Hmm...very difficult request, not many watch old style movies, I'm going to list some gangland movies/series that could potentially fit, maybe you find something:
New World, almost no ladies, but fits the cool criteria i think
For the Emperor, it's a noir, so sexy lady check, action also check, not sure about chipmunks
Last, a broker on the run hides between homeless folks who operate like gang, lots of action, chipmunks and maybe sexy ladies
Now into hardboiled melodrama category:
Giant
Sandglass
To a lesser degree perhaps:
Swallow the Sun
Friend, Our Legend
Cruel City
