Hey, well I'll get straight to the point since this problem has caused me to hate this car more then I already do.

Anyways my father owns an 95 Olds Cutlass Supreme SL 3.1L, anyways for the past few months when shifting from park to drive the button on the shifter is hard to press (eg we sometimes have to literally take a hammer to get it to go in), but when the car is off and we go to shift it's fine, so anyone got an idea of what the problem might be, my bud thinks the tranny is on the way out... again.

you mean that button that lets you take it off Park position?

i don't think the tranny is your problem..

First thing put the hammer away. A hammer is only useful for bodywork on cars. My first inclination would be to check the shifter itself. I'm betting the problem is in there and not the transmission itself. Can you park it in neutral with the parking brake on and remove the key? Does the button on the shifter still lock up? Does it only stick in park? Maybe the parking pin?

^ I think I said the shifter button doesn't lock up like that when the car is off (aka not running), and I don't know of any cars with an automatic that'll start in neutral let alone shut off...

The other thing I forgot to mention, theres been a few times the car is in park (we generally don't use the parking brake) and it's started rolling once we release the brake...

And how can it not be in the tranny when I said it only does that when the car is running?

Yes the shifter button.

I thought all automatics can start in either Neutral or Park..at least my Holden Commodore does.

Think it can be from damage from using the shifter as a parking brake. I heard not using the brake to park can damage or shorten the life of the transmission.

The car only provides your power steering and power brakes when running; are they part of the transmission too?

Then going by that logic shouldn't it be even harder to shift when the car isn't running?

Hmm, my Scout II, Chevy truck, and Lincoln Town Car as well as the parent's accord, all autos, will all start and shut off in neutral. Most of my cars are manual though. Did you actually check the Cutlass?

If it starts rolling once you release the brake then I think it points to the transmission not actually engaging in park. I still think the problem might be in the shifter mechanism itself, but with the additional information it is looking like might be in the parking pin. I would start with the shifter mechanism as that will be easy to check and cheap to repair. Then move to the tranny as that will be harder to check and more expensive to repair.

In the meantime, if you can in fact start and shut off in neutral. Do so. You might be unable to remove the key though. I would defiantly use the parking brake as it seems Park is unreliable regardless. I might even go so far as the chock the wheels.

Care to tell my father that lol, he's already caused the parking brake to seize once by not using it (it's an automatic it doesn't need it (quote of him...)). I gotta go move the pos in a minute and I'ma see for myself if it'll start in Neutral.

Edit: okay... well it does it when the car is off too (I went by an unreliable sources word, my mothers...), it will not start in neutral and anyone care to tell how to take the shifter apart?

Not if there's some sort of lock that only engages when the car is started. Either way, you've discovered that it isn't that.

That is going to vary from car to car a lot. Either try a Cutlass website for that info or buy a Haynes or Chilton manual. Be sure to see if it has the info you need before you buy it or just look through it for the info at the store. My guess based on other cars is some type of set screw holds the shifter handle on the top and to get to the bottom requires removing some of the trim or console.

Be honest to yourself about your own mechanical abilities. Ask yourself if this something you can do yourself. Also if you have to purchase tools that you will never need again it may be cheaper to take it to a professional.