- Libby's decade-long obsessive, on again, off-again affair with Montgomery Clift gave her an unfortunate measure of undue influence over the sexually confused actor. It was Libby who advised Clift to turn down starring roles in both Sunset Boulevard (1950) (which had been especially written for him) and later, High Noon (1952).
- Adopted two boys, Timmy (born October 18, 1945) in 1945 while married to actor Ralph Holmes (they separated a week after) and Tony (born May 19, 1947) in 1947. They received $1 million each upon her death in 1971.
- Found slumped over in her Rolls-Royce in her garage at her 55-acre estate, Treetops, on June 18, 1971. She was 67 years old. Although she was legally drunk (.12 BAC) there were indications that she had misgivings about killing herself as the car's ignition was turned off. She had attempted several suicides previously but had been found by Schanker or the staff in time.
- Her sister, Marion Holman (nee Holzman) Tuteur was also wealthy by marriage. Like her sister she was also manic depressive and committed suicide on December 13, 1963 in San Francisco.
- Left an estate valued at $13.2 million (1971). Her beloved sprawling mansion, Treetops, was donated to Boston University. After bequests, the bulk of her estate was donated to the Christopher Reynolds Foundation.
- Established the Christopher Reynolds Foundation in 1952 in memory of her son. This foundation supported many civil rights causes of the 1950s-1960s, notably financing emerging civil rights leader Dr. Martin Luther King's 1959 trip to India to meet Prime Minister Jawaharlal Nehru. This trip was instrumental in solidifying King's conviction to non-violent protest.
- Her only child, 17-year old son, Christopher Smith "Topper" Reynolds (DOB: January 10, 1933), died in a climbing accident on California's Mt. Whitney on August 7, 1950. He had just graduated near the top of his class at Putney School in Vermont. Libby had given her son permission to go mountain climbing with a friend Stephen Wasserman, a classmate of his at the Putney School, not knowing that the boys were ill-prepared for the climb. About 10,000 feet up, they abandoned the easy trail to the top and decided to scale Whitney's 1,400-ft. east face, a cliff which had been scaled only once. Searchers later found the broken, frozen body of Stephen Wasserman. He had fallen 800 feet. Two days later, searchers found the body of Topper Reynolds jammed into a crevice high up on the cliff. Those close to Holman claim she never forgave herself. In 1952 she created the Christopher Reynolds Foundation in his memory.
- Married three times. At 27 she married 20-year-old millionaire and tobacco heir Zachary Smith Reynolds in 1931. His death received the same degree of publicity as the Charles Lindbergh baby kidnapping (or 60+ years later, the O.J. Simpson case). Although she and family friend Ab Walker were indicted for his murder in his death, the Reynolds family persuaded authorities to drop the charges. Her performing career was tarnished by the scandal. In the mid-'30s audiences would often attend her shows to hiss her or for the novelty value of seeing what all the fuss was about. This ironically also got her work, since producers felt her presence could increase the box office.
- The events surrounding her wealthy husband's death on July 4, 1932, were fictionalized by David O. Selznick in an original story, "A Woman Called Cheap", that was produced in 1935 as Reckless (1935) starring Jean Harlow. Libby took enormous satisfaction when the film flopped.
- Libby's third husband, Louis Schanker died on May 8, 1981 in Manhattan at the age of 78.
- Libby's East Hampton beach home, "The Dune House", was purchased by ABC Sports honcho Roone Arledge in the mid-'80s.
- As much as she liked Franklin D. Roosevelt, Libby hated Harry Truman. In 1948 she actively supported Henry Wallace's third-party candidacy and was one of his major financial supporters. While Truman narrowly defeated Thomas E. Dewey. Wallace garnered less than 2% of the popular vote.
- Consistently maintained she was 2 years younger than she actually was.
- Fabulously wealthy from her brief tragic marriage to tobacco heir Zachary Smith Reynolds, Libby maintained a Manhattan townhouse on 61st St. and a 16-bedroom mansion on 55 acres called "Treetops" in Stamford, CT. The estate was notable for its landscaping, which reportedly included one million daffodils, and was eventually expanded to over 100 acres.
- Libby was offered numerous opportunities to return to Broadway immediately after the Reynolds episode. The one that got away: Producer Vinton Freedley offered her the lead in what would be considered the quintessential Cole Porter 1930s Broadway musical, "Anything Goes," which she turned down. Freedley's second choice was an unknown secretary named Ethel Merman, whose performance rocketed her to fame.
- She married artist Louis Schanker in 1959. An ongoing joke between them was when Schanker would casually say to Libby, "Isn't it about time dear that you take the name Schanker." Libby, trying to keep a straight face, would always answer,"No, I think it would be a better idea if you would use the name Schanker Holman Reynolds. Actually, after their marriage, she preferred to be called Mrs. Libby Holman Reynolds Schanker which was how most newspaper articles referred to her.
- Her family was Jewish (from Germany, the Netherlands, and England).
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