I can give you the names of a handful of books that might be useful. Some are more technical, some less so. Some are more about personalities, some about the business aspects of things, some more about the actual technology. I don't really have time to try and categorize them all, so here's a big dump of the ones I have and/or am familiar with that seem at least somewhat related.

The Mythical Man-Month: Essays on Software Engineering - https://www.amazon.com/Mythical-Man-Month-Software-Engineeri...

Hackers: Heroes of the Computer Revolution - https://www.amazon.com/Hackers-Computer-Revolution-Steven-Le...

The Cuckoo's Egg: Tracking a Spy Through the Maze of Computer Espionage - https://www.amazon.com/Cuckoos-Egg-Tracking-Computer-Espiona...

Where Wizards Stay Up Late: The Origins of the Internet - https://www.amazon.com/Where-Wizards-Stay-Up-Late/dp/0684832...

Open: How Compaq Ended IBM's PC Domination and Helped Invent Modern Computing - https://www.amazon.com/Open-Compaq-Domination-Helped-Computi...

Decline and Fall of the American Programmer - https://www.amazon.com/Decline-American-Programmer-Yourdon-1...

Rise and Resurrection of the American Programmer - https://www.amazon.com/dp/013121831X/ref=sr_1_1?dchild=1&key...

Accidental Empires: How the Boys of Silicon Valley Make Their Millions, Battle Foreign Competition, and Still Can't Get a Date - https://www.amazon.com/Robert-X-Cringely/dp/0887308554/ref=s...

Softwar: An Intimate Portrait of Larry Ellison and Oracle - https://www.amazon.com/Softwar-Intimate-Portrait-Ellison-Ora...

Winners, Losers & Microsoft - https://www.amazon.com/Winners-Losers-Microsoft-Competition-...

Microsoft Secrets - https://www.amazon.com/Microsoft-Secrets-audiobook/dp/B019G2...

The Friendly Orange Glow: The Untold Story of the PLATO System and the Dawn of Cyberculture - https://www.amazon.com/The-Friendly-Orange-Glow-audiobook/dp...

Troublemakers: Silicon Valley's Coming of Age - https://www.amazon.com/Troublemakers-Silicon-Valleys-Coming-...

Hard Drive: Bill Gates and the Making of the Microsoft Empire - https://www.amazon.com/Hard-Drive-Making-Microsoft-Empire/dp...

Masters of Doom: How Two Guys Created an Empire and Transformed Pop Culture - https://www.amazon.com/Masters-Doom-Created-Transformed-Cult...

The Supermen: The Story of Seymour Cray and The Technical Wizards Behind the Supercomputer - https://www.amazon.com/Supermen-Seymour-Technical-Wizards-Su...

Bitwise: A Life in Code - https://www.amazon.com/Bitwise-Life-Code-David-Auerbach/dp/1...

Gates - https://www.amazon.com/Gates-Microsofts-Reinvented-Industry-...

We Are The Nerds - https://www.amazon.com/We-Are-Nerds-audiobook/dp/B07H5Q5JGS/...

A People's History of Computing In The United States - https://www.amazon.com/Peoples-History-Computing-United-Stat...

Fire In The Valley: The Birth and Death of the Personal Computer - https://www.amazon.com/Fire-in-Valley-audiobook/dp/B071YYZJG...

How The Internet Happened: From Netscape to the iPhone - https://www.amazon.com/How-Internet-Happened-Netscape-iPhone...

Steve Jobs - https://www.amazon.com/Steve-Jobs-Walter-Isaacson/dp/1451648...

The Idea Factory: Bell Labs and the Great Age of American Innovation - https://www.amazon.com/Idea-Factory-Great-American-Innovatio...

Coders - https://www.amazon.com/Coders-Making-Tribe-Remaking-World/dp...

Dreaming in Code: Two Dozen Programmers, Three Years, 4,732 Bugs, and One Quest for Transcendent Software - https://www.amazon.com/Dreaming-in-Code-Scott-Rosenberg-audi...

The Pentagon's Brain: An Uncensored History of DARPA, America's Top-Secret Military Research Agency - https://www.amazon.com/Pentagons-Brain-Uncensored-Americas-T...

The Imagineers of War: The Untold Story of DARPA, the Pentagon Agency That Changed the World - https://www.amazon.com/Imagineers-War-Untold-Pentagon-Change...

The Technical and Social History of Software Engineering - https://www.amazon.com/Technical-Social-History-Software-Eng...

Also...

"The Mother of All Demos" by Doug Englebart - https://youtu.be/yJDv-zdhzMY

"Jobs vs Gates" - https://www.amazon.com/Jobs-Vs-Gates-Hippie-Nerd/dp/B077KB96...

"Welcome to Macintosh" - https://www.amazon.com/Welcome-Macintosh-Guy-Kawasaki/dp/B00...

"Pirates of Silicon Valley" - https://www.amazon.com/Pirates-Silicon-Valley-Noah-Wyle/dp/B...

"Jobs" - https://www.amazon.com/Jobs-Ashton-Kutcher/dp/B00GME2NCG/ref...

And while not a documentary, or meant to be totally historically accurate, the TV show "Halt and Catch Fire" captures a lot of the feel of the early days of the PC era, through to the advent of the Internet era.

https://www.amazon.com/I-O/dp/B00KCXJCEK/ref=sr_1_1?crid=U6Z...

And there's a ton of Macintosh history stuff captured at:

https://www.folklore.org/

The book Softwars spends a lot of time on this topic, where Larry Ellison blasted all of his integration partners for over-customizing their solutions when the correct approach was to update the business processes to match the software:

https://www.amazon.com/Softwar-Intimate-Portrait-Ellison-Ora...

* Angel by Jason Calacanis about angel investing. (http://amzn.to/2eOqkyn)

* Tools of Titans by Tim Ferris (http://amzn.to/2uYv9LH)

* Softwar about Larry Ellison (http://amzn.to/2uYHHmf)

* Wild ride about Uber (http://amzn.to/2eOqrdh)

* Social Intelligence: the new science of human relationships (http://amzn.to/2uYGueV)

* Rereading - Letters to shareholders by Warren Buffett (http://amzn.to/2h3xFe0)

Not really sure what to say about this. I don't know Ellison, nor do I own Oracle stock, or have any particular interest in Oracle per-se. But nonetheless, I've always seen Ellison as an important character in our industry, and after reading a biography about him, I felt a sort of kinship with him based on some shared interests.

At any rate, it definitely feels like the "end of an era" in a sense. I got my start in this industry in the mid to late 90's when Oracle, IBM, Novell, Microsoft, Borland, etc. were duking it out for supremacy, and - for better or worse - you've never really been able to escape Oracle's shadow to some extent. And Ellison was Oracle, in so many ways.

Edit: It's been a while, but I think this[1] was the biography I read. I'll just say this: regardless of what you think of Ellison, he's an interesting character and reading about the history of Ellison / Oracle is quite fascinating.

[1]: http://www.amazon.com/Softwar-Intimate-Portrait-Ellison-Orac...

Yeah, I was being hyperbolic to try to make the point -- you can dismiss anything as merely a frigging X. You're absolutely right with regard to Oracle.

(Tangent: for anyone interested in Oracle's history/business, or just enterprise software in general, I highly recommend http://www.amazon.com/dp/0743225058)