Will airport security check files on External Hard-Drives and laptops?

Despite the fact that almost everyone is against using profiling in performing security checks, I think it is used today. So my answer would be, it depends on your profile. If you are just Mr. Average Joe, minding your own business, doing nothing to compromise the well-being of others and not engaged in any illicit activity, then you should be fine. However, if you happen to fit a certain profile that is on the watchlist, chances are good that you will be inspected thoroughly. But that's just my opinion.