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Initially a piano prodigy, her interest in music developed from exposure to her mother's professional chorus singing work. At age 16 or 17, working as secretary at Twentieth Century Fox, Olay undertook singing lessons with vocal coach Florence Russell (Dorothy Dandridge). While at work, she met one of Duke Ellington's vocalists, Ivie Anderson. Together they attended the venue where Ellington was playing and Olay was persuaded to sing. In 1942, at her mother's re-marriage party she sang and impressed a guest, the wife of songwriter Irving Gordon (Throw Mama From the Train, Unforgettable). Gordon in turn introduced Olay to jazz musician Benny Carter who became her musical mentor.

She performed under the moniker Rachel Davis and, due to her dark complexion, passing as a black woman, with Carter in San Diego, and later with Jerry Fielding in Los Angeles and Beverly Hills clubs, all the while holding down a secretarial day job at Twentieth Century Limited, including work for celebrated screenwriter Preston Sturges. At the Cabaret Concert Theatre where she both waitressed and sang, she came to the attention of Bill Hitchcock of Zephyr Records. Olay's first LP on Zephyr in 1956 was promoted as coming from "the blues shouting tradition", "pop style" and "swinging interpretation".

While gigging at the Little Club, Olay was approached by Bill Burton, who managed, among others, Jimmy Dorsey and Dick Haymes, and soon got her big break when Burton booked her an emergency gig at the Avant Garde Club in replacement of Billie Holiday, who had fallen ill. This developed into a headline run, along with Shelley Berman, Matt Dennis Trio and Lenny Bruce. A regular at the club was arranger Peter Ruggolo, who A&R'ed for Mercury Records.

Her first LP on Mercury OLAY! in 1958 was followed by a guest vocalist spot on Jack Paar's Tonight Show. She became the "Singing Sensation of the Jack Paar Show" during Paar's stint, and also appeared later on Johnny Carson's watch, the latter time backed by Duke Ellington. Subsequent appearances included Jerry Fielding's TV show, and with Merv Griffin, Jackie Gleason and Steve Allen. In 1961, Olay found time to play the role of Julie in Lewis & Youngs' production of Showboat.

For the second LP Easy Living on Mercury in 1959, Olay was set up with Jerry Fielding whose credits included arranging with big bands such as those of Kay Kyser, Claude Thornhill, Jimmie Lunceford, Tommy Dorsey, Charlie Barnet, and Les Brown. LP's followed on diverse labels after Olay's departure from Mercury and she continued nightclub appearances and TV shows well into the 1960s (e.g.: Sue Rainey on KTLA June 11, 1965). After spending some time performing in Europe where the popularity of American jazz persisted Olay returned to the USA and gradually phased into retirement and withdrew from singing altogether.

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