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I'm pretty sure this would change a lot depending on the bourbon. I used Turkey 101 and thought it was great, will go with Old Grand Dad 114 next to try something with higher rye content
Mine was Benchmark Old No. 8, Savory & James Amontillado, Amaro Nonino, Giacomo Sperone Vermouth di Torino. I picked something different for the Sherry, as Lustau Los Arcos didn't have great reviews.
Is a DRY Sherry the key?
Perhaps I hit a trifecta of mediocrity, but this didn't really do much for me.