I'm not actually sure that Oliver's premise is correct, that people would be substantially more outraged if they understood their nudes were being seen by the NSA. In fact, we've had this exact debate before re: body scanners in airports. In those cases, people make the connection: while it's obviously preferable to retain that privacy, if the very serious and important trained agents need to do this to stop their plane from blowing up, they're OK with a little bit of exposure.

Really this all turns on the degree to which the individual believes the government usually acts within the interest of the population. If you think the government is a good institution and that they are honestly just interested in national security, you'll accept your "dick pics" becoming collateral damage. If you believe that the government or one of its [former] operatives may use that information against you one day, you won't.