Before there was Carrie Bradshaw and her BFFs of knowing, sexually independent city girls, there was Audrey Hepburn. Or so author Sam Wasson convincingly claims in his work of cinematic and pop culture excavation, Fifth Avenue, 5 A.M.: Audrey Hepburn, Breakfast at Tiffany's, and the Dawn of the Modern Woman. For Wasson (who studied at the USC School of Cinematic Arts), the film adaptation of Truman Capote's transgressive 1958 novel Breakfast at Tiffany's (1961) was a case study for a changing view of women in America.

The perfect storm of creativity, style and cultural sea change, Breakfast at Tiffany's offered Hepburn the chance to abandon her refined princess typecasting, gave director Blake Edwards the ability to prove he could do something beyond light comedy. It garnered composer Henry Mancini and lyricist Johnny Mercer two Academy Awards and Mickey Rooney the condemnation of no less than Akira Kurosawa. But most importantly, Wasson argues, Breakfast at Tiffany's opened up the floodgates for the phenomenon of the independent, idiosyncratic, sexually liberated single girl in the city, precursor to all those contemporary sexy, mouthy babes of Sex and the City. Holly Golightly was the cultural touchstone who begat a score of simpatico chick flicks, and laid the groundwork for Helen Gurley Brown, Cosmopolitan magazine and the founders of Ms. magazine. Ms. cofounder Letty Cottin Pogrebin offers a compelling first-person testimony of just how subversive Holly was for a convention-bound woman of the era, "it blew me away" she says. "Here was this incredibly glamorous, quirky, slightly bizarre woman who wasn't convinced that she had to live with a man. She was a single girl living a life of her own, and she could have an active sex life that wasn't morally questionable. I had never seen that before."

Wasson's slim, elegant book, which takes its title from the first scene in Breakfast at Tiffany's shot on the first day of filming at Tiffany & Co is a peek into the battle strategic machinations of Hollywood in building a movie that at every turn would cause its audience to forget they were watching a movie starring the refined Hepburn as a trollop.

More than a film, Breakfast at Tiffany's was a touchstone that skirted the slowly crumbling bylaws of the Production Code, argues Wasson, and ushered in a very different notion of femininity, outside the ranks of libidinous Jayne Mansfield or goody-two-shoes Doris Day. It was "a notable change in the feminine ideal, from the fifties young lady who matures by falling in love and becoming wifelike, to the early sixties girl who matures by cultivating a fashion sense so unique, it could only be hers and hers alone." Screenwriter George Axelrod struggled mightily to stay true to the spirit of Truman Capote's modern courtesan heroine, while carefully cloaking the script's excesses in the heterosexual romance between Hepburn and George Peppard that gave the film its more conventional aura. At its heart, and easily forgotten in the interim, is the film's essence, a sophisticated, seemingly devil may care prostitute who finances her city life by turning tricks. Casting the chaste, demure Hepburn was, paradox of paradoxes, both a way to distract from how Holly Golightly makes her living, and a glamorous incitement to scores of impressionable young women charmed by Holly's ability to bend the world to her will. Hepburn was initially, understandably, reluctant. As she told producer Marty Jurow "you have a wonderful script, but I can't play a hooker."

As much as a production history, Wasson's book is a powerful testament to the small miracle of how films are made despite endless meddling and resistant personalities, corporate interference and creative small-mindedness. Despite our knowledge that Breakfast at Tiffany's did indeed become a 1961 film, Wasson makes his audience marvel at the many ways the film almost didn't happen, or threatened to appear in far different form than we now know it. Wasson digs deep into the production story behind the film, including Truman Capote's distaste for the movie version. He longed to see Marilyn Monroe in the lead. And during an initial lunch meeting with producer Marty Jurow at the Colony Restaurant on Madison and Sixty-first, Capote had to be talked out of the notion of playing the male lead in the film version. Equally compelling, are details of the elaborately choreographed party scene in Breakfast that early slapstick-fan Blake Edwards staged with the precision timing of a Mack Sennett silent number. Post-production Paramount's Publicity Department scrambled mightily to do its own post-op spin on the sexually free-wheeling Holly Golightly by illustrating her with her onscreen pet "Cat" on her shoulder in the film's poster art. That quirky detail was part of Paramount's positing of Holly as a "kook," "one of many pieces of fifties slang to give nonconformist eccentricity a positive spin."

Wasson's production history is accessorized by the juicy gossip that attended the film. After a screening of George Peppard in Home from the Hill, with producers Jurow and Richard Shepherd, Blake Edwards recounts "I dropped to my knees on the sidewalk to the producers and begged them not to cast him" recalled Edwards, who longed to see Tony Curtis in the Paul Varjak role. But he was overruled. Wasson offers a peek into the dysfunctional Hepburn-Mel Ferrer marriage defined by control, jealousy, Hepburn's routine public humiliation at Ferrer's hands and the miscarriages that devastated the actress. The film signaled the slow exit of legendary costume designer Edith Head, whose services proved secondary to those of French designer Hubert de Givenchy on the Breakfast at Tiffany's set.

Fashion is key to Hepburn's transformation in the public eye from a virginal gamine to a sophisticate and Hollywood's movement forward: her Givenchy wardrobes in several of her films, but most especially in Breakfast illustrated "the subversive power of glamour..." notes Wasson, and "smuggled in some new ideas from the women of the future." Wasson's book not only illustrates how Hollywood of the early Sixties stood on a precipice between the heavily censored films of the past and a boundary-testing cinema ready to engage with a new generation of viewers, but how important style was in finessing that gap. With the help of Givenchy, Holly Golightly ushered in that symbol of big city elegance: the reign of the Little Black Dress.

But for every step forward, there was a step back. Amidst all of Breakfast at Tiffany's progressivism where women were concerned, were remnants of an older, stodgier Hollywood, evident in Mickey Rooney's pre-Borat (2006) turn as Holly's enraged Japanese neighbor Mr. Yunioshi. Producer Richard Shepherd's Creative Management Associates client Akira Kurosawa, for instance, was utterly disgusted by the choice of Rooney. "When he realized that I had been involved with the decision to cast Mickey Rooney as a Japanese man, he almost couldn't talk to me," recalled Shepherd. Prior to Rooney's coming on board, Paramount had staged a phony publicity campaign involving the anticipated arrival of famed Japanese comic Ohayo Arigatou to play the part of Yunioshi, whose arrival in Hollywood was long delayed. "No work yet," "Arigatou" was rumored to say in a collect phone call to Paramount. "Study part. I Methodist actor-Lee Stlassburg Methodist actor. Take time. No hully."

Fifth Avenue, 5 A.M.: Audrey Hepburn, Breakfast at Tiffany's, and the Dawn of the Modern Woman by Sam Wasson, HarperStudio, $19.99, 231 pages.

by Felicia Feaster