I opted not to write a whole post on this topic. I wanted to. I thought that I might but I am lacking the passion. So instead you can go to Treppenwitz and see what prompted my thought.
One more comment about this. In my experience Havdalah and Adon Olam were the most frequent targets of being sung to an alternative tune, such as the theme to Cheers, Oklahoma or Back In The Saddle Again.
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Annie,
It all depends on who is doing it. Some voices are just awkward.
Trep,
Agreed.
I think Kedusha of Musaf is by far the most fertile ground for lapses in judgement by the person leading the service.
The only piece of liturgy that I enjoy when sung to an alternative tune is the blessing for Rosh Chodesh done the week before in shul. I think that it is cute when the baal tefila sings it to the tune of a holiday song for the upcoming month.
There is one month without a single holiday and my old Jewish Studies teacher would sing the blessing to the tune of “Happy Birthday” b/c it was his birthday month. Otherwise, I have ZERO interest in showtunes during davening.