'37 windshield gasket

Ha! I have had the same problem! I have you tried to adjust your window hinges? Sometimes you can stop the leaking......sometimes you can't.
mine leaks on the passenger side, makes for a soggy glove box!
 
The whole shebang was a bad idea right from the start. As Felix says, sometimes the hinges can be adjusted in or out.
 
Adjust the hinges and make sure the drain on either side is open and has a hose that will carry the water out of the body. I have two 37s with Drake rubber that work just fine. Recently installed new windshield frame in 32 and had to carefully adjust then "help" the rubber conform to the body, after several weeks in the closed position, fits well now.
 
Making sure the drains are clean and hoses attached to the drain to carry out the water is key to a dry inside. Henry put those drains in there for a reason. Those windshields were guaranteed to leak right from the factory. The drain hoses go down into the cowl sides, so make sure the cowl panels are also clean to allow the water to exit..
 
There are six screws on each hinge that must be loosened to adjust the hinges. Two of them are inside the windshield opening. I had relatively good success by loosening the screws and getting on the sides of the windshield and shaking the whole assembly while pushing it the way it needed to go to line up in the body opening. Then I closed the windshield with the regulator and tightened the screws. It is not perfect, but the visible air gaps and wind whistle are gone.
 
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