If you build it, they will come … maybe
Throughout the console's depressingly brief two-year lifecycle, Microsoft and Sega's plan never reached the heights of its potential.
Exact figures of the amount of Windows CE-based Dreamcast games released aren't publicly available, but some estimations range from about 50 to 60. Whether this quantity measured up to the expectations of the two companies is irrelevant at this point.
Quality is the metric that matters most. And that was the biggest problem with most of the Dreamcast games built on Windows CE. They weren't very good.
There were a few gems to come out of the collaboration, like Hidden & Dangerous, Sega Rally 2 and Resident Evil 2. However, noticeably missing from the list are any of the games that helped put the Dreamcast on the map. Sonic Adventure, Shenmue, Jet Grind Radio and many more (Seaman, anyone?) were built using Sega's proprietary interface instead.
Microsoft put the tools in the hands of the developers, but it didn't pan out. Maybe offering two programming interfaces for developers to choose from was one too many. It's also possible that the cross-compatibility dream that Microsoft and Sega shared was too ahead of its time.
Regardless of the real reason for the failed partnership, it was a learning opportunity for Microsoft. The company might have only gained a little insight as to what worked and what didn't in the game console market, but it was enough to get started on its own box.
Unfortunately, that's where the hardware side of the story ends for Sega. The Dreamcast would be its last go. But Kotaku reported on one last attempt from Sega to keep the Dreamcast's saga alive.
Isao Okawa, who was Sega's chairman at the time, visited Bill Gates numerous times to negotiate the possibility of making Dreamcast games compatible on Microsoft's new Xbox console, which was in development at the time. Unfortunately, the talks fell through. Sega did, however, go on to bring several of its hit Dreamcast franchises, such as Shenmue, Crazy Taxi and Jet Grind Radio to the Xbox.
The future of Windows on Xbox
Since the release of the original Xbox, Microsoft has been rather quiet about the tools it provides to developers who want to make games. It's a stark contrast from how much it boasted about its Windows CE tools on the Sega Dreamcast.
However, if you fast-forward to current day, Microsoft announced – no, it practically shouted from the rooftops – that Windows 10 is coming to Xbox One this autumn. Thinking back on its experience with the Dreamcast, the familiar sense of enthusiasm coming from Microsoft is palpable.
The return of Windows on a home console at least owes its thanks to the Sega Dreamcast. How a similar plan will pan out on the Xbox One is anyone's guess at this point. But, the gaming world (perhaps Sega, too) will be watching very closely as it happens this November.