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In Shawshank Redemption, Andrew Dufresne ordered the pickaxe through Red, which he then used for 19 years to pick a hole through the wall.

Did Andy order multiple pickaxes? Its seems impossible to drill a hole for 19 years with one pickaxe.

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Great question! This isn't discussed at any point in the movie, but in the Stephen King novella Rita Hayworth and Shawshank Redemption which the movie was based on, Andy did order multiple rock hammers. From the story:

Time continued to pass - the oldest trick in the world, and maybe the only one that really is magic. But Andy Dufresne had changed. He had grown harder. That's the only way I can think of to put it. He went on doing Warden Norton's dirty work and he held onto the library, so outwardly things were about the same. He continued to have his birthday drinks and his New Year's Eve drinks; he continued to share out the rest of each bottle. I got him fresh rock-polishing cloths from time to time, and in 1967 I got him a new rock-hammer - the one I'd gotten him nineteen years ago had plumb worn out. Nineteen years! When you say it sudden like that, those three syllables sound like the thud and double-locking of a tomb door. The rock-hammer, which had been a ten-dollar item back then, went for twenty-two by '67. He and I had a sad little grin over that.

Then, from the end of the novella:

And, of course, he had the rock-hammer. I remember thinking when I got him that gadget back in '48 that it would take a man six hundred years to burrow through the wall with it. True enough. But Andy went right through the wall -even with the soft concrete, it took him two rock-hammers and twenty-seven years to hack a hole big enough to get his slim body through four feet of it.

So in conclusion: Andy used two rock hammers to escape from the prison.

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Good find Andrew, I knew one rockhammer was not enough to drill such a big ole –  Firee Mar 28 at 12:40
    
@Firee If I'm reading things correctly, Andy doesn't receive his second hammer until the same year that he escapes. Essentially he dug almost the entire tunnel using a single hammer. –  FreeAsInBeer Mar 28 at 21:13
    
@FreeAsInBeer it's a bit confused, but apparently he takes 27 years to escape, and the first hammer breaks after 19 years. –  Lohoris Mar 28 at 23:51
    
@Lohoris Are you sure? Google says (quoted from Wikipedia) says he escapes after 19 years. Or did they change that just for the fil,? –  FreeAsInBeer Mar 30 at 2:40
    
@FreeAsInBeer I'm sure that this is what is written here "it took him two rock-hammers and twenty-seven years", just read up. Accurate or not, no idea. –  Lohoris Mar 30 at 9:39
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