Art is like wine.
What matters is if you like it. The history and context and story can increase the enjoyment of the artwork or the bottle, but are not prerequisites to enjoying it. The problem arises when people think that education is necessary to know whether something is good or not. That’s why people stop trusting themselves. They look to Wine Spectator or Art Forum to tell them what they should like. This is a shame.
I am not saying you shouldn’t learn about the wine making process or the artist’s inspiration. You should. Just don’t sacrifice your taste in the process. Educate your taste.
Drink what you want. Then, learn how it’s made, the history behind the region, or even the personality of the creator to make your experience more enjoyable. Taste different wines, compare flavors, and you’ll develop your palette and be able to taste so much more than you could before.
It’s the same with art. Look at different paintings and you’ll start to see things you never realized existed. The brush strokes, the use of color, the subject matter. You’ll start to understand why you like different kinds of art and might find that you actually love artwork you previously dismissed.
People and magazines will always try to tell you what you should value. Whether you look at thousands of images or just the one in front of you, drink what you want.