Raggedy got it - Karl Malden. Sorry for the delay...
Richard Nixon
Ralph Nader
Not:
Richard Nixon
Ralph Nader
Randy Newman?
Rick(y) Nelson?
Not:
Richard Nixon
Ralph Nader
Randy Newman
Rick(y) Nelson
Rudolph Nureyev?
Female? Living? Real?

Rudolph Nureyev is correct.
American?
Hugh Hefner
Harry Houdini
Holly Hunter
American
HH
not Hugh Hefner
not Harry Houdini
not Holly Hunter
Hubert Humphrey
Howard Hughes
Howard Hawks
American
HH
not Hugh Hefner
not Harry Houdini
not Holly Hunter
not Hubert Humphrey
not Howard Hughes
not Howard Hawks
Real living American male
not Hugh Hefner
not Harry Houdini
not Holly Hunter
not Hubert Humphrey
not Howard Hughes
not Howard Hawks
Real living American male
not Hal Holbrook
not Hugh Hefner
not Harry Houdini
not Holly Hunter
not Hubert Humphrey
not Howard Hughes
not Howard Hawks
Real living American male
In entertainment
not Hal Holbrook
not Hugh Hefner