Jack Black IS a musician, like it or not.

Charles Bukowski did some spoken word... so... that won't qualify will it? ****.

But.
Janis Joplin would've been fun to drink with. Morrison (but then, Meg Ryan would cut me with knives, Joli style n'awl...)
Bob Dylan. ****. That'd be interesting.
Lou Reed, after watching Prozac Nation. That'd be interesting. "Let's face it, Lou Reed should be dead." Ha.

But Keith Richards has to win. Because... he's Keef. And I have an unlogical devotion to him and Mick.

/I'm***.
And I also quit drinking.

Maynard James Keenan. I would be very scared but it would be very interesting.

Brian Eno.