Aged 16 and then living on her own, Streisand's youth and ambition worked in her favor, but she lacked a mature woman's physical features which were needed for serious female roles. She therefore took various menial jobs to have some income. At one period, she lacked a permanent address, and found herself sleeping at the home of friends or anywhere else she could set up the army cot she carried around to save on rent expense. When desperate, she would return to her mother's flat in Brooklyn for a home-cooked meal. However, her mother would be horrified by her daughter's "gypsy-like lifestyle," wrote biographer Karen Swenson, and again begged her to give up trying to get into show business;:6 but Streisand took her mother's pleadings as even more reason to keep trying: "My desires were strengthened by wanting to prove to my mother that I could be a star.":6

She took a job as an usher at the Lunt-Fontanne Theater for The Sound of Music, early in 1960. During the run of the play, she heard that the casting director was auditioning for more singers, and it marked the first time she sang in pursuit of a job.:6 Although the director felt she was not right for the part, he encouraged her to begin including her talent as a singer on her résumé when looking for other work.:6

That suggestion prodded Streisand to think seriously about a singing career, in addition to acting. She asked her boyfriend, Barry Dennen, to tape her singing, copies of which she could then give out to possible employers. Dennen had acted with her briefly in an off-Broadway play but had no reason to think she had any talent as a singer, and she never mentioned it. Nevertheless, he agreed and found a guitarist to accompany her:

We spent the afternoon taping, and the moment I heard the first playback I went insane ... This nutty little kook had one of the most breathtaking voices I'd ever heard ... when she was finished and I turned off the machine, I needed a long moment before I dared look up at her.:6

Dennen grew enthusiastic and he convinced her to enter a talent contest at the Lion, a gay nightclub in Manhattan's Greenwich Village. She performed two songs, after which there was a "stunned silence" from the audience, followed by "thunderous applause" when she was pronounced the winner.:7 She was invited back and sang at the club for several weeks. It was during this time that she dropped the second "a" from her first name, switching from "Barbara" to "Barbra", due to her dislike of her original name.

Nightclub shows and Broadway stage

Streisand was next asked to audition at the Bon Soir nightclub, after which she was signed up at $125 a week. It became her first professional engagement, in September 1960, where she was the opening act for comedian Phyllis Diller. She recalls it was the first time she had been in that kind of upscale environment: "I'd never been in a nightclub until I sang in one.":7

Dennen now wanted to expose Streisand to his vast record collection of female singers, including Billie Holiday, Mabel Mercer, Ethel Waters, and Édith Piaf. His effort made a difference in her developing style as she gained a new respect for the art of popular singing. She also realized she could still become an actress by first gaining recognition as a singer.:7 According to biographer Christopher Nickens, hearing other great female singers benefited her style, as she began creating different emotional characters when performing, which gave her singing a greater range.

Feeling more self-confident, she improved her stage presence when speaking to the audience between songs. She discovered that her Brooklyn-bred style of humor was received quite favorably.[25]:8 During the next six months appearing at the club, some began comparing her singing voice to famous names such as Judy Garland, Lena Horne and Fanny Brice. Her conversational ability to charm an audience with spontaneous humor during performances became more sophisticated and professional.:8 Theater critic Leonard Harris, in one of his reviews, could already envision her future success: "She's twenty; by the time she's thirty she will have rewritten the record books."

Nightclub shows and Broadway stage

Eleanora Fagan, better known as Billie Holiday, was an African American jazz singer with a career spanning nearly thirty years. Nicknamed "Lady Day" by her friend and music partner Lester Young, Holiday had a seminal influence on jazz music and pop singing. Her vocal style, strongly inspired by jazz instrumentalists, pioneered a new way of manipulating phrasing and tempo. She was known for her vocal delivery and improvisational skills.

Streisand was next asked to audition at the Bon Soir nightclub, after which she was signed up at $125 a week. It became her first professional engagement, in September 1960, where she was the opening act for comedian Phyllis Diller. She recalls it was the first time she had been in that kind of upscale environment: "I'd never been in a nightclub until I sang in one.":7

Dennen now wanted to expose Streisand to his vast record collection of female singers, including Billie Holiday, Mabel Mercer, Ethel Waters, and Édith Piaf. His effort made a difference in her developing style as she gained new respect for the art of popular singing. She also realized she could still become an actress by first gaining recognition as a singer.

Mabel Mercer was an English-born cabaret singer who performed in the United States, Britain, and Europe with the greats in jazz and cabaret. She was a featured performer at Chez Bricktop in Paris, owned by the hostess Bricktop, and performed in such clubs as Le Ruban Bleu, Tony's, the RSVP, the Carlyle, the St. Regis Hotel, and eventually her own room, the Byline Club. Among those who frequently attended Mercer's shows was Frank Sinatra, who made no secret of his emulating her phrasing and story-telling techniques.

Ethel Waters was an American singer and actress. Waters frequently performed jazz, swing, and pop music on the Broadway stage and in concerts, but she began her career in the 1920s singing blues. Waters notable recordings include "Dinah", "Stormy Weather", "Taking a Chance on Love", "Heat Wave", "Supper Time", "Am I Blue?", "Cabin in the Sky", "I'm Coming Virginia", and her version of "His Eye Is on the Sparrow". Waters was the second African American to be nominated for an Academy Award. She was the first African-American to star on her own television show and the first African-American woman to be nominated for a Primetime Emmy Award.

Judy Garland was an American actress, singer, dancer, and vaudevillian. During a career that spanned 45 years, she attained international stardom as an actress in both musical and dramatic roles, as a recording artist, and on the concert stage. Respected for her versatility, she received a Juvenile Academy Award, a Golden Globe Award, and a Special Tony Award. Garland was the first woman to win the Grammy Award for Album of the Year for her live recording Judy at Carnegie Hall (1961).

Lena Mary Calhoun Horne was an American singer, dancer, actress, and civil rights, activist. Horne's career spanned over 70 years appearing in film, television, and theater. Horne joined the chorus of the Cotton Club at the age of 16 and became a nightclub performer before moving to Hollywood.

Fania Borach, known professionally as Fanny Brice or Fannie Brice, was an American illustrated song model, comedienne, singer, theater, and film actress who made many, stage, radio, and film appearances. She is known as the creator and star of the top-rated radio comedy series The Baby Snooks Show. Thirteen years after her death, Brice was portrayed on the Broadway stage by Barbra Streisand in the 1964 musical Funny Girl; Streisand also starred in its 1968 film adaptation, for which she won an Oscar.