James Monroe is an interesting dude. A little too young to be completely effectual as a founding father, he often gets overshadowed by his predecessors, particularly his mentor, Thomas Jefferson. And sure, that Missouri Compromise business was a pretty huge misstep. But look at what he did do - he acquired Florida, he penned the Monroe Doctrine, and he deemphasized partisan politics. Which was kind of a no-brainer given that Federalism was pretty much dead by this point, but still. People liked him quite a lot. He was the only president other than George Washington to run unopposed for re-election, and he won the 1820 election practically unanimously.
I say practically because there was that one guy in the Electoral College who just had to be a hater. William Plumer of New Hampshire, a staunch Federalist, couldn't bring himself to vote for Monroe. Instead, he cast his vote for Monroe's Secretary of State, John Quincy Adams. Interestingly enough, JQA's own father didn't vote for him, most likely because JQA wasn't actually intending to run and Plumer's vote kind of came out of nowhere...still, it's interesting that the one voice crying out in the wilderness on his behalf was not his dad.
JQA stepped right up to the plate voluntarily as soon as Monroe was done with this President stuff, and in the 1824 election Dad was more than happy to back him up. Most folks preferred Andrew Jackson, on the popular as well as electoral side, though, and it was only after a lot of heated contention that JQA pulled that victory out. (Surely I can't be the first person to feel a little deja vu when it comes to this tale of the son of a former president running away with an election after he lost the popular vote.)
Okay, maybe that's not funny ha-ha so much as funny strange. Still.