Each word or phrase below can be associated with a number. These numbers have something in common, and in turn are associated with a particular group of people. Can you determine the numbers, what they have in common, and the people with whom they are associated?

FOR THE MONEY
TERRIBLE
HIGH
HANG
QUESTIONS
STATES
DRESSES

HINT and first answer:

ONE FOR THE MONEY
TERRIBLE TWOS
HIGH FIVE
HANG TEN
TWENTY QUESTIONS 
FIFTY STATES
(THE) HUNDRED DRESSES

Rest of answer:

The numbers correspond to US currency denominations, and feature the picture of a US President or Founding Father:

ONE - WASHINGTON
TWO - JEFFERSON
FIVE - LINCOLN
TEN - HAMILTON
TWENTY - JACKSON
FIFTY - GRANT
HUNDRED - FRANKLIN 

Credit:  NY Times Crossword - Sept. 1, 2013
John Farmer
PERSONS OF NOTE  (adapted)