If you get a lot of specialty items (like faux cheeses and meats) it won’t go far. If you shop like normal but just skip the animal products it’ll almost surely be cheaper than regular groceries. You can make your own seitan very easily, there are many YouTube videos showing you how. It’s just a simple dough that is washed and kneaded to develop the gluten. You can also make your own tofu, but tofu is dirt cheap unless you get fancy stuff so I recommend just buying it.
The princess bride, mostly because everyone my age won’t shut up about it. By the time I saw the movie (I think I was 16?) it was like watching a string of cheesy memes.
Also, it’s a wonderful life is so frustrating and depressing, the “happy ending” just doesn’t cut it.