see: http://fivethirtyeight.com/features/how-high-can-count-von-count-count/

thecount.py

word_map = {
	"1": {
		"0": "",
		"1": "one",
		"2": "two",
		"3": "three",
		"4": "four",
		"5": "five",
		"6": "six",
		"7": "seven",
		"8": "eight",
		"9": "nine"
	},
	"2": {
		"1": {
			"0": "ten",
			"1": "eleven",
			"2": "twelve",
			"3": "thirteen",
			"4": "fourteen",
			"5": "fifteen",
			"6": "sixteen",
			"7": "seventeen",
			"8": "eighteen",
			"9": "nineteen"
		},
		"2": "twenty",
		"3": "thirty",
		"4": "forty",
		"5": "fifty",
		"6": "sixty",
		"7": "seventy",
		"8": "eighty",
		"9": "ninety"
	},
	"3": "hundred",
	"4": "thousand",
	"7": "million",
	"10": "billion",
	"13": "trillion",
	"16": "quadrillion",
	"19": "quintillion",
	"22": "sextillion",
	"25": "septillion",
	"28": "octillion",
	"31": "nonillion",
	"34": "decillion"
}


def expansion(n,b):
	q = n
	k = 0
	a = []
	i = len(str(n))

	while q != 0:
		a.append(q % b)
		q = q / b
		k += 1

	return a

def expand_base_10(n):
	return expansion(n,10)

def say_number(n):
	tens = expand_base_10(n)
	return say_number_recur(tens, len(str(n)))

def say_number_one(tens, ret_val=''):
	if tens[0] != 0:
		ret_val += word_map["1"][str(tens[0])]
		return ret_val
	return ''

def say_number_two(tens, ret_val=''):
	if tens[1] == 0:
		return say_number_one(tens[0:len(tens)-1], ret_val)
	if tens[1] == 1:
		ret_val += word_map["2"]["1"][str(tens[0])]
		return ret_val

	ret_val += word_map["2"][str(tens[1])] + say_number_one(tens[0:len(tens)-1], ' ')
	return ret_val

def say_number_three(tens, ret_val=''):
	if tens[2] == 0:
		return say_number_two(tens[0:len(tens)-1], ret_val)

	ret_val +=  say_number_one(tens[len(tens)-1:len(tens)]) + ' ' + word_map["3"] + say_number_two(tens[0:len(tens)-1], ' ')
	return ret_val

def say_number_recur(tens, num, ret_val=''):
	if num == 1:
		return say_number_one(tens, ret_val)
	if num == 2:
		return say_number_two(tens, ret_val)
	if num == 3:
		return say_number_three(tens, ret_val)
	if tens[num-1] == 0:
		return say_number_recur(tens[0:len(tens)-1], num - 1, ret_val)

	ret_val += say_number_recur(tens[len(tens)-(num%3 or 3):len(tens)], num%3 or 3) + ' ' + word_map[str(num - (num%3 or 3) + 1)] + say_number_recur(tens[0:len(tens)-(num%3 or 3)], num - (num%3 or 3), ' ')
	return ret_val

def pad(num, length):
	strnum = str(num)
	while (len(strnum) < length):
		strnum = '0' + strnum
	return strnum


# configurable limit
limit = 139

# longest = 0
# longlength = 0
# for i in range(1, 1000):
# 	length = len(say_number(i))
# 	if length > limit:
# 		print i
# 		print say_number(i)
# 		print length
# 		break
# 	if length > longlength:
# 		longest = i
# 		longlength = length
# # longest 3-digit is 373

num = 373
while len(say_number(num)) <= limit:
	num = int(str(num) + str(longest))
	if len(say_number(num)) > limit:
		break
for i in range(1,999999):
	newnum = int(str(pad(i,6)) + str(num)[6:])
	length = len(say_number(newnum))
	if length > limit:
		print newnum
		print say_number(newnum)
		print length
		break

# # limit = 139
# 1111373373373
# one trillion one hundred eleven billion three hundred seventy three million three hundred seventy three thousand three hundred seventy three
# 140