The U.S. Census Bureau will let anyone download their datasets. There is some cool stuff here. Did you know they keep track of the population of every city and town?
I did a little crunching in Excel. 16385 of 19494, or 84.0%, of the areas they track had less than 9000 residents in 2007 (in Wisconsin, 504 of 592, or 85.1%).
Granted, the population totals break down 26554516 to 161695447 (the 300M figure must include a lot of fudge factors for underreporting illegal aliens and others who don't fill out their form...), or 16.4% of the population lives in towns under 9000. But a whole lot of city folk came from somewhere small, or their parents did, and they're not all self-loathing hipsters ashamed of their backgrounds...
I can't believe no one on O's staff knows these things, and/or cares enough to tell him to shut up about the small towns already (yeah...now it's personal).