Apprentice Guru
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Probably the most successful has been Danny Elfman, from Oingo Boingo. He's composed the Simpsons theme, as well as scored most of Tim Burton's films (Batman, Edward Scissorhands, etc.)
One important thing to note is a lot of these crossover composers don't *orchestrate* their own music. I know Elfman didn't, at least as of several years ago, and neither did McCartney. This may have changed recently, I'm not sure.
I don't doubt they had major input in the orchestration of their works, but still, orchestration is an art in itself. This makes their classical ventures a little less notable for me, at least.
I imagine the collaboration between crossover composer and orchestrator finds the orchestrator saying things like, "No, that melody's too low for violin, how about viola? Don't like that? OK, how about bassoon? No? Well, we could bring it up an octave to violin range, but then we'd have to re-do this pedal chord, perhaps this way...no good? Well, here's another option..." etc. etc. That's a generalization, I know, but it seems like however you slice it the orchestrator is doing a large amount of the work.
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