This question occurred to me as I looked at some previous presidential elections. Did you know, for instance, that the Nixon-Humphrey race was very close? It was, at least in the popular vote count: 31.8 million votes for Richard Nixon, 31.3 million for Hubert Humphrey. But Nixon won the electoral college in a blowout: 301 to 191. The native Californian won that state as well as other population centers such as Illinois and Ohio while losing Texas (oh how times have changed in 40 years). But he ran up the score on Humphrey by winning a bunch of small-population states that had more electors than they "deserved" if it was based on population alone.
Barack Obama looks to be headed for 365-273173 win in the electoral college assuming John McCain takes Missouri and Obama takes that Omaha elector. Does that margin fairly represent Obama's win? If, instead of giving a state the number of electors equal to their number of Senators plus House members, we apportion 538 electors based purely on current population what happens? I did this using 2007 state population figures and found the result would be this:
Obama 374, McCain 164
So the answer to the question in the title of the post is "yes" but only a little. The reason is that in the current system both McCain and Obama win small states that are "over electored." For example, McCain wins WY, ND, SD, and AK which really deserve only one elector (by population) while Obama wins DC and Vermont which would be in the same category. McCain won more of these small population states but not enough to significantly alter the electoral outcome.