If you live in the United States, yes. We waste so, so much food. Like seriously. You could go into a dump at "garbage time" (easy to figure out by just watching store employees) and grab an entire fridge-worth of food for multiple people. A lot of food banks or churches can do exactly what OP described as above; deem you for whatever reason not able to grab shit from their expired food section. Often than not, the food bank near me gives you a variety of cans that are more "baking goods" than actual food you can eat out of the can. 8 cans of applesauce is great for keeping full but not exactly nutritious and makes you feel like Steve Jobs on a fruitarian diet.

Dumpster-diving wasn't meant to be "insulting". It's seen as that because we look down at scavengers in America for whatever reason. When I was scraping by and jumping from place to place; dumpsters were literally the best place to get free food, free drinks and free beer.

Sadly, they lock them up, put security cams or dogs around the cans to prevent people from rummaging. Just gotta be smart.