I haven't quite figured out how to sing two different songs simultaneously, but I do find that certain songs work well in sequence, going right from one to the other with no pause. One pair I like to do together is "Copper Kettle," then vamp on the guitar for a moment or two, slowing the tempo and segueing into the slow version of "Moonshiner." There are many versions of "Moonshiner," but the words I sing are fairly close to the ones that Bob Dylan sings, but I learned it from Rolf Cahn in Berkeley in 1959. Another is "Pull Off Your Old Coat," that I learned from a Richard Dyer-Bennet record, then speed up a bit and segue into "Wayfaring Stranger," starting softly, swelling to full blast, then backing off and finishing softly. Both of these combinations work well. Don Firth
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