On the eve of the much-anticipated release of director Ron Howard’s blockbuster movie, In the Heart of the Sea , I wonder what modern sensibilities will shape this latest retelling of the legend of Moby Dick. We’ve come a long way since John Huston’s 1956 classic film, which involved real live whalers harpooning real live animals off the coast of Portugal, and we can be sure that no whales were harmed during the making of this particular feature. But what is it about whales that draws us to them, that captures the imagination?

Encountering a whale — a real, live cetacean — provokes an almost inescapably metaphysical reaction. It inspires “wonderment,” according to Rebecca Giggs writing of her close encounter with a beached juvenile humpback on the Western Australian coastline, “a dilation of the ordinary.” When a Northern Bottlenose whale swam up the Thames in January 2006, Richard Sabin, collections manager at the Natural History Museum, was called to the scene. “The thing that really took people by surprise,” he explains, “was they were seeing this animal in the middle of London. It’s like the wild swims to you. In the middle of your day job.”

I had assiduously avoided reading Moby Dick until well into my 30s, having believed (wrongly) that it was a paean to whaling and the industrial butchery of these gentle, social, intelligent creatures of the deep. It was only when I read Melville’s extraordinary tome that I realised it was not that at all, and I began to think about the encounter between whale and human for what it tells us about ourselves and our place in the natural world. Moby Dick became for me not a vile and misguided rant, but one of my favourite novels of all time: my desert island book, in fact.

Separated by 161 years and at a fraction of its length, Kathleen Jamie’s Sightlines comes a close second. In a series of 14 loosely connected essays, she travels to uninhabited Scottish islands, is bathed in the aurora borealis off the coast of Greenland, and even explores the inside of human arteries and cells to discover what happens when the human world intersects with that of the natural, the wild. Her encounters with whales — living and long-dead — hold the narrative together like a series of bright golden stitches: sighting a pod of orca circling the remote island of Rona off the north coast of Scotland, cleaning a Blue whale’s bones in the whale hall of the Natural History Museum in Bergen, Norway, discovering a whale’s ear drum washed up on the shore. But it is far from the sea, deep inside a mountain in La Cueva de la Pileta, in Málaga, Spain, that she gets to the heart of the matter.

The chance discovery of Neolithic paintings here in 1905 caused a sensation. Further explorations revealed markings that may date back 20,000 years to Paleolithic times when “there were no wild animals, because every animal was wild; and humans were few.” “But why the animals should appear in deep caves, we don’t know. Hallucinations, maybe. Shaman work. Perhaps people were drawing, in the other sense. Coaxing animal presence out of the deep source, the cave-uterus. We are deep in metaphor, the membranes between body and stone, and cave and animal are dissolved: melded like the two turning bulls.”

It would seem that humans have been representing things since what we like to call the dawn of time itself. Perhaps that is the defining characteristic of our species: “We can say look, that shadow is like an antler, this line suggests an ibex horn, that girl is a deer, this problem is like that; therefore, that solution might just do the trick. The connective leaps, the careful taxonomies, how our minds work.”

The great white whale pursued by Captain Ahab and the hapless crew of the Pequod is, of course, the biggest metaphor of all. To question the reality, the fleshiness, of such a creature — in its sheer power, its heft and size — seems insane, really, and yet like those gawping commuters watching the London whale flounder beneath Battersea Bridge we cannot help but feel that it is a hallucination. There’s something not real, but vividly sur-real, about encountering a whale. “Very like a whale,” is perhaps as near as we can get.

You couldn’t get more real than Philip Hoare’s encounter with a full-grown female sperm whale while diving off the coast of the Azores. The author of Leviathan, or The Whale , was acutely aware that sperm whales are the only animals which can, and indeed have, swallowed humans. But this grand matriarch does not swallow him. Rather, she scans him with a series of powerful sonar clicks, “creating a kind of three-dimensional picture, a sound picture, of me in its head,” and then cruises by, scrutinising him with one enormous eye. “It was the most extraordinary moment of my life,” he recalls. “It was reading me, trying to describe me. Which was kind of ironic. As a writer, I’d spent fifteen years trying to describe a whale, and here was a whale trying to work out what I was.”

We’ll never know what the whale worked out about this skinny finless mammal floundering in her sea. After centuries of industrial whaling, an “animal holocaust” as Hoare calls it that has accounted for over three million whales butchered for their blubber, baleen, bones and ambergris, the one thought she should have had is the one she almost certainly didn’t: here be monsters.