No country has folklore more deeply invested in the myth of the heroic outsider than the United States, given its revolutionary origins and veneration of the frontier, which, the historian Frederick Jackson Turner famously argued, indelibly shaped Americans’ sense of identity – their prizing of individuality and freedom and independence.

The legends surrounding the frontiersman Daniel Boone (and quite probably Davy Crockett, too) would help inspire Natty Bumppo in James Fenimore Cooper’s Leatherstocking Tales – a loner and “pathfinder,” without parents or a wife or children, who lives on the edge of the frontier, knowing his way of life is doomed by the relentless advance of civilization. The lone gunslinger would also become a familiar trope in movie westerns: most notably in High Noon (1952), where Gary Cooper plays the part of a newly married town marshal who, on the eve of his retirement, must face down a notorious outlaw and his gang – with no deputy or townspeople to provide backup; and Shane (1953), where Alan Ladd plays a mysterious drifter who rides into town and saves a family of homesteaders when an evil cattle baron threatens to run them off their land. At the end of that movie, the family’s young son begs Shane to stay, but he rides off on his horse, saying he doesn’t belong there: “A man has to be what he is . . . A brand sticks.”

These characters embody an old-fashioned frontier ethic as well as Emerson’s credo that “whoso would be a man, must be a nonconformist.” For that matter, a startling number of iconic movie heroes are what Melville’s Ishmael calls “Isolatoes” – “not acknowledging the common continent of men, but each Isolato living on a separate continent of his own.” Cut off by choice or circumstances, those isolatoes include such disparate characters as Rambo, Wolverine, many of the most memorable characters played by Humphrey Bogart (from Rick in Casablanca to Charlie in The African Queen), Dustin Hoffman (in The Graduate, Midnight Cowboy, Rain Man), and Leonardo DiCaprio (as Gatsby, Howard Hughes in The Aviator, and the Man in the Iron Mask); and a growing number of astronauts lost in space in movies like Gravity, Solaris, Moon, and The Martian.

In a 1980 essay, the scholar Richard E Meyer wrote that the American outlaw hero tends to (re)emerge during times of economic or social crisis and is regarded as a “man of the people” who stands in opposition to oppressive political or business interests (yes, the Robin Hood legend again in a new guise). For instance, the legend of Jesse James, who led a gang of train and bank robbers on a crime spree that spanned some seven years, grew during the Reconstruction era in the South, when anger over the defeat of the Confederacy was often directed at symbols of authority – like the banks and trains Jesse James robbed. The pattern was repeated in a similar fashion half a century later, Meyer adds, as “Pretty Boy Floyd, Oklahoma’s outlaw hero of the Great Depression, symbolically strikes back against the bloodsucking forces of absentee ownership every time he hits a bank or a train.”

In Black American folk culture, the trickster hero Brer Rabbit – whose stories can be traced back to Africa and the Caribbean – possesses an outsider’s sympathetic appeal: The resourceful rabbit, who gets the best of more powerful creatures through his cleverness and wit, was an appealing figure for slaves and their descendants coping with oppression and discrimination. And contemporary kin of Brer Rabbit continues to captivate: The effortlessly cool Bugs Bunny, for one, is always ready with the snappy comeback, the winning wisecrack, and he always triumphs over his archenemy, the bumbling, baby-faced Elmer Fudd.

Bugs’s anarchic streak is shared by many American cartoon heroes, from Woody Woodpecker with his maniacal laugh, to the hot-tempered Donald Duck, to the Cat in the Hat, a con artist and small-time chaos monster, dressed in a bow tie and a red-and-white-striped top hat, who disrupts a quiet household, creating havoc and mess.

In the 1950s, some Americans doubled down on their romance with rebels and renegades – partly in reaction to the contrary movement toward conformity, which had accompanied the growth of consumer culture.

The 1950s were the decade that produced that classic novel of teenage alienation The Catcher in the Rye (1951) and movies like The Wild One (1953), Rebel Without a Cause (1955), and Jailhouse Rock (1957) starring a trio of actors – Marlon Brando, James Dean, and Elvis Presley – whose brooding intensity and bad- boy cool created a new template of pop culture stardom.

This was the decade in which Beat writers published their most influential work: Allen Ginsberg’s Howl in 1956, Jack Kerouac’s On the Road in 1957, and William S Burroughs’s Naked Lunch in 1959 – daring, provocative works whose experimental techniques and explicit content outraged the “square” world but energised the arts scene and laid the groundwork for what became the counterculture in the 1960s.

Existentialism – and talk of “the absurd” – circulated on college campuses, people spoke about growing up under the shadow of the atomic bomb, and books like David Riesman’s The Lonely Crowd (1950) and William H Whyte’s Organization Man (1956) became bestsellers. Those books addressed the countertrend in the 1950s of increased uniformity as more and more people became office workers and moved to the suburbs and a new world of corporate bureaucracy threatened to trample the old maverick virtues of individualism and independence.

Whyte’s book – much like Sloan Wilson’s popular 1955 novel, The Man in the Gray Flannel Suit – argued that the kind of get-along groupthink that often prevailed in big offices suppressed creativity and entrepreneurship. And Riesman’s popular but sometimes misunderstood book (written with Nathan Glazer and Reuel Denney) argued that with the decline of tradition-directed societies in the late Middle Ages two main character types had evolved: the “inner-directed” type, who relies upon an inner gyroscope (largely forged by early or parental values) to navigate life; and the “other-directed” type, who is sensitive “to the expectations and preferences of others.”

Riesman saw the perils of the “other-directed” personality type becoming more dominant in the mid-20th century (think what he would have made of social media users obsessed with racking up “likes”), but he also saw how individuals who were purely “inner-directed” could lapse into blinkered or egotistical behaviour (remember: Ahab was an isolato, too). Therefore, the aim of a truly autonomous person, he suggested, was to somehow achieve a balance between pragmatism and independence, empathy and detachment.

As America moved into the 1960s, divisions widened between outsiders and the so-called silent majority – divisions over Vietnam and the civil rights movement, and over everything from music to fashion to living arrangements. Rock ’n’ roll and psychedelia and drugs were all components of the counterculture revolt against conformity, and in his 1970 book, The Greening of America, Yale professor Charles Reich heralded this development as the momentous advent of what he called “Consciousness III.” He fatuously suggested that the hippies’ lifestyle rebellion would bring about a moral and ideological revolution, as though wearing bell bottoms and love beads would somehow magically lead to a change in the political order. Instead, their tie-dyed trappings of revolt were quickly co-opted by Madison Avenue. Outsiders – be it Holden Caulfield in The Catcher in the Rye or Dustin Hoff man’s character Benjamin in The Graduate or the brooding heroes of French existential novels – had already made alienation and rebellion fashionable among the college crowd; now the counterculture could be commodified for the masses.

Excerpted with permission from The Great Wave: The Era of Radical Disruption and the Rise of the Outsider, Michiko Kakutani, William Collins.