A few months after Esquire published my profile of Bob Rafelson, I received an e-mail from the retired director informing me that he was taking his two younger sons to Puerto Rico for what he described as a “last hurrah.”

It was July 2019, and Bob was 86 years old with a steel rod in his spine, another in one of his arms, two shoulders that needed replacing, and other ailments acquired during a life that had been lived anything but carefully. But I still had a hard time believing that this would be the “last” of anything for the innovative, irascible, larger-than-life filmmaker. A “hurrah” of some kind, for sure, but certainly not his last, because Bob was a man who seemed like he’d probably live forever, just to be contrary.

What I had no trouble believing, however, was the next e-mail I received from Bob, this one from Puerto Rico, with a photo of Bob amidst the nearly 500,000 who’d gathered in the streets of San Juan to demand the resignation of Governor Ricardo Rosselló, whose administration had scandalized public opinion by offensive comments and threats Rosselló had made in a group chat on Telegram.

Rafelson and Nicholson at the actor’s house in 1969.

In what can only be described as a Rafelsonian turn of events, Bob’s hotel was across the street from the governor’s mansion, giving him a direct view of the kind of action he so frequently found himself in the middle of—whether he was being thrown from a bull to win a $5 bet; springing Dennis Hopper from a mental hospital; or chancing upon a popular uprising in India, where he broke both arms. For most of us this would have been extraordinary. For Bob it was just another revolution.

The Esquire profile opens with an e-mail he had sent to the editors of the magazine Sight & Sound, who had erroneously declared him “gone.” Bob did not want a retraction—just a free subscription. “There are several people who have heard the rumors of my death that I owed money to so I suppose I should be grateful,” he wrote.

Micky Dolenz, of the Monkees, with Rafelson, who created the made-for-TV band.

“On the other hand this subterfuge could backfire. Many years back I prized my anonymity to an absurd degree. An Italian extra who spoke perfect English seduced [Marcello] Mastroianni, [Catherine] Deneuve and others into doing a movie with him pretending to be me. He raised more money than I was customarily paid.”

Last month, I received an e-mail from Rafelson’s wife, Gaby, letting me know that Bob had died peacefully the night before. This time Bob was gone for real, at the age of 89. To say that he lived the hell out of those 89 years would be a colossal understatement.

Described by Francis Ford Coppola as “one of the most important cinematic artists of his era,” Bob initially bounced from job to job in Hollywood, never quite finding himself able to get comfortable with authority. As if to emphasize that point, he once trashed the office of MCA head Lew Wasserman, then the most feared and powerful man in show business. “We weren’t on the same page” is how Bob summarized the event when I spent three days interviewing him at the 1950s cabin in Aspen where he’d lived full-time after leaving Hollywood and the film industry in 2003.

Bob was a man who seemed like he’d probably live forever, just to be contrary.

Rafelson’s rise in Hollywood began in the mid-1960s with the creation of the made-for-TV band the Monkees. When their series became a hit, it gave Bob and his partner, Bert Schneider, the money to bankroll Easy Rider. With Steve Blauner, they formed BBS, the seminal New Hollywood production company that green-lighted The Last Picture Show, Hearts and Minds, and Rafelson’s own Five Easy Pieces, the film that turned his friend Jack Nicholson into a full-fledged movie star. “I may have thought I started his career,” Nicholson told me. “But I think he started mine.”

With a keen eye for talent, Bob gave Arnold Schwarzenegger his first serious film role; resurrected Jessica Lange’s career, after a disastrous King Kong remake; and reassured an uneasy Schneider about Peter Bogdanovich’s ability to execute The Last Picture Show. And though he was one of the key architects of the New Hollywood of the late 1960s and early 1970s—a case can be made that the New Hollywood doesn’t happen without Rafelson—he was also a Huston-esque throwback and one of the last filmmakers to turn daily life on and off the set into the stuff of adventure.

Rafelson (right) with Nicholson and Jessica Lange at the Cannes Film Festival for The Postman Always Rings Twice, 1981.

During a nearly 40-year career, Bob directed 10 meticulous films (five starring Nicholson), including The Postman Always Rings Twice, Black Widow, and Mountains of the Moon, a 1990 historical epic about the relationship between the British explorers Richard Burton and John Speke, which was Bob’s favorite of them all. While making that film, Rafelson convinced a pilot that a stoned actor knew how to fly a plane.

Our marathon interview sessions started at midafternoon and took place in Rafelson’s home office, from which he pointed outside to show me where a neighbor was trying to build a ski lodge that would spoil his view of the mountains. The charming, mercurial filmmaker was unfailingly honest, occasionally intimidating, and not infrequently hilarious.

Nicholson in Five Easy Pieces.

During the three years between the publication of the profile and Rafelson’s death, he and I kept in contact, e-mailing each other about politics, sports (“fuck Duke,” he signed off more than one e-mail during March Madness), and the possibility of co-writing his memoir. But my favorite e-mail from Bob came while I was working on the article and sent him a list of questions about his reputation as a brawler who found trouble wherever he went. Rafelson responded as follows:

It was reported in an English paper that when Bert [Schneider] was on the Academy Awards receiving best documentary [for the Vietnam documentary “Hearts and Minds”] and talking about the Vietnam reps at the Paris Peace Talks that he was cut off by Bob Hope And I got into a fistfight with Frank Sinatra.

I wasn’t even there.

But I have been imprisoned [and] tortured a few times on four different continents. Maybe three. Who counts? I was first jailed at nineteen, I think, for an editorial in the Dartmouth Quarterly about mistreatment of Eskimos. I didn’t write it. I was an editor and went to communist meetings—at which I dozed.

Rafelson on the set of Black Widow, 1987.

The last time [I had] a fight … [was] in the country of Georgia where a policeman blocked my entry into my hotel. There was a whole demonstration outside. He misused a night stick [on me] and I relieved him of it and hit him in the nuts.

Being suspended from the ceiling, feet tied to a roof, in Colombia was painful not so much because of the radio wires attached to my nuts, but because Perry Como was on the radio.

Then there was Mombasa …

With Bob, there was always Mombasa.

Josh Karp is the author of Orson Welles’s Last Movie: The Making of The Other Side of the Wind