Clint,
Here goes...
In a nutshell, what happens in meaningful stock market crashes like 1987 or (more importantly) like 1929?
In 2000, the S&P was down 9.1%. Magic formula was up 7.9%. In 2001, the S&P was down 22.1%. Magic formula was up 69.6%. In 2002, the S&P was down 22.1%. Magic formula was down 4.0%. So maybe that helps.
The whole idea is that you have a built in margin of safety so that if the market goes down like it did from 2000 to 2002 good businesses purchased at bargain prices will not go down nearly as much and may, in fact, go up.
As far as 1987 is concerned, the stock market went down 25% in one day. And that was pretty much it. If you blinked you missed it. So what would you expect a typical magic formula stock would do? Go down maybe 12%? What's the big deal about that?
I can't tell you much about 1929. That's even before my time.

. But as a general comment about crashes, it's ridiculous to plan an investment strategy around a possible event that happens every 50 years or so. As he says in the book your alternative is to put your money in a 10-year Treasury bond. Right now you'll get 4.5%. If you want anything higher than that, you're going to have to take some risks.
I noticed that Greenblatt's backtesting conveniently started in 1988 which bothered me a bit since that left out the 1987 crash.
He didn't "conveniently" start in 1988. He's using Compustat's point in time data base which goes back 17 years. Look, Joel Greenblatt doesn't need to manipulate data to sell us books in order to make money. He needs more money like I need more headaches. If you don't know anything about him, just trust me on that. Some extremely successful people get to a certain stage in life that they want to give something back to people. They truly want to help other people. That's all he's trying to do. If he were trying to make a lot of money on this, I could certainly come up with a better business model than what he's come up with.
Clint, stay away from this until you really "get it." Otherwise, there's no way you'll be able to stick with it. I suggest you read the book again. It seems simple because he writes like he is communicating with a 6th grader. But he is actually talking about some very sophisticated investment concepts. He wants this book to be for the public. But I don't think the public is going to be able to understand it. I think it will become a cult book among investment professionals just like his first book was.
Larry