Dick Whitman first formed an orchestra in the Omaha, Nebraska, area in 1941 but disbanded it when he was drafted the following year. In the late 1940s he put together a new outfit which became a popular attraction in the upper Great Plains and Midwest. Wickman toured primarily in his native Nebraska, Iowa, and the Dakotas. His music, a mixture of dance band rhythms and polkas, reflected regional tastes. The group made several recordings on Wickman's on Wick label.
From 1965 to 1968 Wickman's orchestra was featured in its own half-hour program on local radio in Lincoln, Nebraska, and also performed on a weekly television program. Wickman's broadcasts attracted national attention and earned him his own radio program on the CBS network from 1969 to 1970, remote from the Roseland Ballroom in New York City. In the early 1970s he sidelined the orchestra to focus on other business ventures but came back to the music business in the late 1970s as leader of the retired Jan Garber's orchestra, a post he maintain through the mid-1980s.