In the land of the free, it is possible to win the popular vote and lose the electoral vote, and therefore the election. It is also possible to win the election with less than 50% of the voting population. Both of these scenarios, as well as others, have happened in actual elections.
There have been 12 Presidential elections that were decided by less than a 1% margin; meaning if less than 1% of the voters in certain states had changed their mind to the other candidate the outcome of the entire election would have been different.
Case and point: in 2000, if only 269 Floridians had voted with their heads instead of with their ass (or if the hanging chad issue hadn’t stolen the election), Al Gore would have won the election and the Dubya era would only have been a bad what-if scenario.
Source: https://www.msu.edu/~sheppa28/elections.html#2004