1 Buddha, above all else, I would LOVE to smoke with him and have a good conversation. (btw, just for clarification, "Buddha" means "enlightened one". his actual name is Sidhartha Guatama).

otherwise:

2. Jimi Hendrix

3. EDIT: will have to agree with the above post and go with Dave Chapelle.

4. Singer from IN FLAMES (forget the name at the moment)

5. Tarja Turunen (singer from nightwish).