97 Cadillac Deville (Parking Brake)

Parking brake is not relaeasing when i put car into gear. I have to manually release it. Anybody know what the problem could be?

Do you have to hit the manual release underneath or help the pedal up with your foot?

Yes, what he said!

But also, if it releases but you have to help it up with your foot, then the return spring is just broken. It's very common on those cars. I've owned 2 1994 Devilles, and both have had the parking brake return spring break.

Well months ago, i was helping it up occassionally with my foot but now that isn't an option. The only way to get it up now is with the manual release.

Put some rags on the floor to catch drips and spray the whole mechanism down with WD40, 3in1, or some such. Worked for me for a while. What cured it permanently was a good soaking with Breakfree CLP.
FWIW
YMMV

The problem was deteriorated vacuum hose under the hood near the accumulator. The hose had whole in it thus causing the system to lose pressure to the point where it wouldn't release the brake when put into gear. Ironically, this is what was causing my a/c not to circulate through the vents facing me. You may have seen this in another one of my post called "A/C Distribution".