In 1934, at seventeen years of age, Forrest got her first job at WNEW, New York, singing commercials. During this time, she sang under anonymous names such as Helen, Hilee, Madlene, and Arlene. When she sang for WCBS, she became “Bonnie Blue” and “The Blue Lady of Song.” When her brother Ed, whose band was playing in Washington, D.C., called her to let her know that there was an opening for a vocalist in the Washington Madrillon Club, Forrest auditioned and soon after began singing in the popular supper club.
While performing at the Madrillon, she gained a reputation for her singing, and bandleader Artie Shaw came to see her. Shaw’s singer Billie Holiday was planning to leave the band, and in 1958 Shaw asked Forrest to go on tour. During the fifteen months she sang with Artie Shaw, his band recorded forty-one sides for RCA Victor’s Bluebird record label. In 1939, while still on the road with Artie Shaw’s band, Forrest married drummer Al Spieldock in Baltimore. Her husband remained in Baltimore, and Forrest resumed her tour. When Shaw dissolved his band, she went back to Baltimore but was soon asked to join Benny Goodman’s band. During her two-year tenure with Goodman, she recorded fifty-three sides. In 1941, she joined the Harry James band. The musical alliance of featuring Forrest’s vocals with the band as accompaniment proved very successful.
Traveling with the band, Forrest was the only woman among eighteen or more band members. She fell in love with Harry James, maintaining a sporadic love affair until James married actor Betty Grable. In 1943, a few months after James’s marriage, Forrest left the band and appeared in clubs around the country. Her husband divorced her about the same time. Forrest’s agent teamed her up with vocalist Dick Haymes, and together they appeared on their own very popular radio program, running from 1944 to 1947.
Around 1945, Forrest met Paul Hogan, an aspiring actor, at a party. The two began living together and married in 1947. They later separated and divorced in 1956. In the late 1950s, she met businessman Charlie Feinman and married him in 1959. The couple had a son, Michael, in 1960, but the marriage was dissolved in 1961. She continued to perform in major supper clubs around the country, sometimes singing for movie sound tracks as well as performing in “big band nostalgia” tours. She continued to record, achieving several hits as a soloist and several hits singing duets with Dick Haymes. Forrest recorded approximately seventy-four songs as a solo vocalist—twenty-two for Decca Records, forty for MGM, and twelve for Bell Records. In addition, she recorded for Capitol in 1955–1956, singing the hits she had sung with Harry James. From 1969 to 1974, she rerecorded some of her hits for Reader’s Digest and Time-Life as well. During various periods of “big band nostalgia,” radio broadcasts and shorts were rereleased of Helen Forrest with Artie Shaw’s band, Benny Goodman’s band, Harry James’s band, and Dick Haymes.
After Forrest's death, her only survivor was her son Michael Forrest Feinman. Feinman contacted many fans of Helen Forrest and fans of her peer Dick Haymes personally to ask them for money in exchange for momentos from Helen's private collection. Many people sent Michael money to have nothing sent back. Sadly the lack of money has resulted in no headstone for Helen Forrest. It is now over well over ten years after her death, and still nothing. I am not blaming her son, but how can an icon of the big band era not have a proper resting place is beyond me. I have tried to get in touch again with Michael Feinman, but I have had no luck.
However, Michael did address this on a another website on September 10, 2010:
I am not sure what Michael Feinman does for a living, but I know that if my mother did not have a headstone after ten years I would make sure she had something. I have talked with people in the Helen Forrest community, and they are unsure of Michael's story. I am not coming down hard on him because I have not heard his side of the story, but it is a crime and shame that a talent of the caliber of Helen Forrest is not remembered and respected more after her death. She deserves better...