Dennis Day was one of the most popular American radio Irish tenors. His popularity was enhanced by his good looks and his flair for comedy. He was best known as a long-time cast member of The Jack Benny Program, the greatest and most popular broadcast program of all time, on both radio and television.
He had a clear, light Irish tenor voice, usually free of the lachrymose quality that often marred such vocalists. As a result, he was at his best in up-tempo songs, though he could sing the slower and more sentimental songs very effectively as well. He did not confine himself to Irish material, and often sang popular tunes of the day.
He has a successful recording career but was best known as a second banana with Jack Benny. Benny's program was a forerunner of all the shows in which a personality addresses the audience and serves as emcee, then falls back into being a character in a situation comedy, with breaks for musical entertainment. Unlike the program of his friend George Burns (who was always on top of things), Benny was usually increasingly frustrated by the loony characters who surrounded him, but usually as a result of his own supposed character traits, primarily stinginess and vanity.
The program began its unequalled 33-year run (counting radio and TV versions) in 1932. Dennis Day was added to the cast at the beginning of the eighth season on October 8, 1939 when a new regular singing act was needed. He was only 22 at the time. Jack's innovative format included regular interaction with his bandleader, singer, announcer, etc., who were shown as being part of his everyday life as well as his work. Dennis's light, chipper speaking voice and flair for timing -- a must in working with Benny, who was timing personified -- made him a natural as a naïve bachelor recently (and barely) our from under his mother's wing. Benny had Day build this character rapidly: The second show of the season had Dennis' mother showing up and interfering in the show as she tries to make sure her boy is being treated right.
Day constantly was portrayed as worldy-unwise, shy, bright-eyed, optimistic, and so naïve that Benny could scarcely believe it. Benny's exasperated, "Now, DENnis ... " joined his many celebrated catch-phrases. One of Day's classic bits came on a 1958 episode of the television show with a long and increasingly loopy explanation of his method for picking winning horses at the track. Another time he spoofed the popular program The Millionaire by being picked by the show's benefactor to be given the million dollars, to Jack's increasingly ill-concealed envy.
Day remained associated with the show through the last airing of the TV show on April 16, 1965. Along the way, he was also the star of his own popular radio program, a spin-off from the Benny program that aired on NBC with 212 episodes from October 3, 1946 through June 30, 1951. The premise of the show was that as stingy Jack Benny's tenor Dennis was, of course, under-paid, so he had to get a succession of odd jobs while carrying on the life of a bachelor in Hollywood. At times he dreamed himself into Walter Mitty-like situations.
He also had parts in movies, including the second male lead in a musical called Never, Never with Dale Robertson and Mitzi Gaynor.