[citation needed] In 1904, the wealthy family grew destitute after Holman's uncle Ross Holzman embezzled nearly $1 million of their stock brokerage business.

She later remembered Holman: "Every afternoon she would arrive after her classes, carrying her schoolbooks, wearing the short skirts, oxfords and beret that were the thing among coeds, and settle down to work..." She was "pleasant, smiling, and matter-of-fact about her method of earning a living, and no matter what amount of money was offered her after her deadline of eleven o'clock [the curfew of the YWCA], her answer was always 'No.

Channing Pollock, the writer of The Fool, recognized Holman's talents immediately and advised her to pursue a theatrical career.

Producer Leonard Sillman relates, in his autobiography Here Lies Leonard Sillman: Straightened Out at Last, that he "liked the name Libby much better than her legal one and under my gentle prodding, 24 hours a day, she changed it.”[7] An early stage colleague who became a longtime close friend was future film star Clifton Webb, then a dancer.

Her big break came while she was appearing with Clifton Webb and Fred Allen in the 1929 Broadway revue The Little Show, in which she first sang the blues number "Moanin' Low" by Ralph Rainger, which earned her a dozen curtain calls on opening night, drew raves from the critics and became her signature song.

[9] The following year, Holman introduced the Howard Dietz and Arthur Schwartz standard "Something to Remember You By" in the show Three's a Crowd, which also starred Allen and Webb.

[10] Other Broadway appearances included The Garrick Gaieties (1925), Merry-Go-Round (1927), Rainbow (1928), Ned Wayburn's Gambols (1929), Revenge with Music (1934), You Never Know (1938, score by Cole Porter), during which production she had a strong rivalry with the Mexican actress Lupe Vélez;[11] and her self-produced one-woman revue Blues, Ballads and Sin-Songs (1954).

For example, friend and colleague Howard Dietz, who described her as "the swarthy, sloe-eyed houri,"[18] recalled: No one in the theatre was more discussable than Libby Holman, who came from Cincinnati and was game for anything...She did outrageous things.

For example, one Friday she said she was tired of being nice and proposed that on the weekend at the Henri Souvaines to which we were both invited we should act disagreeably instead of our usual selves.

After the show each night, the three of us would sit around till dawn drinking milk, eating coleslaw, and hating life.

"[20]Libby Holman had a variety of relationships with both men and women during her lifetime, including Jeanne Eagels, Tallulah Bankhead, Josephine Baker,[21] and, later in her life, writer Jane Bowles.

The couple's relationship lasted until Holman's death in 1971; during Libby's Broadway career in the early 1920s, they went to parties and jaunts in Harlem dressed identically in men's suits in bowler hats, joined by other lesbian and bisexual contemporaries such as Tallulah Bankhead, Beatrice Lillie, Joan Crawford, and Marilyn Miller.

[24] Although Holman's friends didn't like Reynolds, finding him moody and difficult to talk to, they tolerated his presence, as he paid for the entourage's visits to New York speakeasies and nightclubs.

[25] Reynolds threatened suicide to Holman on multiple occasions; In a letter to her, written while on an aviation journey, he once wrote: "Darling Angel.

"[26] Despite the tempestuous nature of their relationship, Holman and Reynolds married on November 29, 1931, in the parlor of the Justice of the Peace's house in Monroe, Michigan.

[citation needed] On the night of July 5, 1932, at Reynolda, Reynolds and Holman threw a 21st birthday party for Smith's childhood friend Charles Gideon Hill Jr. After the party attendees had left, with only Reynolds's best friend and secretary Albert "Ab" Bailey Walker, and Holman's friend, actress Blanche Yurka, remaining in the house, Reynolds died of a gunshot wound to the head in the morning of July 6.

Holman said she was unable to remember much of the night or the following day; the numerous testimonies given by Walker in the inquest contradicted each other.

Carpenter paid Holman's $25,000 bail at the Rockingham County Courthouse in Wentworth, North Carolina.

Holman wore a heavy veil and dark dress, and bystanders and reporters thought she was black or of mixed race—a common misconception because of her olive skin tone.

For, if Libby was the richest woman in the world (becoming richer as the men in her life died off), and also celebrated and honored with special friendships, the specter of violence tracked her from the start.

Bradshaw relates from interviews with still-living close friends that Holman called them on the telephone in a panic: "She told Louisa [Carpenter] that the Reynolds family were being horrible to her, almost as though they suspected that she had something to do with Smith's demise.

[2] In March 1939, Holman married Ralph (pronounced "Rafe") Holmes, a film and stage actor.

During World War II, she tried to organize shows for servicemen with her friend, African-American musician Josh White, but they were turned down on the grounds that "we don't book mixed company.

Libby waited till the day they were due to open, after the owners had spent a vast amount on publicity, and told them she was not going to sing in their club until they changed their racial door policy.

She had given him permission to go mountain climbing with a friend on Mount Whitney, the highest peak in California, but was unaware that the boys were ill-prepared for the adventure.

Over time, the foundation narrowed its scope to more specific causes, such as relations between Cuba and the U.S. She contributed to the defense of Benjamin Spock, the pediatrician and writer arrested for taking part in antiwar demonstrations.

She was involved in the civil rights movement and became a close friend and associate of Martin Luther King Jr.

[39] The deaths of multiple people close to her, combined with the Vietnam War and the turbulent political situation, took a toll on her mental health.

Treetops is part of the Mianus River State Park, overseen by the Connecticut Department of Environmental Protection.

In 2006, Louis Schanker's art studio on a hill overlooking the property became the home of the Treetops Chamber Music Society.