The baddest of the bad boys, the guy who goes all the way back to before the beginning, has been called many things: the Prince of Darkness, the Tempter, the Bringer of Light. As portrayed in John Milton’s Paradise Lost, he was the most beautiful of the angels before he rebelled. Also the most arrogant. “Better to reign in Hell,” he taunts, “than serve in Heav’n.” Charisma incarnate, he gets all the good lines and almost all the girls. This fallen angel, a primal archetype, is undying: whenever men misbehave we think of him. Robert Lovelace in Clarissa, the Vicomte de Valmont in Les Liaisons Dangereuses, Don Juan in print and in opera, the Willoughbys and Wickhams, wily and wicked, of Jane Austen.

More recently, in real life, fabled Hollywood ladykillers like Jack Nicholson and Warren Beatty come to mind, along with hot tempers Steve McQueen and Sean Connery, and men for whom the word “moderation” is moot—though this is often a consequence of youth, as with Johnny Depp, Sean Penn, and Colin Farrell. Let’s just say there would be very little art without our attractive little devils, and centuries of stories would be boring.

America has always loved its bad boys, but it wasn’t until the movies that we got to revel in them as one nation. Suddenly, in the 1930s, the libertine, gangster, outlaw, scofflaw, public enemy, serial seducer, bank robber, and sexy barn burner had faces. And what faces! James Cagney and Humphrey Bogart as bootleggers, the young Clark Gable as a meanie in black leather (more than once he played dubious characters called “Blackie”), Paul Muni and George Raft as mobsters. Darkness, temptation, light—the black-and-white film of early Hollywood caught it all in deep shadows and gray velvet, compositions of smoke and pearl. And then there was that gleam, which you cannot get in Technicolor, those dangerous gleaming eyes with lashes you can count.

Odd how we so often root for the bad boy, wanting him to succeed, or at least to get away. Why? Because he’s the one with the energy. And though William Shakespeare wrote that “ripeness is all,” energy is everything. It is light and therefore illumination; it is movement and therefore change; it tests the boundaries of freedom.

In those early years of Hollywood, however, bad boys appeared only as characters on-screen. The studios did their best to ensure that the private lives and peccadilloes of its stars stayed within boundaries—they were smoothed over or covered up. Mickey Rooney, for example, playing Andy Hardy in 16 films, became America’s ultimate good boy, cute as a bug’s ear and a real Energizer Bunny. What his fan club did not know was that adorable Mickey Rooney was energetically bedding MGM’s beauties, not to mention the local working girls. The franchise would have been lost if viewers had seen Andy Hardy as an under-age Casanova. So it was a constant cat-and-mouse game with the tabloids and with those two gatekeepers of industry gossip, the syndicated columnists Louella Parsons and Hedda Hopper.

Lo the 1950s, a decade that continues to be decried as uptight and lockstep when in truth it saw a blossoming in literature, theater, and art that was majestic. The decade’s first stirrings actually began a few years earlier, as is often the case with decades. In 1947, on Broadway, a human A-bomb named Marlon Brando was changing the paradigm with his blazingly unbuttoned and exploratory performance as Stanley Kowalski in A Streetcar Named Desire. Yes, the 50s would be the era of gray flannel—a metaphor struck by Sloan Wilson’s best-seller of 1955, The Man in the Gray Flannel Suit—but in September of 1951, when the film of Streetcar, with Brando, was released in movie theaters across the country, it also became the decade of the white T-shirt. An undershirt! (Two months later, in November of 1951, the choreographic genius George Balanchine re-costumed his masterpiece The Four Temperaments, putting the classical men of the New York City Ballet in black tights and distinctly modernist white T-shirts.) With the film The Wild One following in 1953, Brando “branded” that undershirt: it was anti-gray flannel, it was my-way-or-the-highway, it was T for testosterone, it was id. In 1955, a newcomer named James Dean starred in Rebel Without a Cause, his white T-shirt suggesting the idealism that lurked beneath his angry red jacket.