Cobbler is decadent. It is all of the best parts of a pie, and nearly always includes my favorite type of ice cream, namely vanilla. A pie can be great, particularly if the crust is well made of delicious ingredients, but most often, the crust is kind of bland and very difficult to cut with a fork. In this, cobbler which has the delicious crumble topping but none of the inconvenience of the crust is clearly superior. The topping of a cobbler is always delicious, and its crunchy texture contrasts well with the gooey content of the fruit/syrup. I will eat cobbler much more frequently than I will the same flavors of pie, and I don’t have a great reason for that. A berry cobbler just sounds very appetizing. Peach pie…meh. Peach cobbler? Great!
The first cobbler I really remember eating was on a river trip in the Grand Canyon, and that may be where some of the added positive association with the dessert comes from. It is also something I will go out of my way to eat; though, it is almost always what I call spontaneous cobbler. There will be a moment in which I suddenly think man, cobbler would be excellent right now, and I have to go get it.