I did a little reading to reaffirm what I recalled from some behavior books. The Character of Cats, by Stephen Budiansky (and some others I've read) state that if a cat is getting people up in the middle of the night, try having a play and exersize session right before bedtime. As for the five AM activity, he also indicates that cats in the wild tend to be "crepuscular" animals, most active at dawn and dusk, but that they do adapt to our schedules. Ours sometimes arise at that hour and frisk around, but go back to sleep until we wake.

Thank you all for the replies.

I do play with him before bed- laser pointer, feather toy, etc.
But as soon as I go to sleep he starts meowing again. Many a night I have sat on my bed at 3am with a feather toy, swinging it around!

He doesn't get as tired out by the toys as when he was a kitten. I assume this is natural with age, although he is only 4. (if that isn't normal, please let me know!)

I can't help but wonder if he was meant to be an outdoor cat.

I totally agree that he needs to learn to not be carrying on at all hours. If it's possible to put him in another room that might help  (you might need earplugs, though). He is learning that he can get you to play with him to quiet him down. I would not put him outdoors. Outdoor cats live in a very dangerous world and you might well end up with disease, injury or even death. Better to spend some time training him now ~ maybe not fun in the short run, but better in the long run.

My boy, Jess, tends to attack one of my other cats during the night (usually the 4 - 6 am times) and I suspect that he sees other cats outside and that upsets him. This week I have started shutting him in his own room for the night. I feel bad to have to do that, but I will not have him attacking the others so we have some playtime, then when I go to bed, he gets a bit of wet food "treat" iin his room and that's it. He has done a bit of crying, but it's less each night. I wish he could be out with the others, but he can't. I'm guessing he will be so used to this within a few days that it will just be part of our routine.

You're not being mean, but as catbird said, you're teaching him.
Good luck!
catmom5

There was one time 2 yrs ago when my male DSH (neutered) did the howling thang to excess... we only just moved to a new place and so I knew it was part stress, part excitement, part whatever... nothing worked to shut him up... I "sin-binned" him in his carrier and stowed it away in the laundry room... I squirt him with water... I sprayed essence into the air... shook a pill bottle real loud to stratle him out of the howling... he only cried harder... and then! I discovered Rescue Remedy... whenever he showed signs that he was about go a-howling and a-meowing, I rubbed a drop of Rescue Remedy on each of his ears.  He'd meow-meow a bit and then inevitable settle down to relax.  I don't now if this will work on your kitty, Micky, but perhaps you could give one of those anti-stress calming products to your cat.  Rescue Remedy is just one of these products... Feliway is another (plug-in, which will probably work very well for you)... there are homeopathic drops you can put in the cats' drinking water...

Mickey, if it makes you feel any better, Fizzy wakes us up howling almost every night, too.  Usually she's announcing that she has brought us a midnight snack (stuffed mouse), but sometimes she's just "talking" to us.  I used to call to her to try to quiet her, but then realized that I was probably reinforcing her actions.  We've started closing the door at night but she sits outside hoping.....and howling.  But usually not for more than a few minutes at a time. She has done this for as long as we've had her.  It is a bit frustrating.  I think the Rescue Remedy or something similar is worth a try.  On the other hand, Scooby never crys or meows, just claws on the carpet outside the door   We can't win!

The idea of Rescue Remedy is interesting - Stan has been yowling from about 5:00 AM every morning for a couple weeks now. Butter doesn't react - he just sleeps away...

We've installed a Feliway diffuser, and it's been up and running for over a month now. Stan was quite distant, but now is really demanding of affection and attention. I wonder if it's related to the diffuser...

Mickey - Does the cat yowl when you open the door?

I have recently read - and believe it - that closing a door makes them crazy, especially if they're indoor cats. With limited territory, they get resentful when they lose access to any of it.