(((Rain))))) how old is he now? sorry to have to ask
Does he have a ear infection maybe. both of my kids had alot of those , it always affected thier sleep. Does he have colic? My son had that till age one.
I always found a warm bath and quietness helped him alot. Also rocking him after the bath always helped.
The letting them cry it out i could never do.
The other thing that helped with my son as he had sleep issues because of the colic was a bubble machine I called it. It was a jar with a air pump thing in it that made a soothing sound. Believe or not it worked

To this day I have fish tanks that are near his room. Because he is use to the noise.
My daughter I had a tape of soft music she use to listen too

hope this helps .
Muffy