For posterity, if you are hitting a data specific error, you can throw some debugging code in the script to see which records are giving you problems. In this case, you could pass in the ObjectID to the field calculator function and put it in and arcpy.AddMessage note. This way you would see how far things get before hitting the error.
def rand_num(): import random return random.randint(1,100)
(yourField) = rand_num()