After finishing high school in 1920, Crosby attended Gonzaga University for several years, but in 1923 dropped out to pursue a vaudeville career with his friend Al Rinker. The duo performed as “Two Boys and a Piano,” singing songs and telling jokes, which led to collaboration with various jazz ensembles and eventually landed Crosby a regular radio gig with CBS, where he hosted a show that would run under various titles for a solid three decades (via Biography).

An innovator in radio, Crosby was the first to pre-record his programs onto magnetic tape, which was at first controversial with the networks, who preferred live broadcasts, but eventually became widespread throughout the industry. Crosby took the practice with him when he went on to television, going so far as to invest in the companies who produced the tape and recording equipment.

During World War II, Crosby performed for the troops and was voting the “most positive influence” on troop morale, beating out everyone from President Franklin Roosevelt to Bob Hope. As a singer, Crosby was mainly noted for the introduction of a “crooning” singing style to the American pop landscape. Previously, most pop singers had focused on “belting” — singing loudly from the chest — to reach the back seats in the theater. Crosby, however, being ever the lover of technology, employed a smoother, quieter singing style made possible by the use of what were then cutting-edge microphones and amplification.