Focus Features

Although Bing Crosby is rarely remembered as a Hollywood icon, he was, according to ticket sales, the third most popular actor of all time. In music, he was long considered, as AllMusic’s John Bush states, “the most popular and influential media star of the first half of the 20th century.” In 2000, when Elvis had 18 number one hits, and the Beatles 24, Crosby still ruled with 38. Born Harry Lillis Crosby, the fourth of seven children in a strict Irish-Catholic family in Tacoma, Washington, Bing seemed to approach life with unexpected ease and charm. His nicknamed Bing came from Bingo, a character from his favorite comic strip “The Bingville Bugle.”  As a kid, he did well in school, but mostly loved to play drums and sing. He ended up studying law at Gonzaga University in Spokane, but by his last year, he already knew his future lay in music. Through the ‘20s, he played with a range of successful jazz bands. But his career took a stellar leap in the ‘30s when, first, CBS started him on a series of weekly radio performances, and then he starred in the hit variety film The Big Broadcast. For the next 20 or so years, Crosby ruled radio, music and film. His series of seven Road films made in the ‘40s with Bob Hope was one for Hollywood’s most profitable franchises. Nominated for a Best Actor Oscar three times, Bing won the first time out, for Going My Way (1944). In 1948, the chummy, easy-going, pipe-chomping Crosby was polled as the most admired man in the world. On top of all that, his savvy business investments made him one of Hollywood’s richest men, leaving behind an estate estimated at about $150 million.