Did he live to be over 90?
Not Jimmy Stewart.
Did not live to 90 years old.
Was he a naturalized citizen of the US?
If this is 20-Questions, why limit to guys?
And, PS, games like this belong more in MPSIMS than in Cafe Society. I’ll let this one slide, since it’s about an entertainer.
I will guess Frank Sinatra.
It’s not Twenty Questions, it’s Dead Guy in the Envelope! You can move it where it belongs, CK. The next dead guy might not be in entertainment. Sorry about that.
ok-
Not Frank Sinatra.
Born in USA.
Was he a comedian?
Technically, you gave more away with that born in the USA answer then the question actually asked. 
Was he a actor?
Nope.
Recap: Entertainer, US citizen, lived in 20th century, over 65 at death but not 90, not a comedian.
You guys are going too fast for me! 
Warning - I’m leaving work (hehe) in 30 minutes, and there will be a short intermission until I get home.
Ok - (I wasn’t sure what naturalized meant! Oh well.) Yes he was an actor, no he wasn’t a comedian.
Was he alive 5 years ago?
Yes.
Did he die since 2000?
Was he a good golfer?
Was he Bob Hope?
sorry, I’ll think of a new one.
Yes, he died since 2000. (That sounds grammatically incorrect…hmm.)
Not known for golfing - he might have though. Not Bob Hope.
Marlon Brando?
Not Marlon Brando.
Was he on TV?