My 15 year old son say that he has headaches a lot and that he can't sleep. At this point do I see a Dr. or has someone else had this problem

Headaches in teen boys

You definitely need to have your son looked at by a physician. If his headaches are so severe there could be a problem that could be quite severe such as a head tumor, migraines, etc. Sometimes the doctor will do a MRI or Cat scan to rule out a tumor. If he is prescribed medicine for the headaches and they don't get better but get worse, then the MRI, etc. will probably be ordered to further diagnose the headaches.