Nobody reads books, and for libs that do read books, they're just gonna read the new Obama book or something. You're asking someone to invest a lot of time reading when IMO the better thing to do is give them little snippets and ease them into it.
If you're gonna push something, please make a it a very short video or a podcast. And please be sure to gauge where they are. What I mean is that you don't want to be sending videos titled "how socialists need to organize in this day and age" or "why marxism-leninism is better than trotskyism" or whatever. You gotta understand, these libs think "socialism = red fash." So gauge the video/podcast and make sure it doesn't explicitly mention certain trigger words like "socialism" or "communism." A perfect example of something that doesn't, as many have said before, is Citations Needed. Even then, asking someone to listen to a 40+ min podcast is also a lot. Personally, for libs, I think short and to the point Majority Report clips are good. And if they want more, they can go from there.
Remember, we're still living in a world where entertainment value is something that you gotta consider, so if it can relate to pop-culture and subtly tie in leftist ideas without explicitly saying it, the better (Here's a good example relating to Star Wars and how droids are treated: https://www.youtube.com/watch?v=WD2UrB7zepo). You want them to come to realizations, not preach to them. When they want to find out more, they'll do it on their own or come to you for more recommendations.
This is something that I think the left needs to work on, i.e. some kind of "chart" that you can place different youtubers/podcasts on. This can be used as a reference after you've properly gauged where your lib friend/family/acquaintance is. For ex, if your friend is anti-police brutality but still thinks it's "bad apples," and they're kinda bro-ey, maybe a V*ush vid is good. If they're already on board with Sam Seder, then maybe push Michael Brooks (RIP).
Anyways, TL;DR please don't recommend books (b/c nobody reads), recommend short vids or podcasts and gauge where the person is before sending them some "death to landlords" shit.
Someone named queenjamie is recommending Majority Report. Hmmmmmm
But I actually agree. I tried to get my mom to read Manufacturing Consent and watch some hour-long theory video on YouTube. It didn't really go that great. She'd read a chapter of the book before losing interest. But I recommended Economic Update with Richard Wolff as something she should listen to while walking/exercising etc and she now supports his ideas of workplace democracy etc.
She loves CNN and knows like half a dozen of those anchors by name. One day, I started putting on Majority Report. At first she was completely put off by it but I wasn't trying to get her into it. I'd just put it on and watch it. Over time, she grew to enjoy it. She still watches CNN, but when MR goes live she also wants me to put that on. She likes the humor, finds Sam Seder funny, and thinks Emma Vigeland makes lots of goods points.
When the George Floyd protests were going on, she'd bought into the CNN narrative about looters and rioters and all that. I sent her dozens upon dozens of TikToks of police brutality and got her to realize the truth. Watching Cornel West and Nina Turner talk about "black faces in high places", learning how little Obama did for the black community, how BLM started under him etc. got her to change her view on Obama.
When the China trade-war was ramping up she proclaimed she'd never buy any Chinese product again. Went really hard into anti-China stuff, always saying how it's the Chinese government that's the problem not the people, obviously. Then Covid happened and she was completely on board with blaming China, and being disgusted with the Chinese people eating bats and their meat markets and everything. But, again, over time she's seen the response to Covid by China and literally the entire rest of the world. Even now none of the "democracies" have their shit together (other than small islands like NZ). Now she thinks China had the perfect response, doesn't mind buying Chinese commodities etc.
Radicalizing individuals is a long process. You have to push back against the propaganda, but not in an antagonistic way. You cannot browbeat them into chanting Death to America when all their lives they've thought of the US as the Land of the Free and the protectors of democracy. But when they are parroting the latest CNN propaganda about Kim Jong Un, you can counter it with the Korean War. Make them understand the historic conditions that forced AES states (Cuba, Vietnam etc) to be what they are. You don't need to defend Un or Xi or any other "boogieman". Criticize these nations if you think it'll help them not dismiss you as simply spouting propaganda. No nation is perfect. Even Sankara made mistakes. As long as you can help them disassociate the West and capitalism from freedom and democracy.
And in this you're not alone. The material conditions themselves are on your side. Crises that are capable of radicalizing people happen all the time. Just look at how much the world has undergone in the past year. Covid, George Floyd, the latest election fiasco - they have all pushed my boomer mom further to the left. This isn't because 2020 was particularly ripe for radicalization, but because for the first time she knew that there was something to the left that was more progressive and more democratic. And she knew she had to move to the left because she'd seen the failings and the evils of liberalism, of the Democrats, of the moderates.