What would make a car sound like a big rig stoping?

If you are meaning a loud howling or moaning sound, probably so, assuming the brakes work right. You can use some 220 sandpaper (I like the drywall sanding grids) to rough up the drum surface if the surface is not too scored up, and see if that does it. Check everything else while you are in there too.

X2
Probably just a surface mismatch.