Thanks to their analogous symbolic roles, Webb and Obama have one more politically important and bizarre similarity: They appeal to the same voters, wine-track Democrats who come out in unprecedented droves to vote for a black man or a hillbilly white because they want their party to be bigger than themselves. While you'd expect Webb to attract poor, rural beer-trackers, in his 2006 Senate race he didn't do any better than the previous Democratic candidate had among Appalachian voters in southwestern Virginia; instead, he was propelled to victory by Northern Virginia suburbanites — Obama's base.
Is this true? I compared the results of Webb's 2006 Senate race to John Kerry's 2004 performance in Virginia. Overall, Webb did about 4.3 percentage points better than Kerry did (50.2 percent of the two-party vote compared to 45.9 for Kerry). In the counties and cities in the southwestern part of the state (essentially everything west of Roanoke), Webb did about the same, running about 4.8 points ahead of Kerry (44.4 to 39.6). In northern VA counties and cities near Washington DC, Webb ran about 5.8 points better than Kerry (61.1 to 55.3). The difference in the Webb-Kerry vote between these two regions is pretty small (1 percentage point), indicating that Webb did better both with Scots-Irish Appalachian whites and with Starbucks sipping DC suburbanites.
Here's a map that illustrates the point I made above. Bluer areas saw the biggest swing from Kerry to Webb.