I've always been interested in history but often fell into the trap of thinking I understood how things happened because I knew a couple of facts about an event that most people hadn't heard of. I've been trying to approach the topic more seriously.
Right now I'm reading "Battle Cry of Freedom" to learn something from a different perspective than my Lost Cause supporting high school history teacher. Other books I have read recently are Robert Caro's "The Path to Power", Edmund Morris's "The Rise of Theodore Roosevelt", Ibram X. Kendi's "Stamped from the Beginning", David Halberstam's "The Fifties", Joseph Ellis's "Founding Brothers", Arthur Herman's "Gandhi and Churchill", Stephen Ambrose's "Nothing Like it in the World".
I feel like I have at least some historical perspective up until the end of the 1950s. After the 1950s I feel my knowledge is all through cultural osmosis rather than actually reading anything that tries to grapple with events from a more rigorous perspective.
Under the guidance of the 20-year-rule, what would be a good modern history to start with. I'm curious what the community might consider to be the best preamble to the present. The rise of conservatism and Reagan? The Clinton years? The fall of the Soviet Union? The creation of the internet? Thoughts?
Specifically around the fall of the Soviet Union:
It's on the book list (I thought we updated the Russia section), but an old go-to is David Remnick's Lenin's Tomb. It's well written and engaging, but I'd also point out that it's a collection of journalistic dispatches he wrote while posted to Moscow (so in this sense it's a bit similar to William Shirer's Rise and Fall of the Third Reich): it's great for first-hand impressions, less so for actually putting all the pieces together with a sense of historic perspective.
There still isn't a lot of "proper" history written on that period, but two books that I personally recommend that are engaging and written by (in my opinion) pretty good academic historians are Armageddon Averted by Stephen Kotkin and The Last Empire by Serhii Plokhy. The former looks at the fall of the USSR in the perspective of long-term trends (and so it covers the period 1970 to 2000). The latter is more of a microhistory, focusing specifically on the events of August to December 1991 that led to the dissolution.
If we're talking about books about the end of the Cold War (which isn't actually the same as the dissolution of the USSR), then a good book to start with would be the aptly-named End of the Cold War, 1985-1991 by Robert Service. This is mostly a diplomatic history and Service devotes a fair deal of space to background on both Reagan and his administration and Gorbachev and his team. Victor Sebestyen's Revolution 1989: The Fall of the Soviet Empire is a well-regarded history of the 1989 revolutions in Eastern Europe that marked the end of the Cold War proper.
Regarding the history of the Internet, others should chime in but personally John Cassidy's Dot.Con was a great read that helped provide a lot of the backstory to what I personally remember about the tech bubble.
If you wanted books about the fall of the USSR and the creation of the Internet, there is actually a subgenre of that! Andrei Soldatov and Irina Borogan's The Red Web: The Struggle Between Russia's Digital Dictators and the New Online Revolutionaries is a great example of this, as well as Benjamin Peters' How Not to Network a Nation: The Uneasy History of the Soviet Internet.
It’s hard to beat Twitter superstar and Princeton historian Kevin Kruse’s (with Julian Zelizer) “Fault Lines: A History of the United States Since 1974” which is a history of post-Watergate America. It particularly examines the way cultural conflicts manifested themselves in the politics of the 80s and 90s.
Have a look at the subreddit book list. The link is to the North America section, but there are entries for other parts of the world too.
/u/jdbyer and /u/indyobserver and /u/Kochevnik81 are flaired for some of the topics you've mentioned, and I cannot post an intra-subreddit link without pings.
The rise of Reagan is largely concomitant with the fall of the New Deal.
When I teach this, I usually use these books. I think they do a nice job of showing how post-war America shifted to a politics of self-interest, leaving mass unionization and a mild collectivism behind.
Gerstle, ed., The Rise and Fall of the New Deal Order Dated, yes, but still useful.
Jackson, Crabgrass Frontier on suburbanization and white flight.
McGirr, Suburban Warriors excellent work on how small groups of conservatives worked to get their messages out and candidates elected.
Jacobs, Pocketbook Politics focuses on a politics of self. "Are you better off now than you were 4 years ago?" Stuff.