Harry Lillis "Bing" Crosby Jr. was an American singer, actor, television producer, television and radio personality, and businessman. The first multimedia star, he was one of the most popular and influential musical artists of the 20th century worldwide. Crosby was a leader in record sales, network radio ratings, and motion picture grosses from 1926 to 1977. He was one of the first global cultural icons. Crosby made over 70 feature films and recorded more than 1,600 songs.

Francis Albert Sinatra was an American singer and actor. Nicknamed the "Chairman of the Board" and later called "Ol' Blue Eyes", he is regarded as one of the most popular entertainers of the mid-20th century. Sinatra is among the world's best-selling music artists, with an estimated 150 million record sales globally.