Bing Crosby

With his remarkably smooth and velvety baritone voice, Bing Crosby rose from obscurity to become the most popular singer in the world, dominating the record and singles charts for a 20-year stretch and enjoying a more than respectable popularity for the rest of his life. He also became an extremely successful actor, appearing in 70+ films, and charmed moviegoers everywhere with his relaxed performing style. Following a string of early hit singles, Crosby was recruited by Paramount Pictures and enjoyed a long-time partnership with Bob Hope on the highly popular series of "Road" movies, which served up endearing cocktails of humor and song. He was also highly impressive in many of his solo efforts, most notably "Going My Way" (1944), for which Crosby won the Best Actor Academy Award, "A Connecticut Yankee in King Arthur's Court" (1949) and "The Country Girl" (1954). Crosby's reign as one of the leading pop culture figures in America was dampened somewhat by the rise of rock-n-roll, but he maintained a huge fanbase and songs like "White Christmas," "I'll Be Seeing You" and "Swinging on a Star" were unmistakably his. Crosby's success across multiple mediums was truly remarkable and he was arguably the leading entertainment figure of the 20th century.