Bitch I’m Madonna

she obviously loves the song, not only covering it way back when but revisiting it with a video for Something To Remember and now on Rebel Heart which are three distinctively different eras in her career. its not her strongest tune, i have a soft spot for the Soulpower Remix its sooo 90s

The fact that it wasn't released as a single is because she didn't want to be a covers singer for a long time. In the 80s, such covers were regarded as "bonus" or b-side material, not original enough (indeed) for a young artist. In the 90s, times had changed and covers were trendy again, hence Fever, the remix single version of LDLHA and American Pie.

Well, then it most definitely should have been the b-side to Over and Over which deserved a single release over Gambler (which should have been the b-side to Crazy for You).