Websites
You know you're important when you've got your very own international society. It's got information, documents, even myths about the man.
Pretty much exactly what it sounds like. A one-stop shop for all things Churchill, including photos, a timeline, and quotes.
No, he never went there, but plenty of actors have portrayed him. Here's some of the more famous ones.
The Miller Center's a great source of information about major figures in American political history. The section on FDR, especially the part about Foreign Affairs, helps you understand the larger context of World War II, especially if you just can't manage without having the American perspective. FDR and Churchill were great buddies, btw.
Movie-TV-Productions
We'll watch pretty much anything with Colin Firth in it (hellooo Mr. Darcy), but the fact that he won the Oscar for this one is a testament to how good it is. Oh, it also won Best Picture, which is apparently a big deal. Anyway, it tells the story of King George VI learning to speak publicly with a stutter, focusing on the couple years leading up to his speech announcing the declaration of war with Germany. Churchill only makes a brief appearance, but you can't have it all.
Although the title is taken from Churchill's own book about World War II, this TV movie was focused on Churchill and his wife, Clementine. Just in case you want to get a little more insight into his personal life. It stars Albert Finney and Lynn Redgrave, two acting legends—you can't go wrong with those guys.
Also based on Churchill's book, this TV movie looks at the war years.
John Lithgow is awesome as Churchill in this 2017 Netflix series about the early days of Queen Elizabeth II's reign.
A documentary film that asks the question: What if the world had listened to Churchill's warnings about Hitler?
Articles-and-Interviews
There are surprisingly few interviews with our guy, and this one goes way back to when he was First Lord of the Admiralty (the first time), during World War I. Not surprisingly, there's a lot about the British Navy in there.
You gotta figure that a major change in leadership in a country like Great Britain has to make the news. Well, it did, as did that little speech he gave—something about sweat and tears?
New Yorker essayist Adam Gopnik writes 70 years after Churchill's other famous wartime speech about Churchill's background, his supporters and detractors, and what made him a master speechmaker in 1940.
Video
Here's a clip from the recent Netflix series The Crown, in which John Lithgow plays Winston Churchill pretty fabulously during his second tenure as prime minister.
Here's video footage of Churchill giving a speech to the U.S. Congress in 1942. Always fun to see the real people—plus you see how he charms the crowd.
If you can't get enough Winston, here's a 4-hour documentary about him, including lots of video from throughout his life.
Audio
Thanks to the invention of recording technology, we can actually hear all these famous World War II-era speeches. You get to hear all those wonderfully posh British accents.
Since this is probably the most famous of Churchill's speeches, it can't hurt to give it a listen. We promise, it won't hurt.
Images
This is one of the most iconic images of Churchill, taken in 1941.
Here's Chamberlain holding up the Munich Pact, which he had just signed with Germany. Monty Python said it took second place on the list of "the world's funniest jokes."
BFFs…even dressing alike.
WC, FDR, and Stalin deciding the fate of the world. Really.
Here's our guy reprising his speech to Parliament for the BBC.
Churchill's portrait on the cover of Time when he was named "man of the year," although he'd be on the cover several other times.
Yup, that happened because of the Munich Pact. They explained their choice by saying, "Hitler became in 1938 the greatest threatening force that the democratic, freedom-loving world faces today.".