’ linger a while longer in the wings.” It was an admission that he was essentially unmoored without Howard’s presence.

The next year, recovering from a titanium implant in his left knee and no longer able to walk to the piazza, he decided to put La Rondinaia up for sale. “This was a venture for two people,” he told a New York Times reporter of his decision. “Now there’s only one.” He and Howard had bought the 5,500-square-foot, six-bedroom villa in 1972 for $272,000 and over the years made many upgrades. Gore liked to tell visitors which novel, play, or script had paid for which renovation. His historical novel Lincoln, for instance, paid for the pool and sauna. (On the subject of money, he once advised me, “The only point of making it is so you never have to think about it.”)

Vidal’s villa in Ravello.

After sitting on the market for almost two years, unable to attract a buyer willing to overlook its lack of road access, La Rondinaia eventually sold for $17 million to local hotelier Vincenzo Palumbo, who intended to turn it into a “niche destination” for wealthy travelers, with a museum-shrine dedicated to Gore. “I’m not sentimental,” Gore told the New York Times reporter. “Life flows by, and you flow with it or you don’t. Move on and move out.”

His doctor told him to quit drinking or else face serious health consequences, not the worst of which was liver failure. Gore also had type 2 diabetes, which required daily insulin shots to the hip, and he took beta-blockers for hypertension. For a few months he complied. One could safely call him at six o’clock and expect the crisp wit and lucidity he was known for.

But the boredom of sobriety became unbearable, so he began shopping around for a more sympathetic doctor. He eventually found one, who told him if his liver had made it this long—82 years—it wasn’t likely to quit anytime soon. So back he went to the afternoon Macallans beside the fireplace.

Matt Kapp is the Research and Legal Editor for Air Mail