The Rise of Microsoft Windows Part 2: Windows 2x

After many delays and becoming the butt of many industry jokes, Windows 1 had finally staggered onto the market at the end of 1985. It was met by basically complete indifference, as it performed poorly on most people's computers, and lacked any sort of compelling software to kickstart adoption and thereby drive more interest from software developers and users alike.

But Microsoft pressed on with the followup, Windows 2. Although most of Microsoft's time and attention was focused on their partnership with IBM to develop a shiny new operating system, OS/2, and in spite of the fact that Steve Ballmer and others inside of Microsoft saw no point in continuing to develop the successor to the original Windows release, Bill Gates refused to call a halt to its development.

Windows 2's story is a complex one, and IBM, OS/2, and OS/2's GUI Presentation Manager weave in and out of it at various points, together with Apple, HP, Compaq, and others.

It's development was also further complicated by the decision to break it into two pieces, one for 8088/8086 machines and one solely aimed at systems utilizing the powerful new 386 processor.

Battling a wide variety of obstacles, Windows 2.0 eventually succeeded in making it to market, and it and its successor Windows 2.1 eventually proved that Windows could be a viable product that could take Microsoft into the 1990s, and allow them to break free of riding the IBM tiger.

In many ways, Microsoft's incredible growth in the 1990s was rooted in the success that Windows 2x delivered. This sprawling, messy, confusing, contradictory, poorly documented and incredibly fascinating story is the focus of this video. I hope you enjoy it :)

0:00:00 - Windows 1 Post-Launch
0:07:29 - Windows 2.0 first hint
0:11:25 - Microsoft and IBM
0:24:56 - Seattle Computer Products
0:31:30 - IBM's New OS
0:33:43 - DSR and TopView
0:35:16 - Windows and SAA
0:39:53 - Winthorne
0:44:23 - Windows 2.0's development
0:54:35 - EMS 4.0
0:57:18 - Splitting Windows 2 into two versions
1:03:05 - Windows and Presentation Manager
1:11:08 - Windows/386 and Windows 2.0 shown off
1:12:47 - Windows 2.0's murky release timeline
1:21:16 - Windows 2.0 reception and use
1:29:42 - Windows/386 on The Computer Chronicles
1:37:32 - Windows 2.1
1:50:27 - HP NewWave
1:51:53 - Apple versus Microsoft
1:56:38 - Wrapup

[AnotherBoringTopic]

Extended thoughts Substack post


Topics covered:
Did Microsoft copy the Macintosh with Windows 2x?
IBM and the 386
Windows 2x bundle deals with OEM’s
When did Compaq start working with Microsoft on Windows/386?
Windows/386 Preemptive Multitasking
Who All Worked on Windows 2x?
Why was the 286 considered crippled?

[Klatchan]

My dude not only do you have a PRIMARY source, you're correcting some of the secondary sources. You put so much work into this. Thank you.

[jourdanfarmer]

I’m going to be honest, I thought this part 2 was never going to come out. I should have never doubted you. This is awesome

[Birdman_in_CLE]

I know these are a chore to put together, but it is worth it. You put together the best tech documentaries period. Your research, and production are appreciated beyond what I can express here. Thank you for your work!

[juliouribe]

Oh man I've been waiting ages for this

[Trenchbroom]

As someone who has been reading Infoworld for fun over the past few years (i'm at July 1988 right now) and who has seen each episode of The Computer Chronicles multiple times, I was happy to come across this well-written and edited video. I will make one comment about the "shrink wrapped Windows/386" situation: I worked in a video store through college for five years in the mid-90s, spending my days unwrapping new tapes, shrink wrapping the covers with a cardboard stuffer put inside so that the cover could be put on the shelf for display, and re-shrink wrapping used tapes to be put out for sale. Because of this, I don't trust the validity of shrink wrapped items being new/unused at all (especially ones where you can see the melt line along the edges of the item, as you see in the photo). In this case I think it is best to stick with the contemporary date of Jan. 1988 as the real release date. I'm now looking forward to going back and watching your OS/2 and PC clone videos. Keep up the good work!

[mikehibbett]

Great coverage. As a graduate in 1986, working in PC graphics device driver development, I lived through these developments. Without knowing the back story!

[beJT]

I remember my friend's dad being a 'windows programmer' back in the late 80s. He saw it as a huge opportunity and used to tell us about it every chance he could.

[andrehinds]

In 1991 I taught an Intro to Desktop Publishing class at the University of Maryland. The classroom was in an auditorium-sized room with 35 low-end PS/2 machines running Windows 2x and PageMaker. I was an expert on PageMaker for the Mac and found that PageMaker for Windows was from the Stone Age. The OS couldn’t handle the wide variety of fonts the Mac could. The only variance for fonts on PM for Winows 2x were single generic versions for serif and sans-serif fonts. You had to print out the page in order to see how things worked out. I doubt if there were any serious commercial publishers using PM on Windows 2x.

[geraldmollineau]

Unbelievable to amount of research you did for this and your ability to present the information in a coherent interesting manner. This is awesome. Clearly a labour of love.

[jtridexter]

An absolute pleasure—no distracting background music and a flawless presentation.

[KW-eipi]

Excellent presentation. And, unlike so many YouTube presenters, you are an excellent speaker. A pleasure to listen to. Thank you.

[boomerdB]

Excellent video and a big THANK YOU. I remember being told "a year in the computer field is like dog years, aka 7 years anywhere else." My career rode the wave of developments of Win 3.1/3.11 (networking), Win 9x (Internet), Win XP/7/8/10/11 (IT security). Keep up the great work!!

[konstantinoskinnas]

I think this is the best channel for computer (science) history. Keep up the good work!

[prispalos]

This is a proper documentary. Wow. This was worth the wait. Please do not be discouraged by the views! This is amazing!

[herberttlbd]

HMA gave you 64K - 16 bytes of extra memory. The 8086/8088 architecture used 16 bit segment registers, shifted by 4 bits, added to 16 bit pointers to give 20 bit addresses allowing 1M access. The trick was that segment FFFF with any pointer above 000F would wrap-around to on systems that had 20 address lines, like the 86/88, but would continue on to for those that had 21+ address lines, like the 286+ processors. There was one caveat though in that IBM was aware that this issue could cause bugs for 86/88 code that relied on the wrap-around and added circuitry that could enable/disable this called the A20 gate. HIMEM.SYS was the driver you loaded in DOS to disable the wrap-around.

[tarstarkusz]

1:59:32 GEOS is the most underrated PC gui of all time. It was everything Windows should have been. It was MUCH, MUCH faster and used less RAM. One of the most common applications of the early-mid 90s used the geos runtime, AOL for DOS. My cousin actually a bought a PC in 1993 or 94 that came with GEOS as the main windows like OS.

[Sashko_Dee]

If part one was 30 minutes and part two was 2 hours, then if current trends continue then part three should be *EIGHT HOURS LONG!!!* And I would watch every minute of it.

[zexelon]

Oh for the love of all that is good and right... please not another year before the next installment! Just came across this documentary and need more!😆 Very well done!

[retroasobi]

I just finished reading the "Barbarians Led by Bill Gates" as cited in many parts of the video, and with corrected informations through it. A very complete and detailed video. Hats off to you, sir