I'm about to curse and rant about a D&D thing. For those not up with the latest developments, here's an overview post I wrote pertaining to the upcoming Wizards of the Coast 5th Edition:
And here's the article I'm reacting to, a Wizards long term employee talking about rating rule book covers:
Now on to the unfocused blather. If you're not really into this, stop here.
So, there are the four Player's Handbook covers from AD&D 1 and 2, then Wizard's D&D 3 and 4. Firstly as to rating them and how to judge that, the answer is obvious. See also: most comments there. They get progressively worse.
The pictured 1st Ed cover was a typically sketchy TSR early product but it embodies everything good about the game, especially at that time. A bit DIY and then showing a party checking a map, cleaning off a sword next to dead monsters and looting treasure from a cool location. Also you come to this game in many ways ... but being attracted by a shiny book cover as you shop for something else - having never before entertained the notion of playing - is not one of them. And for people into the game already, the cover becomes all but irrelevant.
If you look at the industry insider article on this that I linked - many things are revealed, especially through his criteria for judging the covers. I think it not only shows why the older ones were better - but gives us a clear view into how the 4th Ed was developed and then failed.