Usually, you cannot specify rules with commands multiple times.
foo.o: foo.c $(CC) $< -o $@ foo.o: foo.c $(CC) $< -o $@ -g # Error!
But you can do it if you use double-colon rules:
foo.o:: foo.c $(CC) $< -o $@ foo.o:: foo.c $(CC) $< -o $@ -g # OK. make will run GCC twice to build foo.o
Not sure how this feature could be useful...