History was undoubtedly my worst subject in school -- I was never able to memorize names and dates -- and in the real world it's kind of embarrassing not knowing which King Henry did what, or what the deal was/is with the whole communism thing. I have a hard time keeping track of which World War was which, who was President during major US history events, did Napoleon take over Europe before or after the French Revolution (what was the French Revolution? I have no idea), why South Africa is so different from the rest of Africa, the difference between all the different "barbarian" invaders (Normons, Vikings, Mongolians). I mix up Vietnam and Korea, I couldn't tell you who Stalin or Gorbachev or Lenin were besides that they were involved in communism. Or which was first, the Vietnam War or the Korean War.
Given that I have a crappy memory, browsing Wikipedia articles doesn't help me in the long term. I find that stuff interesting, but there's way too much content and it doesn't stick with me. So I'm looking for a book or website that relates world history 101 in a way that I can understand and remember. Any recommendations for books, websites, films or "study" plans would be appreciated.
I think you have a pretty fundamental misunderstanding of the purpose of history. This is the perfect opportunity for you to rectify that. While those anecdotes are funny I believe you're missing the forest for the trees; you are focusing far too much on the details and little facts and dates. The purpose of history isn't to memorize names and dates. Yes I can tell you off-hand which French king did what and roughly when they reigned or what kinds of artillery the French used in WWI or what the names of major philosophers who led to the rise of the German national identity. However that's not the point of history and you don't read to memorize those they come organically through constant exposure to a subject you are passionate about.
The content doesn't stick with you because you're overloading yourself. You don't binge read a bunch of wikipedia articles of disjointed topics and call it a day. You're not going to read a single article on Louis XIV and suddenly and forever remember things about him. I literally have dozens of books on what I study and I still forget stuff all the time. It's why we keep the books we read and why we reread them. Yes I enjoy reading them but more than that you just forget things. You should not go into studying history with the expectation that once you read all these articles or watch these documentaries or read this world history book you read it once and you got those dates forever.
The best way to learn history is to find something, anything, that interests you and read that. Stick with that topic and read it. Dive into something that just absolutely fascinates you and don't give two shits about anything else. You think I know a lick about Egyptian history? Or Russian history outside of how it interacts with my study? I can't tell you a single thing about Chinese history. However if we talk about Franco-German history you bet your behind I can talk for days on it. You seem to be absolutely lost and while that's okay you should take some effort to hone, calm down. You don't need to know about the Henry dynasty or a bunch of US presidents or what the French revolution was or the Korean war and the theories of barbarism all at once. You don't even need to know any of these.
We here at /r/AskHistorians have an expansive book list. Linked here is a section on 'general histories' which is something you may be interested in. I assume you are from the United States so here is the section on the United States. Ultimately don't feel compelled to read U.S. history or general histories or whatever. Feel compelled to read what interests you and not to bother about knowing everything.
If you'd like to discuss this further feel free to PM me. I'd be glad to discuss your interests and maybe give you some more direction within the booklist or elsewhere.
This is a great book that will give you a really sound overview of world history. Plus it has lots of great pictures which, if you're a visual learner, will help you to hold on to the information better. I would suggest reading a section every night before you go to bed. The ritual will help you go to sleep, and giving your mind some space between concepts will help you to separate them in your memory.
Andrew Marrs book: 'A History of the World' is an excellent overview which manages to be concise without droning on and on about dates and weird names. Its a self-admitted 'Great Person' history of the world, dealing with the more exciting emperors and prophets which drove history so is much more of a gripping read than just googling Japan and reading a wikipedia article on the growth of Buddhist pottery among Japanese artisans in the early imperial period.
I think he also did a TV series of the same name which you might be able to find on the internet, as the book is pretty big and might be a pain to find outside of the UK. (though well written so that shouldn't be too much of a problem.)