The news went around the world. MADONNA SANG 2 YIDDISH SONGS for her kabbalah professor Phillip Berg. Yet, In all the articles I read on the Internet, and there are many, no one was able to indicate the titles of the songs she sang. If someone knows, please let us know.
You don't have to be Jewish to sing Yiddish songs. In the 1960's and in one of her first albums Joan Baez sings a beautiful English version of Dona, Dona. The Andrews sisters became an international sensation when they sang BEI MIR BISTU SCHOEN in the 1940's. This music was later classified as YIDDISH SWING. And included songs by Benny Goodman. Dinah Shore (yes, she's Jewish) had a hit with an English version of YES, MY DARLING DAUGHTER in the 1940's.
Celia Cruz (the Latin salsa queen) recorded a salsa version of Hava Nagillah, and there are rumors that she recorded a version of My Yiddishe Mame in Havana, Cuba in the 1940's-1950's, but I can not confirm it.
And all the male vocalists of the 1960's recorded selections from FIDDLER ON THE ROOF: for example, Robert Goulet, John Gary, Jerry Vale, Tony Bennett...etc. Sinatra? I don't recall any Jewish song recorded by him, although he had many Jewish friends.