Were you a painter who was close friends with JFK and Jackie Kennedy? - Not Andy Warhol (too early, pretty much), but William Walton
Were you a big Nixon donor who became ambassador to the Court of St. James’s? - Walter Annenburg
Did you succeed Fred Vinson in a big job? - Earl Warren, as Chief Justice of the United States
Guns, because only a stereotypical few types of characters usually carry them, and NYC, because it’s a common setting for books, movies, TV shows, etc., and its exclusion can rule a lot of things either in or out.
DQs:
First appeared in comics?
Associated with NYC?
Considered handsome?
IQs:
Are you Dilbert’s lazy but funny coworker?
Did Richard Cordray get a job that many thought you should get?
Did your character run through white-trash women’s names with a talking teddy bear?
Are you Dilbert’s lazy but funny coworker? - Yes, Wally
Did Richard Cordray get a job that many thought you should get? - Elizabeth Warren; Cordray and not she was appointed by President Obama to head the Consumer Finance Protection Bureau
Did your character run through white-trash women’s names with a talking teddy bear? - Yes, Mark Wahlberg (sp) (NSFW after 1:24): Ted (6/10) Movie CLIP - White Trash Names (2012) HD - YouTube
DQ:
Marvel character?
IQs:
Do some speculate that your middle name was Hamish?
Were you the young head of the Baker Street Irregulars?
Did you play Stapleton in a movie adaptation of The Hound of the Baskervilles?
IQ1: Are you a bandleader who was married to Charo?
IQ2: Are you a pro wrestler who is a member of New Day?
IQ3: Does Nicholas Brendan play you in Buffy the Vampire Slayer?
Do some speculate that your middle name was Hamish? - Dr. John H. Watson
Were you the young head of the Baker Street Irregulars? - Wiggins
Did you play Stapleton in a movie adaptation of The Hound of the Baskervilles? - William Shatner
On to X…
IQs:
Was your fleet defeated at the Battle of Salamis?
Did you play a turncoat Secret Service agent?
Were you Luna Lovegood’s papa?
iQ1: Does the bard Gabrielle help you stay on the good path?
IQ2: Were you a mistress of the Toltec Emperor Tecpancaltzin?
IQ3: Are you an ancient Greek historian who chronicled the last years of the Peloponnesian War?