So here we go...
The absolute winner would have to be:
#8 'Minnie the Moocher' by Cab Calloway & His Orchestra (1931)
Highlights:
(There are some good songs that I've left out but my original list was 20 songs long)
#1 'O Sole Mio' by Enrico Caruso (1916)
#3 'Allons à Lafayette' by Joe and Cléoma Falcon (1928)
#6 'St. James Infirmary Blues' by Louis Armstrong & His Hot Five (1929)
#9 'Need a Little Sugar in My Bowl' by Bessie Smith (1931)
#16 'Strange Fruit' by Billie Holiday (1939)
#17 'Over the Rainbow' by Judy Garland (1939)
#19 'Mbube' by Solomon Linda & the Evening Birds (1939)
#20 'The Java Jive' by The Ink Spots (1940)
#21 'Gloomy Sunday' by Billie Holiday (1941)
#23 'God Bless the Child' by Billie Holiday (1941)
#25 'Rum and Coca-Cola' by Lord Invader (1943)
#27 'Lili Marleen' by Marlene Dietrich (1945)
#31 'La Mer' by Charles Trenet (1946)
#32 'White Christmas' by Bing Crosby (1947)
#34 'Nature Boy' by The Nat King Cole Trio (1948)
Songs that I found particularly tedious:
#5 'Pokarekare' by Ana Hato (1929)
#14 'Cross Road Blues' by Robert Johnson (1936)
#29 'Al Gurugu' by La Nina de los Peines (1946)
Suggest you try this version of Pokarekareana (sung by Hayley Westenra) http://www.youtube.com/watch?v=pj2e6fVn1Lw
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