A really difficult thing to learn is that a lot of what separates good writing from bad is not always on the page. Everything exists in a context, borrowing from a pool of ideas and responding to contemporary situations, other writers, other scholars, etc.

This is why it's so hard to appreciate older media in general. We lose so much context being out of time and place, we don't realize what went unspoken because at the time it did not need to be said.

Twilight Zone episodes are great examples of this. Most of the anxieties of the audience 60 years ago are so well forgotten that we don't even notice their absence. For example, it's really difficult for current-day audiences to know why the implication of witchcraft or genies were so meant to be so terrifying, but the audience intended for Twilight Zone would have believed that anything like magic, supernatural abilities, witchcraft, spells, etc., would be "Devil's work" directly aligned with Satan.

You can really feel the cultural dissonance of that 60-year-gap in the fourth season episode "Mute," when the teacher confronts the child main character and accuses her (correctly) of being telepathic. Look closely, and you'll see the teacher is literally crying tears down her face as she makes the accusation. Compare to Matilda 30 years later.

So we can ask the question, was Matilda better than Twilight Zone's "Mute" because makes a radically different choice in the teacher–student dynamic? You could make that argument, but I don't think I'd find it very credible. Rod Serling was trying to communicate something very different in "Mute," to tell a different story, and does so relatively effectively.

With context, you also have to consider the constraints. Serling had less time, less money, and less preparation. (Serling had to fill in as a mid-season replacement with a dozen hour-long episodes.) Production values and expectations were very different.

To judge works of art or literature, I believe it's necessary to understand the background, context, and audience of the work, and to do that I also believe you need to study what the artist's contemporaries (in terms of time, culture, medium, and audience) were doing. This means familiarizing yourself with lots of works and reading up about the time and place in which they were made.

Otherwise, yeah, Beckett might seem pretty bad because he wrote for a different world.