One thing I always wonder about regarding this interesting exercise is the chemistry between the guests themselves. Did you factor this into your choices, Paul? Or does one just pick five people they'd like to meet? I wonder if there's going to actually be a conversation or just awkward silence. Or maybe Cecil, Louis and Duke end up hanging in the kitchen while Ives and Bach sit at the table (although if Louis brings some weed that could get things loosened up). I think Bach and Bird would be interesting. Or Debussy and Bill Evans. Or Stravinsky and Gil Evans.
With Paul's particular group it would be interesting to have a piano around.