6. The Original Xbox Almost Had Dreamcast Compatibility
The Sega Dreamcast was like an open bar for adults at a child's birthday party: Awesome, but doomed to end poorly. And like a drunk man being pulled out of an inflatable bouncy castle, Sega Chairman Isao Okawa wasn't going to go without a fight.
Things were already looking bleak for the Dreamcast by the early 2000s, and Okawa was looking for a way to extend the platform's lifespan. At the same time, Microsoft was developing a new console called the Xbox, and Okawa saw that as an opportunity to prolong the Dreamcast's legacy.
He approached Microsoft with an intriguing idea: Make the Xbox compatible with Dreamcast games. And he didn't just pitch this idea to some no-name project manager, he went straight to the top - Bill Gates himself.
Gates was reportedly on board with the idea, and it would've been a win-win for both sides - Sega would have extended their dying platform while giving the Xbox a huge, well-regarded library at launch. But there was one problem: Microsoft would not guarantee online support for Dreamcast games, which Okawa considered non-negotiable. Neither side would budge on the issue, and the two companies were unable to come to an agreement.