Bing Crosby (1903-1977)
Frank Sinatra (1915-1998)
Crosby's career lasted from 1926 until his death, Sinatra's from the early 1940's until shortly before his death. Both were singers and recording artists and acted in many films.
Sinatra won an Academy Award for Best Supporting Actor in "From Here to Eternity" and was nominated for best actor in "The Man with the Golden Arm." Crosby won for Best Actor in "Going My Way." In addition to "White Christmas" with Danny Kaye, Crosby appeared with Bob Hope and Dorothy Lamour in 7 "road" movies.
A crooner is a male singer of popular ballads. normally backed by a big band. Crooning had its roots in the Bel Canto of Italian opera, but with the emphasis on subtle vocal nuances and phrasing found in jazz. It was originally a negative term.