TASK DEFINITION: You will be given a trivia clue, and the category it belongs to. You should answer with the best answer that belongs in the category and is described by the clue. For simplicity, answers should be in all lower cased letters.
PROBLEM: Category: "TWO" 
Clue: It features Jefferson on the front & the signers of the Declaration on the back

SOLUTION: two-dollar bill

PROBLEM: Category: PRESIDENTIAL FACTS 
Clue: In 1919 this trustbuster's last words were "Please put out the light"

SOLUTION: theodore roosevelt

PROBLEM: Category: EMMY HISTORY 
Clue: Hug it out!  In 2006 Jeremy Piven won Best Supporting Actor for this HBO comedy

SOLUTION:
entourage