Microsoft actually sort of did that with Windows 9x. There was a lot of Windows 3.1 and DOS software and drivers that they wanted to remain compatible, and tho

Microsoft actually sort of did that with Windows 9x. There was a lot of Windows 3.1 and DOS software and drivers that they wanted to remain compatible, and those relied on DOS quirks. So, they had a copy (copies) of DOS always resident in RAM, mostly unused. All DOS syscalls (interrupts) were hooked so that they would call Windows instead. If a program added its own hooks, Windows would detect that and switch to 16-bit mode for the relevant operation. When the custom hook completed, it would call the next hook in the chain, which was the one that went back to Windows. Of course, this relied on Windows understanding DOS's internal data structures and keeping them in sync with what Windows was doing. A similar technique was used for drivers, if Windows found a driver it didn't understand, it would let that driver run in 16-bit mode. Raymond Chen (of Microsoft fame) explains this much better than I ever could https://devblogs.microsoft.com/oldnewthing/20071224-00/?p=24063 https://devblogs.microsoft.com/oldnewthing/20071224-00/?p=24...