Streisand never officially performed at Village Vanguard, but she auditioned for Max Gordon. As Streisand told the press in 2009, her good friend Rick Edelstein asked Gordon to listen to Streisand audition. Gordon told Edelstein she was “too undisciplined” to hire.
“Miles Davis was the star of the show,” Streisand told the L.A. Times. “The opening girl singer was Joanie Sommers. My friend Rick Edelstein was the waiter and he got Miles' musicians to back me at the audition.”
“At least I did audition there, and didn't get the job," Streisand said. “Now I got the job.”
Max Gordon (who died in 1989) wrote a book about the club called Live at the Village Vanguard. Gordon related a story about Streisand and Miles Davis. Gordon asked Miles Davis to take bows and introduce the band, which Davis didn't like to do. Gordon wrote:
I knew [...] to leave Miles alone, and I did, except once when I asked him to play for a girl singer who used to hang out at the Vanguard Sunday matinees ...
“She's great,” I told him. “I heard her at a benefit.”
“I don't play behind no girl singer. Ask Herbie (Herbie Hancock, the piano player in Miles's sextet); if he wants to play for her, it's OK with me.”
When Miles heard the three numbers she did—and the applause, he said, “What's her name? Bring her in, if you want to, but hire a trio to play for her. I won't play behind no broad.”
The girl singer was Barbra Streisand. I put her into The Blue Angel later.”
Singer Carol Sloane played the Vanguard in 1961 and met young Streisand. “One of the waiters came up to me to tell me that there was a young girl in the back who looked kind or weird,” Sloane told Marc Myers. “He said she doesn't have a purse and she's wearing a T-shirt and her hair is long and stringy. The waiter asked if I wanted to see this girl or should he tell her I'm not available. I went to the back of the club and there was this ordinary looking girl. She said to me, ‘How do you do that?’ ‘Do what? You mean singing,’ I said. ‘Yeah, how do you sing like that?’ She said she was just starting out, but she may have been auditioning for the part in Wholesale.”
Sloane continued the story about meeting Streisand: “She introduced herself, and we chatted about singing for a while, and I wished her well. The next thing I knew, Columbia signed her. Many months later, I was invited to a cocktail party where Barbra was the guest of honor. She arrived and was completely made over. She really looked great. We sat down in a corner and started yapping like two old friends. She eventually waved goodbye, and I didn't see her again until years later, when I was getting my hair done at Revlon in New York [...] I sent over a note. A minute later the note came back with a note from her on the flip side asking me to come over. When I went over, Barbra was sitting in a chair with foil in her hair and both arms extended while her nails were being done and someone else was giving her a pedicure. She was absolutely charming and adorable.”
In Lorraine Gordon's book, Alive at the Village Vanguard, she wrote:
Barbra was a shy one. Nineteen years old. She wasn't a seasoned performer—she was new. Max [Gordon] took a chance on her. In fact, Max was a very generous man to Barbra early on, giving her new gigs...
Eventually he brought Barbra uptown to the Blue Angel. This would have been July 1961. That's when I got to know her. We would sit together between shows and talk. She was always alone, it seemed to me. Got up to sing in a very inconspicuous dress, kind of a muumuu, one of those long things. And I don't know why, I have this sense that she was barefoot. Maybe she was. But she had the look of a young girl. Coltish. Not dressed to kill, no sequins ... Barbra was very plain and simple.
Until she opened her mouth. Then she was transformed. Suddenly you were in the presence of this extravagantly talented woman who could give you chills just by singing. There was nothing Barbra couldn't do with her voice—she had such control, top to bottom. And she had the brains, the good sense, to pick fabulous material—each song that she sang had a different character. And she imbued them all with an emotional core of true feeling and a point of view that was altogether unique.
Barbra wasn't a jazz singer, though she could do that. She had the chops, and if it was a jazz number, yeah, she could heat it up, but she didn't particularly want to be a jazz singer. She was just a natural ...