Does it work even if the strips of bacon are so long that they go up on the sides of the pan? Or should you cut the bacon in half in that case?

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For ultimate crispiness, cutting in half, especially the ones on either side of the pan, is helpful. Sometimes I do. Sometimes I don't. I guess it depends on how picky vs lazy you are. Optimally the press exactly fits the bottom of your cast iron skillet, but that can be hard to do. Most presses are a little smaller.

I also have a bacon pan that holds the bacon up and separated for baking in the oven. It makes wonderful crispy bacon, but takes longer (20-30 minutes). I have two of them. I generally put the bacon slices in every other slot to optimize heat getting to all sides and being extra crispy. For that reason I have two of these pans.

https://www.amazon.com/gp/product/B074PB752L/ref=ppx_yo_dt_b_search_asin_title?ie=UTF8&psc=1

That's a really cool pan. Thanks for the advice 😁

I'm looking at some presses that'll fit my pan too. I learned a lot about bacon today.