Libby Holman's life was one of early poverty, extraordinary talent, scandal, fabulous wealth and tragedy. She's the stuff books and movies are ripe for. Born into a once-prosperous Jewish family in Ohio, her family's stock brokerage business collapsed in 1904 when her uncle disappeared after embezzling nearly $1 million, leaving her innocent father scandalized and bankrupt. Her mother raised her three daughters in anger over their loss of wealth and position, undoubtedly affecting Libby's ambitious nature.

Primarily known today as a Broadway actress and torch singer of the 1920s-30s, Libby got her start in the theater by touring in "The Fool." The author of the play, Channing Pollock, recognized her talent and advised her to drop out of college and pursue a theatrical career. Joining the Theatre Guild, in 1925 she appeared in the chorus of "The Garrick Gaieties" before gaining notice in "The Greenwich Village Follies" the following year. She continued to appear in "Merry-Go-Round" (1927), "Rainbow," (1928) and "Ned Wayburn's Gambols" (1929). Libby appeared with Clifton Webb in "The Little Show" (a big 1929 hit; Libby singing "Moanin' Low", becoming one of her earliest trademark songs) and "Three's A Crowd" (1930; Libby introducing the standard, "Body and Soul"), which made them both top-ranked musical stars. Her early breakthrough successes would result from her associations with Howard Dietz, one of her greatest benefactors, and Clifton Webb, who complimented her on stage. She and Webb remained longtime friends but ultimately had a falling out of sorts after 1938.

Libby was exceedingly complex. Bisexual, she preferred the company of gay men, but two of the three most significant intimate relationships of her life were with avowed lesbians, the equally fascinating unconventional DuPont heiress Louisa d'Andelot Carpenter Jenny (from 1929) and later, with writer Jane Auer Bowles (from the mid-1940s). However, she periodically sought out men (often sexually conflicted, as with her third most important relationship, actor Montgomery Clift) invariably far younger than herself, only to summarily cast them aside on the basis of some seemingly insignificant slight. She was a fascinating confluence of allure, talent and vanity, masked with a droll sarcastic wit capable of rivaling that of society columnist Lucius Beebe, Robert Benchley, Dorothy Parker or Noël Coward, all of whom were in her social circle. Although she wasn't conventionally beautiful, audiences were drawn to her by her voice and stunning figure (she reputedly invented the strapless evening gown, it becoming one of her trademarks). She could have easily succeeded in Hollywood after the advent of talkies, but was decidedly "East Coast", sharing her clique's snobbish disdain for film (although many of them would eventually relent and go on to gain immortality in Hollywood) and harboring some inner insecurity over her looks. To a large degree, however, Libby thrived on the immediate rewards of a live audience, which she could wrap around her little finger with any one of her sexually charged smoky torch songs.

One smitten fan was tobacco heir Zachary "Smith" Reynolds, who caught her act on a lark and spent a fortune following her around the world. As the youngest son of tobacco magnate R.J. Reynolds, the 20-year-old playboy was the real-life "Roaring '20s" manifestation of a character, drawn straight from an F. Scott Fitzgerald novel. He had complete disinterest in the family business, an inexhaustible allowance and a volatile temper. Smith, whose one real accomplishment was learning how to fly, also owned a plane, and he literally stalked Libby with it. He wore the 27-year-old singer down and, encouraged by Louisa (herself briefly married) who saw him as a convenient veil of wealth and propriety, Libby married him in 1931. Their marriage was a clash of wills, however; Smith wanted her to leave Broadway and she had no intention of doing so. They agreed on a one-year sabbatical at the family's vast North Carolina estate, Reynolda. Libby, who was born into poverty had always aspired to be wealthy, quickly grew tired of the kind of idle life expected of her. She invited a stream of her flamboyant theatrical friends to the estate and they clashed headlong with the conservative Reynolds family. There were accusations of lesbianism and hedonism that her in-laws could barely stomach. In 1932, over the family's annual alcohol-fueled July 4th holiday party held at the estate, she told her husband she was pregnant and there was reportedly a tense confrontation - stories differ, but there was a gunshot and Libby and Ab Walker (whispered to be her lover), a close friend of Smith's, were indicted for murder. Fearing scandal over their son's activities, the intensely secretive Reynolds family persuaded local authorities to drop the charges; the death was ruled a suicide. The scandal stuck to Libby and her career suffered. Her son Christopher (or "Topper", as she called him) received a large inheritance and Libby received a sizable maintenance agreement that left her independently wealthy for the rest of her life. After the Reynolds debacle was legally settled, Libby and her son went to live with Louisa (who herself had adopted a daughter) and the couple lived openly throughout the remainder of the 1930s in what was then called a "Boston Marriage" in local gossip. Their relationship eventually changed, but Louisa would remain a lifelong friend and confidant. Libby also continued to pursue a Broadway career, with ever-diminishing returns. Despite her undeniable talent, she was keenly aware that producers hired her in hopes that her scandalized personal life would increase the box office. One of her most ardent supporters during this period was the unabashedly gay Herald-Tribune columnist Lucius Beebe, who never missed an opportunity to document her moves within New York's café society, always portraying her in the best possible light. His support of her came as a welcome relief during this first dark period of her career, although she certainly didn't need the money.

From the early to mid-'30s she gained dramatic experience in 'Jasper Deeter''s Hedgerow Theatre and returned to Broadway in "Revenge With Music," (1934; singing "You and the Night and Music") along with performing in nightclubs in New York and London. Despite her excellent performances, the Reynolds scandal dogged her and she was often hissed and booed. She received star billing (singing the title song as Mme. Baltin/Jeanne Montaigne) in the 1938 Cole Porter musical flop, "You Never Know" with Clifton Webb, Lupe Velez (whom she despised) and Toby Wing. Not content to live the life of the typical millionaire grand dame, she became a yoga enthusiast and financed experimental theater (1942's "Mexican Mural" starring one of her obsessions, Montgomery Clift, who would become a lifelong friend and infrequent lover), continued to sing and record smoky torch songs. She traveled extensively and was unhappily married two more times (her second husband, sometime-actor Ralph Holmes or "Rafe" to his friends, committed suicide shortly after returning from duty in WW II; her third husband survived her) and adopted two sons. In the mid-40s she met writer Jane Auer Bowles and their attraction was immediate. The unconventionally married writer, married openly homosexual author Paul Bowles ("The Sheltering Sky"), shared Libby's disdain for their common Jewish heritage -- another one of Libby's psychological quirks -- and, as in the case of Louisa, lived together openly. Enamored by the blues, she caused a stir in the 1940s nightclub scene by touring with famed black guitarist Josh White (ironic, given her sexual ambivalence toward men in general). Together they appeared in her sole IMDB film credit, the experimental and aptly-yet-coincidentally named, Dreams That Money Can Buy (1947) in 1947.

Tragically, her son died with a friend climbing California's Mt. Whitney in 1950. She channeled her grief into a foundation dedicated to promoting racial understanding and equality. She continued to record and perform in a one-woman show, "Blues, Ballads and Sin Songs" with pianist Gerald Cook into the 1950s. Although she could still belt out a tune, her later renditions of her standards were seldom recorded and are not generally well known today, having been banned on the radio for decades due to their sexual overtones. She fell into a deep depression in 1957 and broke out of it by taking courses in Zen Buddhism at the New School, and through a mutual friend met an art teacher and sculptor, Louis Schanker. The two met infrequently over the next few weeks before seeing each other on a regular basis. Whatever attracted Libby to him eluded her friends. Schanker was older than Libby--uncharacteristically for her--and, despite having a reputation as an important abstract expressionist, he was unworldly, inarticulate and not exactly handsome. In fact, during most of their courtship he was living with a much younger woman. For her part, Libby seemed to be living in fear that this was her last chance at love, and sought someone to anchor her life; companionship, on her terms. His entry into wealth by marriage stifled whatever artistic ambitions he possessed. His standing in the art world quickly evaporated, he increasingly drank and clashed with her teenage sons. It was an unhappy marriage, but one that would take. The 1960s were marked by Schanker's banishment of most of her old friends (like her previous husbands, he banned homosexuals from their homes and was intensely jealous of anyone she ever slept with, male or female), Jane Bowles' debilitating stroke and the assassination of Dr. Martin Luther King, whom she and her foundation actively supported, affected her deeply. Increasingly emotionally isolated from her friends and depressed, Libby sank into alcoholism after 1968. Sadly, she herself committed suicide in June, 1971, found slumped over in her Rolls-Royce at her Connecticut mansion. Coretta Scott King attended her funeral. Jane Bowles, blind and schizophrenic, died in a sanitarium in 1973 and Louisa was killed flying her private plane on February 8, 1976.