This was harder than I expected, probably because I'm not a big music buff and didn't recognize many artists' names. I will admit I had some help. I also found it very frustracting that the 'similar artists' lists are not reciprocal.
So I connected R. Carlos Nakai (native american flute music) with Tony Bennett. The trick was finding a crossover from new age to jazz, which happened somewhere in the links from Kitaro to Tangerine Dream to Jan Hammer. Here's my lengthy chain:
R Carlos Nakai ~ Dean Evenson ~ Deuter ~ Gandalf ~ Kitaro ~ Tangerine Dream ~ Jan Hammer ~ Chick Corea ~ Joe Zaniwul ~ Horace Silver ~ Miles Davis ~ Nina Simone ~ Carmen McRae ~ Ella Fitzgerald ~ Mel Torme ~ Tony Bennett.