There is a gcc for 8088: https://github.com/tkchia/gcc-ia16
It is used to build a whole 16 bit Linux called ELKS: https://github.com/ghaerr/elks Parts of ELKS such as its libc can be built with Open Watcom as well.
There is also a recent version of dev86: https://codeberg.org/jbruchon/dev86