An Underground Film Education at Yale

Back at Yale, Bookman and a classmate started something called the Yale Law School Film Society. He ran it for three years, and it became his introduction to the kind of film history that couldn’t be found in a classroom.

Getting the prints wasn’t always legal. Bookman relied on a collector named Bill Everson, whose apartment was stacked floor to ceiling with 16-millimeter film.

“At that time, you saw movies on 16 millimeter, and they were all kinds of distributors. You could get almost any movie you wanted, except ones that, for copyright reasons, you couldn’t, like the Chaplin films, Animal Crackers, and a number of others. I used to go to his apartment in New York, 118 West 79th Street, floor-to-ceiling, 16-millimeter prints. He would come up on the weekend and bring a bag full of prints, and if I wanted to show something like those films, he’d loan me the prints even though they were illegal to show.”

Bookman used the society to bring in directors that many people had already forgotten, along with rising talents of the era like Miloš Forman and Sam Peckinpah. It was a strange and lucky perch for a law student, and it planted the seed for a career built entirely around recognizing great storytellers.

A Rejection From David Begelman

After Yale, Bookman moved home to Los Angeles, determined to break into the movie business, only to discover that 1972 was a brutal year to try to do so. He got plenty of meetings. Almost none of them led anywhere.

One of those meetings was with David Begelman, then a top agent at CMA, arranged through a connection at William Morris.

“He got me into a meeting with David Begelman. Now I remember going into the office, and this long oak desk, and David Begelman is on the phone with Charlie Joffe, who was then Woody Allen’s manager and producer. And I’m thinking, ‘Man, this is where it all happens.’ And I have an interview with David Begelman, I don’t get a job.”

The job that finally worked out came from a different agency entirely, and it came almost by accident. Bookman remembers the exact date of the interview, because it was the day after he’d learned he passed the bar.

“We’ve only been talking for 20 minutes or so, but you seem to be a fairly intelligent young man. How would you like to start Monday? Now I didn’t say, ‘What’s my job? What’s my compensation?’ I said, ‘What time do you want me?’”

He started that Monday in television packaging, having skipped the mailroom altogether.

From Comic Books to Literary Legends

Bookman’s route to becoming known as the industry’s most trusted “book guy” wasn’t a straight line either. His father once told him a story from his childhood that Bookman himself didn’t remember: in sixth grade, he was obsessed with comic books, and his mother wasn’t thrilled about it.

“My mother was very upset and went to my father and said, ‘You’ve got to do something. Bob’s only reading comic books.’ And my dad said, ‘He’s reading.’”

Years later, working in television packaging at ICM, Bookman told agency head Marvin Josephson that his heart was really in motion pictures, not television. Josephson pointed out a problem. Bookman didn’t have any film clients.

“I’ve given you 100% of my brain and none of my heart because my heart is in motion pictures. I want you to make me an agent in the motion picture department. He said, ‘Well, I have a big problem with that.’ I said, ‘What’s that?’ He said, ‘You don’t have any clients, because in television packaging, we were representing companies.’”

A week later, Josephson came back with an offer that would define Bookman’s entire career: the agency’s literary publications department, and with it, clients like Michael Crichton, Tom Wolfe, and, eventually, a roster that stretched back to Tennessee Williams and Margaret Mitchell’s estate through his new mentors.

What Actually Makes a Book Cinematic

Much of the conversation turns to the craft itself, and Bookman is blunt about a common misconception: great novels rarely make great films.

“Well, first of all, it’s probably not a great book because great books tend to involve things inside the protagonist’s head as opposed to actions that take place outside. And if you look at what you consider a great book that’s been made into a movie, you know, the obvious ones, The Great Gatsby, whatever, they’ve never made great movies. Occasionally, they’ll make a very good movie. So the secret to me is finding a good book that has the potential to make a great movie.”

He breaks his own test down into three parts.

“Does it break down into three acts? Because that’s what movies are. Rarely is a successful movie not three acts. Second thing is, does it have characters who have conflicts? Does it have characters who have problems? And third of all, I always like it, is it taking you somewhere you’ve never been before?”

Bookman has a firm rule about authors adapting their own novels: don’t. There’s one exception he can’t help but marvel at.

“I think the biggest mistake they make when adapting a book is not being able to get away from what the book is and getting the spirit of it as the movie. And I’ll give you the greatest example I can give you from the writer’s side, and I’m still in awe of it, and that’s John Irving and The Cider House Rules.”

Irving wrote the novel, adapted the screenplay himself, and won the Oscar for it. Bookman still isn’t entirely sure how rare that is.

“John won the Oscar for best adapted screenplay, but that isn’t even the point. If you look at that book and you look at the script, well, the decisions he had to make, compressing time, compressing characters, and making what was a great book into a great script. I am just totally…”

Best Adaptations and a Hemingway Wager

Asked to name the best book-to-movie adaptations he’s ever seen, Bookman doesn’t hesitate with his first two picks.

“Well, I would say The Silence of the Lambs was a brilliant adaptation. A Beautiful Mind was a really great adaptation.”

His third choice surprised even Kevin Goetz. To Have and Have Not, adapted from what Ernest Hemingway himself considered his worst book.

“The story is Ernest Hemingway and Howard Hawks used to go hunting together, and one day Howard Hawks said to Ernest Hemingway, ‘You know, I bet I could make a great movie out of your worst book.’ And he said, ‘What’s my worst book?’ He said To Have and Have Not. He said, ‘You know, you’re probably right. I was starving for money, and I wrote it just for the money.’”

Not every memory Bookman shares is about books. As a young law student visiting a Warner Bros. set, he found himself standing near John Wayne, an actor he says he’d been raised not to like.

“You know what John Wayne is doing? He’s looking at the photographs of the family of one of the bottom members of the crew, you know, a gaffer or whatever, and acting like this guy was the only person in the world. It so changed my mind about John Wayne for the rest of my life.”

Originality, AI, and What Comes Next

Toward the end of the conversation, Goetz and Bookman turn to the future of the business, and to a question that’s on a lot of people’s minds right now. Can artificial intelligence replace the kind of instinct Bookman has built his career on?

Bookman doesn’t think so.

He’s also careful about what he means when he talks about originality. It doesn’t mean starting from nothing.

“I agree. But originality can be based on IP. It can’t be based on sequels and remakes of existing IP.”

That belief has carried into his newest venture, a financing partnership called V42, built around producing original films for under ten million dollars.

“There are four of us in the partnership. The goal of our company is to raise money so we can finance and co-finance and then produce ourselves ten million dollars and under films. And we have our first film finished, and it’s been accepted at Toronto.”

From a Berkeley history seminar to a career spent finding the movie hidden inside a manuscript, Bob Bookman’s story is a reminder that the best adaptations, on the page or in a career, rarely follow a straight line. They require someone willing to recognize a good story when they see it, and the judgment to know what it needs to become something else entirely.

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