Bing Crosby was already a beloved musician when Frank Sinatra was growing up. As a kid, Sinatra aspired to follow in Crosby's footsteps, but as he emerged from his shadow, Crosby's career begins to wane. Both developed their own signature styles, but fought to keep their careers alive. Over the years, the two beloved crooners would both battle and collaborate as they vied for fame in the ever-fickle world of music, film, and television.