Bing Crosby started out within a jazzy vaudeville act and band singer, alongside his friend, Al Rinker, in the mid-1920s. He made his film début in The King of Jazz, in 1930 before beginning his popular radio program, in 1931- a success that lasted 30 years. Alongside various musical comedies during the 1930s that helped American audiences forget the dark days of the Depression, he began the adventure of the popular Road to films in which he co-starred alongside Bob Hope – the two becoming faithful friends on and off screen. He specialized in sentimental productions such as Holiday Inn, opposite Fred Astaire and in which he sang one of his greatest hits, White Christmas, he also starred in Going My Way, in 1944 and High Society, in 1956, alongside Grace Kelly. Although he had always preferred playing reassuring roles, he accepted dramatic parts during the 1950s in such films as The Country Girl, in 1954. From the 1960s, he focused on television where he hosted numerous programs including Christmas specials during the 1970s, on which he performed a memorable duet with pop rock icon, David Bowie – or how to make Christmas classics become ultimately cool. The charming and easy-going crooner definitely changed the sound of popular music: combining crowd-pleasing and artistry.