Tuesday, April 14, 2015

Worcester’s Whispering Serenader

By Chet Williamson

He was among America’s first generation of popular singers known as crooners. Along with such American vocal giants as Bing Crosby, Rudy Vallee, and Gene Austin, Worcester-born vocalist Chester Gaylord sang in this style with a soft fluttering approach that earned him the moniker of the "Whispering Serenader."

Unlike Crosby, Vallee and Austin, history has not accorded Gaylord his due as a legendary singer. However, the fact remains, he was among the most active and recorded artists of the 1920s and ‘30s.

Gaylord was born in Worcester on February 24, 1899. He was a graduate of Worcester Academy, where it was said that he "ached to get into the music business." He studied with with J. Edward Bouvier, director of the Holy Cross College Band.

He entered the military in 1917 just as America entered World War I and played saxophone in the Navy band at Newport. After the war, Gaylord moved to New York City and worked with, among others, Tommy and Jimmy Dorsey, Burt Lowe, Red Nichols, and Paul Whiteman.  

According to his obituary, Gaylord returned to Worcester in 1924 "after being chosen from 500 applicants as chief announcer for WTAG." He was the station's first employee. "I put together the station's programs, did the announcing, played for singers and, and whenever there was an open spot, I played the piano and sang," he once told a Worcester Telegram reporter.

In the August 16, 1998 edition of the Worcester Telegram & Gazette, under the headline of “WTAG was City's Chief Broadcast Resource,” local historian Albert B. Southwick wrote: “As the premier radio station of Worcester County, WTAG played a key role in Worcester's life and progress for more than 50 years. The strength of WTAG came from its solid roots in the community. Dol Brissette, one of the chief programmers, began his career as a band leader playing for dances at the Hotel Bancroft's Starlight Roof, and his orchestra was featured on WTAG. One of the early regulars was Chester Gaylord at the piano. He was a longtime favorite, almost the signature hallmark of WTAG."

Gaylord was first committed to wax as a saxophonist and not a vocalist. The early sides were recorded in 1921 by Thomas Edison on cylinders known as “diamond discs.” The tunes documented are “Love’s Old Sweet Song” and “Sweet and Low.” He also recorded for Columbia, Brunswick, Okeh, and Melotone records.

In 1923, playing saxophone, Gaylord recorded the single, “Baby Blue Eyes,” for Okeh with pianist Justin Ring. That same year, Gaylord signed with Columbia and made a raft of vocal records with the company under his own name. They are “Montmartre Rose,” “On My Ukulele,” “Who Takes Care of the Caretaker’s Daughter,” and “There’s One Born Every Minute,”  “Insufficient Sweetie,” “My Sugar,” and “Her Have Gone.”

Other Columbia sessions feature Gaylord singing in a vocal ensemble with Paul Whiteman and His Orchestra. He was paired with other popular vocalists of the day, including Bing Crosby, Al Rinker, Austin Young, Jack Fulton, and Harry Barris. Those sides are “Let’s Do It, Let’s Fall in Love,” “Evening Star,” “Last Night I Dreamed You Kissed Me,” “Get Out and Under the Moon,” “No More Worryin’,” “I’m in Love Again,” “Fallen Leaf,” “My Blue Heaven,” “The Calinda,” “Shanghai Dream Man,” “Ooh, Maybe It’s You,” “Why Do You Roll Those Eyes at Me,” “It Was the Dawn of Love.” 

According to Wikipedia, Gaylord’s “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 label's most prolific vocalists during the late 1920s.”

Between 1927 and 1931, Gaylord recorded more than 50 sides in New York City. Some of the studio musicians on the dates included many of the top players on the scene, including jazz stalwarts Tommy and Jimmy Dorsey, trumpeter Manny Klein, and guitarist Dick McDonough. Topping the list of tunes Gaylord recorded for the label are such classics as “My Baby Just Cares for Me” (Gus Kahn and Walter Donaldson), “Blues in the Night” (Johnny Mercer), and “Just You, Just Me” (Jesse Greer and Raymond Klages).

In addition to accompanying himself on the piano on many of the sides, Gaylord is also supported by a collection of bands. He sang with the Joe Rines Band, Jack Denny’s Orchestra, Jacques Renard and His Orchestra, Castlewood Marimba Band, and Red Nichols and His “Strike Up The Band” Orchestra. The Nichols recordings featured among others, the Dorseys, Charlie Teagarden, Glenn Miller, and Gene Krupa. "As a Brunswick recording 'houseman,' he also played saxophone with Dr. Frank Black and Gus Haenschen orchestras, and was once described as a 'saxophone virtuoso," the Telegram noted.

In 1930, Warner Brothers bought out the Brunswick Record company. Wiki notes that a reorganization occurred and Chester Gaylord's contact was one of numerous artists whose deal 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.”
The history of the program is documented on the website known as Digital Deli (edited by Steve Ditlea).  On a show that was aired at 10:30 p.m. on November 26, 1930, Gaylord appeared with the playwright Ring Lardner and sang a collection of standards such as “Something to Remember You By,” “Three Little Words,” and “I’m Confessin’ That I Love You.”

The site states that “Coca-Cola made their first entry into Radio network programming in 1930, with 'Coca-Cola Top Notchers,’ a weekly, live (then later for syndication), 30-minute Sports/Variety show, which aired on Wednesday nights over the NBC 'Red' Network from 10:30 to 11:00 pm. Popular New York Herald Tribune sportswriter and commentator Grantland Rice presided over the show for its run.”

Bandleader Leonard Joy was also an arranger for RCA records. He was involved in two of the more historic moments in the annals of jazz. He was an assistant director with Paul Whiteman, who was involved in the 1928 recording of “San” by Bix Beiderbecke. And, on October 11, 1939, Joy was the studio producer for Coleman Hawkins landmark take on “Body and Soul, a recording that the Library of Congress has placed into the National Recording Registry.

Gaylord also appeared on radio with bands led by Ted Fio Rito, Ben Pollack, and Ben Selvin. According to Wiki, Gaylord moved to WBZ in Boston in the late 1940s, and “completed his broadcasting career there. He retired sometime in the mid-1960s.” In a feature article on the history of WBZ Radio, Donna Halper wrote: “November 26, 1946: WBZ’s 25th anniversary celebration features performers from the early days along with current stars. Had you listened back then, you would have heard such popular entertainers as country singer Georgia Mae and her Buckaroos, vocalists like Ray Dorey and Chester Gaylord, and courageous Dotty Myles, who despite having been severely burned in 1942’s Cocoanut Grove fire, was making a musical comeback.”

Harper later added on a WBZ bulletin board the comment: “In the course of my research, I have found all sorts of interesting stuff about Chester Gaylord, the former chief announcer of WTAG in Worcester (their first announcer in fact, way back in 1924 when the station went on the air as WCTS), who was also a prolific recording artist during the golden age of radio and beyond. He made a number of hit records during the 78 rpm era, and sang on NBC as well as on the Yankee Network. 

“According to his obituary (he died in 1984, at the age of 85, and was still performing right up until a few weeks before his death!), he moved to WBZ in the late ‘40s, and finished his  broadcasting career there -- but I do not recall him at WBZ, although I have seen his name in printed materials from the station.”

The Old Timer, Clinton
Though retired from radio, Gaylord remained an entertainer. "One of his favorite playing spots was The Old Timer Restaurant in Clinton," reports the Telegram.
Chester W. Gaylor, the Whispering Serenader, died on July 1, 1984.

Note: This is a work in progress. Send all comments, corrections, and suggestions to: walnutharmonicas@gmail.com Thanks for taking the time. I appreciate it. Also see: www.worcestersongs.blogspot.com.




  1. Wow, great information. I have a lot of Bing's work and the Big Bands but I had never heard of this individual. I will need to check him out. Thanks,

  2. Interesting topic for a blog. I have been searching the Internet for fun and came upon your website. Fabulous post. Thanks a ton for sharing your knowledge! It is great to see that some people still put in an effort into managing their websites. I'll be sure to check back again real soon.
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  3. Dear Mr. Williamson,

    First of all, I would like to congratulate you on your very nice article about Chester Gaylord, who has always been one of my favorite among the forgotten crooners of the 1920s and '30s. I publish a blog about classic jazz, big bands, and the music of the crooners called The Vintage Bandstand. You may read it here:


    Recently I've been doing some research for a piece on Chester Gaylord, and that is how I found your website and your article on Gaylord, which I really enjoyed reading. As you know, not much has been written about Gaylord, so I was pleasantly surprised to find an article that was so informative. As you also probably know, no CDs featuring Chester's recordings are currently available, though fortunately the Internet Archive offers quite a few of his recordings and radio cuts for free download, and with fairly good sound.

    Besides congratulating you on your piece on Chester Gaylord, I wanted to offer a little correction. I have found no evidence that Chester ever recorded with Paul Whiteman. The Whiteman orchestra had a Charles Gaylord within its ranks, a violinist who also sang as part of the sweet trio, often backing Bing Crosby. But Charles and Chester Gaylord are two different people. Though Chester sang, he could not play the violin, and even though he did record in New York City, he was never a featured singer with the Whiteman band. I am absolutely certain that Charles and Chester Gaylord are not the same person, moreover, because I have a picture of Charles Gaylord (on page 45 of Leo Walker's book The Wonderful World of the Great Dance Bands) and he looks nothing like the pictures I know of Chester Gaylord.

    I simply wanted to let you know in case you would like to modify the content of your piece on Chester, on which I congratulate you again.



    P.S.: My article on Chester Gaylord, very much indebted to yours, is now available here:


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