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Answer:
MONROE
Possible Questions:
Fifth president
"Some Like It Hot" star
President with a doctrine
Presidential surname
Fifth U.S. president
Washington : 1 :: ___ : 5
Norman Mailer subject
Marilyn with a mole
Madison's successor
Legendary blonde
James or Marilyn
Face on a $5,000 T-bond
Doctrine developer
DiMaggio's love
DiMaggio spouse
"The Misfits" co-star
'Some Like It Hot' star
''Some Like It Hot'' star
Wife of DiMaggio and Miller
The capital of Liberia is named after him
Seventh secretary of state
Secretary of War under Madison
Secretary of State under Madison
Secretary of state during the War of 1812
Screen legend Marilyn
President, 1817-1825
President No. 5
President nicknamed Last of the Cocked Hats
President after Madison
Only president besides Washington to run unopposed
One of the Louisiana Purchase negotiators
Missouri Compromise signer
Memorable Warhol subject
Marilyn, wife of DiMaggio
Marilyn who sang Berlin's "Show Business"
Marilyn of "The Seven Year Itch"
Marilyn
Mailer subject
Madison follower
Last president to wear a powdered wig
James __ (fifth U.S. president)
Hollywood's Marilyn
Her white dress billowed over a subway grate in "The Seven Year Itch"
Florida purchaser
Eponym of an African capital
Doctrine maker
Doctrine developer of 1823
County name in 17 states
Bill ___, the Father of Bluegrass
"Some Like It Hot" actress
"Niagara" star, 1953
"Niagara" star
"Last of the Cocked Hats"
"Happy birthday, Mr. President" coquette
"Era of Good Feelings" president
"Bus Stop" star, 1956
'Some Like It Hot' cast member