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The Straw Hat Revue opened on September 29, 1939, and closed after 10 weeks, but critics took notice of Kaye's work. His next venture was a short-lived Broadway show with Sylvia Fine as the pianist, lyricist, and composer. He was working in the Catskills in 1937 under the name Danny Kolbin.

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The Kaye series ended abruptly when the studio shut down in 1938. He usually played a manic, dark-haired, fast-talking Russian in these low-budget shorts, opposite young hopefuls June Allyson and Imogene Coca. In 1937, Kaye's film debut came from a contract with New York–based Educational Pictures for a series of two-reel comedies. After the dancer dropped a fan while trying to chase away a fly, Kaye was hired to watch the fans so they were always held in front of her. One job was working in a burlesque revue with fan dancer Sally Rand. Jobs were in short supply when Kaye returned to the United States, and he struggled for bookings. His interest in cooking began on the tour. The waiter nodded in understanding, bringing Kaye two eggs.

Kaye flapped his arms and clucked, giving the waiter an imitation of a chicken. Kaye's daughter Dena relates a story her father told about being in a restaurant in China and trying to order chicken. Sometimes, he found them necessary when ordering a meal. The experience of trying to entertain audiences who did not speak English inspired him to do the pantomime gestures, songs, and facial expressions that eventually made his reputation. To calm them, Kaye went on stage holding a flashlight to illuminate his face and sang every song he could recall as loudly as he was able. With no power, the audience became restless and nervous. By evening's performance time, the city was in the grip of the storm. The strong wind hurled a piece of the hotel's cornice into Kaye's room. The troupe's hotel suffered heavy damage. During its stay in Osaka, Japan, a typhoon hit the city. The troupe left for a six-month tour of Asia on February 8, 1934. The act toured the United States and in Asia with the show La Vie Paree. They opened in Utica, New York, where he used the stage name Danny Kaye for the first time.

Kaye's first break came in 1933 when he joined the Three Terpsichoreans, a vaudeville dance act. He learned his trade in his teenage years in the Catskills as a tummler in the Borscht Belt. In 1939, Kaye met the same dentist's daughter, Sylvia Fine, at an audition, and in 1940 they eloped. A dentist who hired him to look after his office over lunch and run errands fired him when he found Kaye using his dental drill on the office woodwork. He lost the insurance job when he made an error that cost the insurance company $40,000 ($600,000 in 2019 adjusted for inflation). He held a succession of jobs after leaving school, as a soda jerk, auto insurance investigator, and office clerk. Kaye said that as a young boy, he had wanted to be a surgeon, but the family could not afford a medical education. When Kaye returned to New York, his father did not pressure him to return to school or work, giving his son the chance to mature and discover his own abilities. Kaye sang while Louis played the guitar and the pair eked out a living for a while. Not long after, Kaye and his friend Louis ran away to Florida.

His mother died when he was in his early teens. He attended Thomas Jefferson High School in Brooklyn, but he did not graduate. He attended Public School 149 in East New York, Brooklyn (eventually renamed to honor him) -where he began entertaining his classmates with songs and jokes.

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His parents and older brothers Larry and Mac left Dnipropetrovsk (then part of Novorossia, Russian empire) two years before Danny's birth he was their only son born in the United States. David Daniel Kaminsky was born in Brooklyn, New York, on Janu(though he would later say 1913), to Ukrainian–Jewish immigrants Jacob and Clara ( née Nemerovsky) Kaminsky.