About Chester Gaylord
Lived 1899 – 1984 (aged 85). Chester Gaylord was an American singer.
Chester Gaylord (February 24, 1899 – July 1, 1984) was a vocalist and among the most active of recording artists in the United States during the late 1920s through the early 1930s. He was known as The Whispering Serenader on radio and on his phonograph records.
He began his career as a singer and announcer for radio station WTAG in Worcester, Massachusetts in the early 1920s. Chester Gaylord's first recordings (in 1920) were saxophone solos for Thomas Edison, whom he had met. In 1923, he signed with Columbia records and made a number of vocal records for them. His popularity spread rapidly leading Brunswick Records (the second largest record company in the United States in the 1920s) to offer him an exclusive contract. He became one of the labels most prolific vocalists during the late 1920s. After the Warner Brothers bought out the Brunswick Record company in April 1930 a reorganization occurred and Chester Gaylord's contact was one of numerous artists whose contract was not renewed. Chester Gaylord continued to be popular on radio throughout the early 1930s until the introduction of swing music, in 1935, a type of music that was unsuitable to his style of singing. From 1929 to 1931, he was a featured vocalist on NBC radio on the Top Notchers Coca-Cola Radio Program with Leonard Joy and his All String Orchestra.
Gaylord moved to WBZ in Boston in the late 40s, and completed his broadcasting career there. He retired sometime in the mid-1960s. During his retirement years he lived in Sterling, Massachusetts. He regularly played 1920s and 1930s songs on piano at The Old Timer, an Irish Pub in neighboring Clinton, Massachusetts. According to Gaylord's obituary, he was still performing right up until a few weeks before his death.
Works
Pianist
Thinking of Me Thinking of You (1928) My Window of Dreams (1928) Here's the Party Now in Person (1928) You're in Love and I'm in Love (1928) My Inspiration is You (1928) Me and the Man in the Moon (1928) Glad Rag Roll (1929) Honey (1929)
Vocalist
My Troubles are Over (1929) Mean to Me (1929)
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Important facts
People in Chester Gaylord's life
Named in this biography and alive at the same time
Contemporaries
People whose lives overlapped Chester Gaylord's
Frequently asked questions
Who was Chester Gaylord?
American singer (1899-1984)
When was Chester Gaylord born?
Chester Gaylord was born on 24 February 1899.
When did Chester Gaylord die?
Chester Gaylord died on 1 July 1984.
What was Chester Gaylord's occupation?
Chester Gaylord was a singer.
What nationality was Chester Gaylord?
Chester Gaylord was American.
Sources & further reading
Cite this page
APA: Biography.guide. (2026). Chester Gaylord. https://biography.guide/chester-gaylord/
MLA: "Chester Gaylord." Biography.guide, https://biography.guide/chester-gaylord/.
Chicago: "Chester Gaylord." Biography.guide. https://biography.guide/chester-gaylord/.
Data last updated: 2026-09-20 · Spot an error? Report a correction.
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