re: #358 LudwigVanQuixote

Go Artscroll. It depends on what you are looking to do. Rashi is the basis of much Torah scholarship, meaning that one often starts with him as a first step in Yeshiva. Rashi has an encyclopedic understanding of the Midrash and a deep understanding of the Hebrew Language. He assumes a lot of prior knowledge. Of course the only way to get that knowledge is to dive in, ask yourself why he is asking what he is asking, and then look up the background material.

“What’s Bothering Rashi” is a good series that may help get the hang of the kind of issues that come up in the commentaries.

I also recommend a series called “The Midrash Says” for general read.