Florian Boesch is a fine baritone, known equally for his opera and lieder performances. He has worked with many of the outstanding conductors and ensembles. Here he is performing the Tom Waits song:
To be fair, let's hear Florian Boesch doing some of his usual repertoire:
This is from an unusual staged production, but it is the singing that is important. Going back to the song by Tom Waits, I understand the siren call of this kind of music for a classical performer. For years I have wanted to do a couple of Bob Dylan songs in a concert. With a singer I have done McCartney's "Blackbird" which, with a little pre-recorded birdsong, we were able to reproduce pretty accurately. But as I think we can hear with Boesch's version of Tom Waits, this is an urge that should normally be resisted. Not to say that there might not be an occasion when this could work, but as a rule, no. A singer trained for many years to sing lieder and opera is going to sound weird and awful singing this kind of music. Why? Song-writer performers like Tom Waits, Leonard Cohen and Bob Dylan have each a unique personal style of singing that they have developed and write specifically for. Often one kind of singer will 'cover' a song by another, and sometimes this can work well. Here, for example, is Jennifer Warnes doing the Leonard Cohen song "Bird On A Wire":
But you still need to hear the original version:
I think that works because Jennifer Warnes has made a specialty of Leonard Cohen and worked closely with him.
The reasons why a performance might be misconceived or just go awry are some of them simple and some of them complex. Let's take the simple ones: a classical musician can misunderstand the performance practice. Let's say the original song has some odd pitch fluctuations that, to the classical singer, sound out of tune. That they may be. But this kind of out-of-tuneness might be a part of the style, as it is with, say, blues singers. Just singing the occasional note randomly out of tune, though, is not good performance practice! You really have to immerse yourself in the style. It goes both ways, of course. A blues guitarist playing Bach might do some slides and note bends that are just wrong for the style. Performance practice is a subtle thing. All different kinds of music have their own performance practice.
When a classical artist decides to do some popular music (is Tom Waits actually 'popular'?) they often do not immerse themselves deeply in the performance practice. For popular music it is often difficult to do because the methods by which one learns, for example, to sing early 17th century monody (study of the repertoire, texts on performance practice, ornamentation, etc.) are not going to work for Tom Waits as some of his performance practice is based on the quality of his own voice and none of it is written down. It is easier for Sting to do John Dowland, though the results may not be any better.
It boils down to, if you step outside the genres and styles you have spent all your formative years studying, you are less likely to hear the ways in which you are getting the style wrong.
There are more complex reasons why this kind of thing usually goes wrong. The whole aesthetic context of Handel or Bach is so utterly different from the context of Tom Waits or Leonard Cohen, that the idea that one person could do both well is nearly inconceivable. Just try and imagine Tom Waits singing Handel! See what I mean? He has the sense to never try. But because his music is, in simple technical terms, accessible to a classical singer, it can seem like an easy thing to do. It is not.
I promise to continue to refrain from doing a version of "All Along the Watchtower" in my next classical recital. So you can all heave a sigh of relief...