Early Life
Gilbert was born in Newport News, Virginia, and began his career as a choir boy in the Lutheran Church in that city. Although his parents had never worked in the theatrical profession themselves, his grandmother had been a church singer. While he was still in high school, Gilbert decided to take up a professional singing career and learned from an opera teacher. Although he never sang any opera independently, he was the regular vocalist with Shelly Harmon and His Orchestra, a group which toured the Virginia area.
A few years after graduating from high school, Gilbert heard about an audition as regular vocalist for the Dean Hudson Orchestra which was being conducted in Jacksonville, Florida. Unfortunately, Gilbert was confused about the dates and upon his arrival, he learned that the position had already been filled. However, a local agent in Jacksonville needed a master of ceremonies for the Sky Way club there. Gilbert was asked if he was an emcee, but was unaware of what an emcee was, as in Virginia there were no clubs at the time, and he had never lived outside that state. While he was trying to figure everything out, the agent told him that he had received his job as emcee. Gilbert resided in Florida for three months, during which time he received on-the-job training, and learned to walk on stage, speak in front of a public crowd, and tell jokes and stories.
The famous "Dead End Kids," a group which comprised such young actors as Leo Gorcey, Huntz Hall, and Gabriel Dell, were organizing a revue. Gilbert joined that group and played throughout the southwestern portion of the United States for sixteen weeks. When they played in Norfolk, Gilbert himself even got special billing.
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