Composer, arranger, trumpet player, singer and bandleader Sy Oliver was born in Battle Creek, Michigan on December 17, 1910. During his sixty-year career Oliver wrote T’aint What You Do (It’s the Way That You Do It), Yes, Indeed!, Opus One and Well, Git It! and worked with some of the most popular musical organizations of the day.

Oliver’s mother was a piano teacher and his father played several instruments including saxophone. Sy left home at the age of 17 to go on the road with Zach Whyte and his Chocolate Beau Brummels. He played trumpet and was known for his growling style and use of muted effects. He also was sometimes featured on vocal numbers. In 1933 he joined the Jimmie Lunceford band and played with them for six years. During that time he made many recordings with the band, often singing on the records. He also wrote the band’s theme song For Dancers Only.

Sy Oliver became one of the most visible Black men working with a white band when he was hired by Tommy Dorsey in 1939. Oliver was mostly responsible for writing the band’s up-tempo “hot” tunes, while fellow arranger Alex Stordahl primarily focused on the ballads. Oliver also occasionally sang with the Dorsey band, including a duet with white female vocalist Jo Stafford on 1941’s Yes, Indeed! Oliver’s arrangement of On the Sunny Side of the Street was a big hit for Tommy Dorsey.

After leaving Dorsey’s employ in 1946, Oliver worked as a freelance arranger and musical director for Decca Records. While at Decca, Oliver worked with Louis Armstrong and Peggy Lee. In 1961 he collaborated with Frank Sinatra on an album tribute to their former boss, Tommy Dorsey.

In 1974 Oliver started a ten-year nightly run at the Rainbow Room at Rockefeller Plaza in New York City which concluded when he retired in 1984. Sy Oliver passed away in May of 1988 at the age of 77.

Here is a link to the 1941 recording of Yes, Indeed! with Sy Oliver singing with Jo Stafford and the Tommy Dorsey Orchestra:

"YES, INDEED!"