From Benny Goodman to Woody Allen, Jews have always had a close relationship with jazz music. In this first song, jazz singer/cantor Kenny Ellis sings an awesome swingin' version of pretty much the only Hanukkah song we gentiles are aware of.
South Park has always handled Jewish issues with maturity and good taste, and the holiday season is no exception. I could have gone with "A Jew on Christmas" here, but I much prefer the Broflovski family's powerful version of The Dreidel Song (featuring Eric Cartman).
One of the few legitimate Hanukkah TV specials was 1996's "A Rugrats Chanukah". Inspired by this groundbreaking episode, here is "Rugrats Chanukah", sung by the titular babies. You can even watch the special in its entirety on the Nickelodeon site.
UPDATE: How could I forget this duet between comedy gods Stephen Colbert and Jon Stewart, from "A Colbert Christmas: The Greatest Gift of All"?
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