How Many Times Paint Number 9 John has been hired to paint the numbers 1 through 100 on 100 apartments. How many times will he have to paint the number 9? Answer 20 times. They are 9, 19, 29, 39, 49, 59, 69, 79, 89, 99 (2 times) followed by 90, 91, 92, 93, 94, 95, 96, 97, 98. « Previous Riddle9 and 5 Is 13 or 9 plus 5 Is 13 Next Riddle »Horse on a 24 Foot Chain