Douglas was born in Chicago, Illinois, and began singing as a choirboy. By his teens he was working as a singer on a Lake Michigan dinner cruise ship. After serving briefly in the United States Navy near the end of World War II and as a "staff singer" for WMAQ-TV in Chicago, he moved to Los Angeles. There he became a vocalist in the big band of Kay Kyser, with whom he was featured on two notable hits, "Ole [or Old] Buttermilk Sky" in 1946 and "The Old Lamplighter" the following year. Kyser was responsible for giving him his show business name, and he remained part of Kyser's band until Kyser retired from show business in 1951.

In 1950, he provided the singing voice of Prince Charming in Walt Disney's Cinderella.

In the 1950s Douglas, living in Burbank, California, tried to keep his singing career going, working as house singer for a nightclub and going on the road to stay busy. He preferred not to switch to rock and roll, which limited his opportunities as big band music was declining in popularity. In the leanest years, he and his wife survived by successfully "flipping" their Los Angeles homes.

1. The Men in My Little Girl's Life 2. A House of Love 3. "A" You're Adorable (The Alphabet Song) 4. Is There a Baby in the House 5. I'd Give a Million Tomorrows (For Just One Yesterday) 6. Sunrise, Sunset 7. Let Her Be a Little Girl (A Little Longer) 8. Kids 9. The House I Live in (That's America to Me) 10. While We're Young