diff --git a/Makefile b/Makefile
index 8599190c..ee053d2c 100644
--- a/Makefile
+++ b/Makefile
@@ -97,6 +97,32 @@ ifeq ($(WINDOWS_BUILD),1)
   endif
 endif
 
+# macOS overrides
+ifeq ($(HOST_OS),Darwin)
+  OSX_BUILD := 1
+  # Using MacPorts?
+  ifeq ($(shell test -d /opt/local/lib && echo y),y)
+    OSX_GCC_VER = $(shell find /opt/local/bin/gcc* | grep -oE '[[:digit:]]+' | sort -n | uniq | tail -1)
+    CC := gcc-mp-$(OSX_GCC_VER)
+    CXX := g++-mp-$(OSX_GCC_VER)
+    CPP := cpp-mp-$(OSX_GCC_VER) -P
+    PLATFORM_CFLAGS := -I /opt/local/include
+    PLATFORM_LDFLAGS := -L /opt/local/lib
+  else
+    # Using Homebrew?
+    ifeq ($(shell which brew >/dev/null 2>&1 && echo y),y)
+      OSX_GCC_VER = $(shell find `brew --prefix`/bin/gcc* | grep -oE '[[:digit:]]+' | sort -n | uniq | tail -1)
+      CC := gcc-$(OSX_GCC_VER)
+      CXX := g++-$(OSX_GCC_VER)
+      CPP := cpp-$(OSX_GCC_VER) -P
+      PLATFORM_CFLAGS := -I /usr/local/include
+      PLATFORM_LDFLAGS := -L /usr/local/lib
+    else
+      $(error No suitable macOS toolchain found, have you installed Homebrew?)
+    endif
+  endif
+endif
+
 ifneq ($(TARGET_BITS),0)
   BITS := -m$(TARGET_BITS)
 endif
@@ -164,6 +190,7 @@ endif
 # in the makefile that we want should cover assets.)
 
 ifneq ($(MAKECMDGOALS),clean)
+ifneq ($(MAKECMDGOALS),cleantools)
 ifneq ($(MAKECMDGOALS),distclean)
 
 # Make sure assets exist
@@ -176,11 +203,12 @@ endif
 endif
 
 # Make tools if out of date
-DUMMY != make -C tools >&2 || echo FAIL
+DUMMY != CC=$(CC) CXX=$(CXX) $(MAKE) -C tools >&2 || echo FAIL
 ifeq ($(DUMMY),FAIL)
   $(error Failed to build tools)
 endif
 
+endif
 endif
 endif
 
@@ -352,7 +380,7 @@ DEP_FILES := $(O_FILES:.o=.d) $(ULTRA_O_FILES:.o=.d) $(GODDARD_O_FILES:.o=.d) $(
 SEG_FILES := $(SEGMENT_ELF_FILES) $(ACTOR_ELF_FILES) $(LEVEL_ELF_FILES)
 
 ##################### Compiler Options #######################
-INCLUDE_CFLAGS := -I include -I $(BUILD_DIR) -I $(BUILD_DIR)/include -I src -I .
+INCLUDE_CFLAGS := $(PLATFORM_CFLAGS) -I include -I $(BUILD_DIR) -I $(BUILD_DIR)/include -I src -I .
 ENDIAN_BITWIDTH := $(BUILD_DIR)/endian-and-bitwidth
 
 # Huge deleted N64 section was here
@@ -390,7 +418,6 @@ ifeq ($(WINDOWS_BUILD),1) # fixes compilation in MXE on Linux and WSL
   OBJCOPY := objcopy
   OBJDUMP := $(CROSS)objdump
 else ifeq ($(OSX_BUILD),1)
-  CPP := cpp-9 -P
   OBJDUMP := i686-w64-mingw32-objdump
   OBJCOPY := i686-w64-mingw32-objcopy
 else # Linux & other builds
@@ -541,7 +568,7 @@ else ifeq ($(TARGET_RPI),1)
   LDFLAGS := $(OPT_FLAGS) -lm $(BACKEND_LDFLAGS) -no-pie
 
 else ifeq ($(OSX_BUILD),1)
-  LDFLAGS := -lm $(BACKEND_LDFLAGS) -no-pie -lpthread
+  LDFLAGS := -lm $(PLATFORM_LDFLAGS) $(BACKEND_LDFLAGS) -lpthread
 
 else
   LDFLAGS := $(BITS) -march=$(TARGET_ARCH) -lm $(BACKEND_LDFLAGS) -no-pie -lpthread
@@ -571,13 +598,6 @@ ZEROTERM = $(PYTHON) $(TOOLS_DIR)/zeroterm.py
 
 all: $(EXE)
 
-# thank you apple very cool
-ifeq ($(HOST_OS),Darwin)
-  CP := gcp
-else
-  CP := cp
-endif
-
 BASEPACK_PATH := $(BUILD_DIR)/$(BASEDIR)/
 BASEPACK_LST := $(BUILD_DIR)/basepack.lst
 
@@ -590,7 +610,7 @@ res: $(BASEPACK_PATH)
 # prepares the basepack.lst
 $(BASEPACK_LST): $(EXE)
 	@mkdir -p $(BUILD_DIR)/$(BASEDIR)
-	@echo -n > $(BASEPACK_LST)
+	@touch $(BASEPACK_LST)
 	@echo "$(BUILD_DIR)/sound/bank_sets sound/bank_sets" >> $(BASEPACK_LST)
 	@echo "$(BUILD_DIR)/sound/sequences.bin sound/sequences.bin" >> $(BASEPACK_LST)
 	@echo "$(BUILD_DIR)/sound/sound_data.ctl sound/sound_data.ctl" >> $(BASEPACK_LST)
diff --git a/tools/Makefile b/tools/Makefile
index b6b7babf..efc9cba8 100644
--- a/tools/Makefile
+++ b/tools/Makefile
@@ -1,5 +1,5 @@
-CC := gcc
-CXX := g++
+CC ?= gcc
+CXX ?= g++
 CFLAGS := -I../include -I. -Wall -Wextra -Wno-unused-parameter -pedantic -std=c99 -O2 -s
 LDFLAGS := -lm
 PROGRAMS := n64graphics aifc_decode aiff_extract_codebook mio0 vadpcm_enc tabledesign skyconv
@@ -31,7 +31,7 @@ vadpcm_enc_CFLAGS := -Wno-unused-result -Wno-uninitialized -Wno-sign-compare -Wn
 LIBAUDIOFILE := audiofile/libaudiofile.a
 
 $(LIBAUDIOFILE):
-	@$(MAKE) -C audiofile
+	@CC=$(CC) CXX=$(CXX) $(MAKE) -C audiofile
 
 all: $(LIBAUDIOFILE) $(PROGRAMS) $(CXX_PROGRAMS)
 
@@ -46,4 +46,4 @@ endef
 
 $(foreach p,$(PROGRAMS),$(eval $(call COMPILE,$(p))))
 
-.PHONY: all clean default
\ No newline at end of file
+.PHONY: all clean default
diff --git a/tools/audiofile/Makefile b/tools/audiofile/Makefile
index 5f3f3e1d..f1c36d79 100644
--- a/tools/audiofile/Makefile
+++ b/tools/audiofile/Makefile
@@ -1,4 +1,4 @@
-CXX := g++
+CXX ?= g++
 
 libaudiofile.a: audiofile.o
 	ar rcs libaudiofile.a audiofile.o