I agree with a lot of the previous posts, but fear conversation and interest would dwindle if substances in immoderate quantities came into the picture... well at least for me... and I guess it depends on how the conversation goes... might take the red pill depending on the promise of the rabbit hole...
So, I asked my wife, she said Stevie Ray Vaughn without hesitation.
I can't pick between:
Yo-Yo Ma - who is such a positive, creative force and a role model for impeccable musicianship, emotional expressiveness, and camaraderie among musical communicators, as well as Asian-Americans generally, and
Stevie Wonder - my all-time hero, representing what humans can achieve against multiple odds and still represent a beacon for others to strive for, musically and socially: a true American genius.
Maybe more later, as I think Dave Holland would be a really cool guy to hang with.