Currently living it would be Rinella at his SE Alaska Cabin or Remi Warren in New Zealand. From years past it would be sheep with Jack O'Connor or Africa with Robert Ruark.
But, I would trade any hunt with any of those guys for one last coon hunt with great grandfather in the river bottoms of his old farm.
Boggles my mind how many guys/gals would want to hunt with these TV personalities more than anyone else. To me - family that have passed, people in history (old mountain men, native americans, etc) would be way more memorable than Rinella or Newberg. Just cracks me up