Born in Worcester, MA, in 1899, Gaylord showed an early interest in music, and during the First World War he joined the US Navy and put his saxophone-playing skills to work. Upon his return to civilian life, Gaylord briefly moved to New York, but the opportunity to work as an announcer on local radio prompted him to return to his hometown. It was then that he began his broadcasting career, jumping at any chance he had to play piano and sing over the airwaves. His frequent appearances were consistently well received by the radio audience, which must have played some part in his signing a recording contract with Columbia as a vocalist in 1923. After this stint on Columbia, Gaylord signed with Brunswick, another one of the major labels at the time, and subsequently made some of the best records of his career, accompanied by some of the jazz greats that we have already mentioned. Many of the tunes Gaylord recorded in these jazzy settings at these New York sessions, like "Mean to Me," "Memories of You," or "Glad Rag Doll" would in time become standards, and it is interesting to note that he would often sing the verses, some of which are now rarely heard.
During these busy years, Gaylord also found time to provide vocal refrains on dance band records by the likes of Jacques Renard, Jack Denny, and Red Nichols, while he also maintained a hectic scheduled on the radio, appearing on popular shows such as the Top Notchers Cola Cola Program. As a matter of fact, when Brunswick decided not to renew his recording contract sometime in 1930-31, the future of Gaylord's career lay on the airwaves, singing with excellent bands like those led by Ben Selvin, Ted Fio Rito, and Ben Pollack and eventually accepting a job on Boston's WBZ in the late 1940s. By the mid-'60s, Gaylord had quit doing radio work, though he kept performing occasionally as a singing pianist until his passing in 1984. To the best of my knowledge, no CD is available documenting Gaylord's career at the time of this writing, but fortunately, an extensive collection of his recordings and even some radio cuts can be found on the Internet Archive here, with fairly good sound. Hopefully one day a reissue label will decide to bring Gaylord out of obscurity, something that his outstanding recordings definitely deserve.
Very little has been written about Chester Gaylord, so I am indebted to a very interesting article that Mr. Chet Williamson published in 2015 in his blog, Jazz Riffing on a Lost Worcester, and that you may access here.