During this time, Crosby became a bankable actor. He starred with Fred Astaire in the box-office hit Holiday Inn (1942), and in that musical Crosby first sang “White Christmas.” His recording of the Irving Berlin ballad became one of the most popular songs of the century, exceeded in record sales only by his “Silent Night.” Crosby then won an Academy Award for best actor for his portrayal of Father O’Malley in the film Going My Way (1944). He reprised the role in The Bells of St. Mary’s (1945), for which he received another Oscar nomination.
Crosby’s career took a turn to comedy in the series of seven “Road” films in which he appeared with Bob Hope and Dorothy Lamour, beginning with Road to Singapore (1940). Perhaps the best known in the series was Road to Morocco (1942), which was widely regarded as a classic. His other films included White Christmas and The Country Girl (both 1954); for the latter, Crosby received his third and final Academy Award nomination. He continued to act into the 1970s, many of his later appearances being on television. His last credited role was in the TV movie Dr. Cook’s Garden (1971).
Crosby ran a successful television production company in the 1960s. An astute businessman, he amassed one of the largest fortunes in Hollywood from his earnings as an entertainer and from shrewd investments. By the mid-1970s, 400 million copies of his records had been sold. He was a notable sportsman and died of a heart attack while on a golf course. His autobiography, Call Me Lucky, appeared in 1953.