Billie versus Bing – A Tale of Two Singers

In his book, David Brackett (Interpreting Popular Music, 1995, Cambridge University Press) compares singers Bing Crosby with Billie Holiday. He makes the contention that although Bing was more popular at the time, it is Billie who has made the ‘lasting impression’. Let’s give a listen to the song he chooses to analyze.

It’s the song, “I’ll be seeing you”, written in 1938 by Sammy Fain and Irving Kahal. Bing Crosby’s version reached number one. Billie Holiday’s version rose as high as number four. Crosby recorded it six weeks before Billie.

Billie singing:

Bing Crosby singing:

Billie singing:

And another song I like, “Pennies from Heaven” with the lyrics of the one and only Johnny Burke:

What do you think? How important is the singer in the success of a song? Is it the style or the character you imagine? Is authenticity a criterion?

And just to set the record straight, you gotta love Crosby for songs which he ‘owned’, such as Swinging on a Star from 1944 (again Johny Burke wrote the lyrics, and Jimmy van Heusen the melody)… and of course White Christmas.