So I've been doing some math because I have seen some bad math here.
To calculate the voting power of any individual electoral vote, it's a bit more complicated than the Population (P) divided by the total electoral votes (E).
This is because each state gets 2 electoral votes automatically. All remaining votes are given to match the number of House of Representatives allocated to that state. So, it's incorrect to say the electoral vote is equal to P/E because 2 of those votes represent the entire population of the state.
It is better to say that when someone votes for the president, their votes are used to determine 3 votes, not one. So if we have a unit called Representative Power (R) of a single Electoral vote for a given state, then our formula becomes:
R = (((P/(E-2) + (2P))/(E-2)))
Thus given the numbers set by @LeeDanielCrocker, let's first see what R of Califorinia would be:
Let P = 39,250,00 and E = 55
Thus our equation comes to:
R(CA) = (((39,250,00/53) + 2(39,250,000))/53)
R(CA) = ((740,566 + 78,500,000)/53)
R(CA) = 79,240,566/53
R(CA) = 1,495,105
So, with that in mind, we can now calculate Wyoming using the same numbers:
Let P = 585,000 and E = 3
R(WY) = (((585,000/(3-2)) + 2(585,000))/(3-2))
R(WY) = 585,000 + 1,1700,00
R(WY) = 1,755,000
So the R(WY) is definitely greater than the R(CA).
In fact, one California electoral vote equals 82% of one Wyoming vote. But this is on a one to one voting weight only. No matter how you slice this though, 3 votes at 100% power is still less than 55 votes that represent 82%.
So there is the math behind the idea of the smaller the total electoral votes the more powerful your vote becomes. This would be true of the force behind a Congressional seat as well.
This is a result of what is called the Great Compromise. As a Representative Democracy, figuring out how citizens would be represented in Congress needed to be a balancing act. If each state got an equal number of votes, small states could impose their will on large states because their vote is equal to the hundreds of thousands, while the larger state's vote is in the 10s of millions. Conversely, if they were given out by population, then the large states would be more powerful than the small states, because their vote is worth the same, but they have 55 times more votes than the smallest ones.
The balance here was to allocate 2 votes to every state and additional vote for each division of population. This makes it that small states have more powerful votes but large states have more numerous votes.
To understand the electoral college's design, think of each state as an individual country and the Federal Government as a big treaty organization between all of the member states. The leader of this organization would in effect be the leader of all the states. So it was necessary to pick the leader that showed he had the best interests of the individual states in mind. Hollywood actors and Oklahoma corn farmers have very little in common and very different needs from government. Each state does have its own interests to look out for.
Since each state is entitled to pick its representation in the way it sees fit, provided that it is a Republic (read representative democracy which was how the framers understood it), then the balance is that each state is afforded a share of votes equal to their congressional delegations (2 + the House Delegation). They are free to distribute them however they see fit (mostly winner take all; two states delegate the districts to the winner in that district and the remaining two to the overall state winner, and South Caroline historically voted on the full delegation in the legislature; and a number require by law that electors vote for the candidate the state chose). However, the states are only given so many votes in accordance with their congressional power.
The most balanced option is to distribute like Maine and Nebraska (congressional districts determine all but 2 of the electoral vote, and the 2 remaining are given to the winner). This would get us closer to the popular vote but we would still run into an occasional popular/electoral split.
Now, before you say this is undemocratic, consider this:
Switzerland is the world's only Direct Democracy and is, with notable exceptions, modeled after the United States Federal System. Switzerland does give its people the right to directly write and repeal their laws and even amend their constitution (with exception to citizens rights, which cannot be repealed from the constitution). In order to pass in this method, the law must pass with Double Majority. This means that popular vote alone does not get the job done, the law must achieve popular support in a majority of the Cantons (basically the same thing as States) in order to pass. A popular/Canton split means the law is not valid. This check is intended to avoid the tyranny of the majority like the electoral college was in the United States. Double Majority is a little hard to do in the United States Presidential elections because there is no proposal as to what would happen if a Double Majority is not achieved on a leadership position. Swiss got around this by making an Executive council of seven co-equal executive members, with each one rotating into the Council President and Vice President, who would be the de facto leader in a diplomatic settings. This committee is appointed by the legislature, not election of the people, so even in one of the most Democratic nations in the world, the people do not get to directly pick their top leadership by popular vote.