Originally Posted by Caao

That really depends. If you are unemployed right after school, first few months can be explained away by searching in progress. Once it hits 6 months it becomes downhill all the way as employers are usually cautious and wonder why you cannot find anything for so long.

As for contractor it depends on the type of industry. Banking BO and IT industry is quite common, so if you stay within the industry employers tend to be more understanding. It's not fantastic from a CV point of view, but at least acceptable if the first 3-4 years is contractor. Anything beyond 5 years still in contract then I think is not good.