We have a six year old neutered boy who's strictly an indoor cat, and is a bit chunky but not super obese. If you free-feed him he will gulp his food down like he's starving then puke it back up, like clockwork.

So, we've been feeding him smaller portions more times per day. Problem is that he's always acting like he's starving, and  sits out of sight, waiting, and when he sees us he screams and runs to his dish, wanting more food.

Sounds like he's a food addict, will time cure him of this eventually?

Smaller more frequent meals like you said
Do not make eye contact

That's just how some cats are.  We have two of our 5 that do it.  One will eat so much she will vomit it all up.  She's very lean because of that.  The other will devour as much food as possible as often as possible and was getting pretty fat.

Another of our cats has some health issues and has to eat special food so we had to go from feeders to feeding them 3 times a day.  It controls their intake and they get plenty of food. The two overeater cats are always trying to score a meal whether it's their food or ours.  

I would highly recommend a cat food "robot" like the feeder-bot that Litter Robot sells.  There are several different kinds that are programmable that will feed your kitty a specific amount at specific times.  This allows you to control his portions and when he eats.  It also disassociates you from his food.  So he doesn't see you as his food source provider as much.  Hopefully that will make him less likely to constantly beg you to feed him.  I'd recommend filling the feeder without him seeing you do it as well.  

What are you feeding him?  Maybe there's room for improvement of the diet, stick to ribs type food, or with different nutrients.

Smaller meals more frequent are a good way to go. That's what my cat gets, but she's not food motivated and I have to basically chase her around the desk with a bowl to get her to eat the good stuff.

It might never go away. Clarence is coming up on 15 years old and he's the most food-crazy animal I've ever seen. Always has been. We feed him several small meals a day but it doesn't matter.

Thanks everyone!

Wet food or dry?  If dry can you get one of the toy balls that dispenses a few bites of kibble as the cat bats it around?  We used one of those for a dog that bolted his food, and it would keep him occupied for quite a while.

Their background can play a role, ie, if they were rescued from a feral litter. I have had and presently have cats who were from feral litters. They didn’t know when the next meal would be, so were in the habit of eating as much as possible. My previous cat was pretty much like that for his entire 21 years.

Some of this behavior seems to arise from boredom. Try distracting them by playing with them with a feather toy or something like that. That can help tremendously, to the extent that they forget about food for awhile.

The toy mentioned above, called an Eggercizer, is also a fun game. I feed them 6-8 dental kibbles in those. My two boys sit around every evening waiting for me to load them, and they then have to roll them around to get the kibbles out.

Stop feeding him, put him outside, let him fend for himself.