The light emitted from light, light_spot, and light_environment is completely static in that it won't cast real-time shadows what-so-ever. light_dynamic can be moved but, if I remember correctly, it can't cast shadows and even if it could I doubt it would use actual projection to make the shadows bigger if the object is closer.
The best way to make a dynamic shadow is to use render-to-texture shadows, which can be controlled through the shadow_control entity. However, these are not porjected through the 3D skybox, so you must place a scaled up version of the original object in the actual world for it to cast shadows, and you must increase the shadow distance in the shadow_control entity if it's more than 75 units above the ground, which it probably is in your case. You can't use a func_brush in the world, since they don't cast RTT shadows. However, I believe that func_physbox entities cast shadows, but those can be tricky to work with.