Correct on the first and third. The second is the title character of Roald Dahl's novel My Uncle Oswald (his girlfriend joked that it was because "it's a whale of a ship!").
Oswald x3!
DQ:
Real?
IQs:
Were you Mork's boss?
Were you the most noteworthy descendant of Lincoln's SECNAV?
Were you a voice actor in the TV animated adaptation of The Hobbit?
Were you Mork's boss? - Orson, on Mork and Mindy
Were you the most noteworthy descendant of Lincoln's SECNAV? - Orson Welles, a grandnephew (or something) of Gideon Welles
Were you a voice actor in the TV animated adaptation of The Hobbit? - Orson Bean, recently tragically killed by a car while crossing an L.A. street
Orson x3!
DQs:
Male?
American?
Living?
IQs:
Were you the longtime conductor of the Philadelphia Orchestra?
Did you lead the Freedmen's Bureau after the Civil War and later have a college named after you?
Are you the meanest being on Sesame Street?
Were you the longtime conductor of the Philadelphia Orchestra? - Yes, Eugene Ormandy
Did you lead the Freedmen's Bureau after the Civil War and later have a college named after you? - not Mr. (actually Rev.) J.F. Oberlin, who never came to the U.S., but Gen. O.O. Howard
Are you the meanest being on Sesame Street? - Yes, Oscar the Grouch
DQ:
European?
IQs:
Were you Charlie Chaplin's daughter?
Did you make a cameo appearance on the street in Dave?
Were you named one of the top mayors in the country by Time magazine before being elected governor of your state?
Were you Charlie Chaplin's daughter? - Yes, Oona Chaplin
Did you make a cameo appearance on the street in Dave? - Orrin Hatch wasn't in the movie - this was Tip O'Neill
Were you named one of the top mayors in the country by Time magazine before being elected governor of your state? - Martin O'Malley of Baltimore, Md.
DQs:
From the British Isles?
First name start with O?
IQs:
Were you the subject of a great Russian work of fiction?
Did you say "I have done the state some service, and they know it"?
Were you the villain in several early Star Trek fanfic books?
Were you the subject of a great Russian work of fiction? - Heh. Dr. Zhivago's first name was Yuri; I was thinking of Eugene Onegin
Did you say "I have done the state some service, and they know it"? - Othello
Were you the villain in several early Star Trek fanfic books? - Omne
DQs:
English?
Political/military?
Died since 1900?
IQs:
Did you tell a painter to capture your likeness "warts and all"?
Were you a British Army officer who became an early Israeli hero?
Did your wife die on 9-11-01?
Did you tell a painter to capture your likeness "warts and all"? - Oliver Cromwell
Were you a British Army officer who became an early Israeli hero? - Orde Wingate
Did your wife die on 9-11-01? - Yes, Ted Olson
DQs:
Held a noble title or knighthood?
Best known for politics?
IQs:
Were you an American poet known for light verse?
Were you a plump American TV journalist and host?
Were you a young Wildling woman who helped Bran Stark?
1.Real
2.Male
3.Dead
4.NOT American
5.European
6.From British Isles
7.First initial "O"
8.English
9.Political/Military
10.Died AFTER 1900
11.No noble title, never became Sir
12.Political figure
"Held a noble title or knighthood?" was a single question that could have been answered either "yes" or "no." I respectfully suggest that you did not have to break it up and answer it as two questions, and thus take away one of my future questions.
Previous IQs:
Were you an American poet known for light verse? - Yes, Ogden Nash
Were you a plump American TV journalist and host? - Charles Osgood
Were you a young Wildling woman who helped Bran Stark? - Osha, in Game of Thrones
DQs:
Served in the House of Commons?
Died after 1945?
IQs:
Did a movie show you, dressed to the nines, descending into a coal mine?
Did your sister Katherine serve on the Oberlin College board of trustees?
Were you a favorite designer of Jackie Kennedy's?
1.Real
2.Male
3.Dead
4.NOT American
5.European
6.From British Isles
7.First initial "O"
8.English
9.Political/Military
10.Died AFTER 1900
11.Earned noble title, was also Knighted
12.Political figure
13.Served in House of Commons
14.Died AFTER 1945
Did a movie show you, dressed to the nines, descending into a coal mine? - Oscar Wilde
Did your sister Katherine serve on the Oberlin College board of trustees? - Orville Wright (the physics building is named after the family)
Were you a favorite designer of Jackie Kennedy's? - Yes, Oleg Cassini
DQs:
Conservative?
Was Prime Minister?
IQs:
Did you play Burt Wonderstone's girlfriend?
Did you costar in Captain Blood?
Did you win an Oscar for Moonstruck?
1.Real
2.Male
3.Dead
4.NOT American
5.European
6.From British Isles
7.First initial "O"
8.English
9.Political/Military
10.Died AFTER 1900
11.Earned noble title, was also Knighted
12.Political figure
13.Served in House of Commons
14.Died AFTER 1945
15.STARTED a Conservative
16.NEVER became PM
Did you play Burt Wonderstone's girlfriend? - Olivia Wilde
Did you costar in Captain Blood? - Olivia de Havilland
Did you win an Oscar for Moonstruck? - Yes, Olympia Dukakis
DQs:
Served as any of the following: Chancellor of the Exchequer, Foreign Secretary, Home Secretary?
Ended his career in the Labour Party?
IQs:
Were you the young protagonist of the animated film The Point?
Did you use a trick-of-the-eye artwork to help people find common ground?
Were you a police officer mentioned in an Arlo Guthrie song?
1.Real
2.Male
3.Dead
4.NOT American
5.European
6.From British Isles
7.First initial "O"
8.English
9.Political/Military
10.Died AFTER 1900
11.Earned noble title, was also Knighted
12.Political figure
13.Served in House of Commons
14.Died AFTER 1945
15.STARTED a Conservative
16.NEVER became PM
17.Never held ANY of those offices
18.While in Labour along the way, did NOT finish as member of Labour Party
Were you the young protagonist of the animated film The Point? - Oblio
Did you use a trick-of-the-eye artwork to help people find common ground? - Rev. J.F. Oberlin, namesake of the college: http://www.oberlinlibstaff.com/omeka_oca/items/show/180
Were you a police officer mentioned in an Arlo Guthrie song? - Office Obie, in "Alice's Restaurant"
1.Real
2.Male
3.Dead
4.NOT American
5.European
6.From British Isles
7.First initial "O"
8.English
9.Political/Military
10.Died AFTER 1900
11.Earned noble title, was also Knighted
12.Political figure
13.Served in House of Commons
14.Died AFTER 1945
15.STARTED a Conservative
16.NEVER became PM
17.Never held ANY of those offices
18.While in Labour along the way, did NOT finish as member of Labour Party
19.Died BEFORE 2000
20.NOT known for singular incident
21.Never in Cabinet (much to his disappointment)
How about 2:30 PM Sunday ET for your guess (2:30 AM Saturday as I type)
Were you a former Arizona governor who served in the Clinton Cabinet?
Do all of the members of the Philosophy Department of the University of Wollamaloo seem to have this first name?
Has this name long been (mistakenly) thought to have been sung in the original release of ELO's "Don't Bring Me Down"?
Were you a former Arizona governor who served in the Clinton Cabinet? - Yes, Bruce Babbitt
Do all of the members of the Philosophy Department of the University of Wollamaloo seem to have this first name? - Bruce:
Has this name long been (mistakenly) thought to have been sung in the original release of ELO's "Don't Bring Me Down"? - Yes, Bruuuuce!: https://en.wikipedia.org/wiki/Don%27...Misheard_lyric
Bruce x3!
DQ:
Real?
IQs:
Did you fall off an outdoor stage in your last political campaign?
Did you fake an assassination attempt against yourself?
Have you played a Soviet official, a pirate, a detective and a gangster?
Did you fall off an outdoor stage in your last political campaign? - Yes, Bob Dole, poor guy, in 1996
Did you fake an assassination attempt against yourself? - The title character in the political satire Bob Roberts
Have you played a Soviet official, a pirate, a detective and a gangster? - Bob Hoskins, in Enemy at the Gates, Hook, Who Framed Roger Rabbit and The Long Good Friday
Bob x3!
DQs:
Male?
Last name start with B?
IQs:
Have you played a network executive, a concierge, a computer expert and a Federal prosecutor?
Did you once pretend to be a PR guy advising Lincoln on his Gettysburg Address?
Did you semi-commit to naming your son after a baseball player?