Python
answer = len('onetwothreefourfivesixseveneightnine')
len_1to9 = answer
answer += len('teneleventwelvethirteenfourteenfifteensixteenseventeeneighteennineteen')
answer += len('twenty') * 10 + len_1to9
answer += len('thirty') * 10 + len_1to9
answer += len('forty') * 10 + len_1to9
answer += len('fifty') * 10 + len_1to9
answer += len('sixty') * 10 + len_1to9
answer += len('seventy') * 10 + len_1to9
answer += len('eighty') * 10 + len_1to9
answer += len('ninety') * 10 + len_1to9
len_1to99 = answer
answer += len('onehundred') * 100 + len('and') * 99 + len_1to99
answer += len('twohundred') * 100 + len('and') * 99 + len_1to99
answer += len('threehundred') * 100 + len('and') * 99 + len_1to99
answer += len('fourhundred') * 100 + len('and') * 99 + len_1to99
answer += len('fivehundred') * 100 + len('and') * 99 + len_1to99
answer += len('sixhundred') * 100 + len('and') * 99 + len_1to99
answer += len('sevenhundred') * 100 + len('and') * 99 + len_1to99
answer += len('eighthundred') * 100 + len('and') * 99 + len_1to99
answer += len('ninehundred') * 100 + len('and') * 99 + len_1to99
answer += len('onethousand')
print(answer)