Art of the Genre: The Top 10 TSR Cover Paintings of All Time

I’ve spent 30+ years looking at RPG artwork and I’ve yet to get tired of doing so. Sure, there are days when I wonder how the fantasy art world went to hell, but those are few and far between, as there are enough great new artists that still manage to inspire me in the mix of things [yeah Cynthia Sheppard I’m talking to you].
Nonetheless, I did begin thinking about well-aged TSR art this past month when James and I started digging in the nostalgia mines of old boxed sets. It prompted me to consider just what a ‘Top 10 list of TSR cover artwork’ would look like.
And to be clear, I wasn’t thinking about D&D in particular, but simply TSR catalogue stuff, which of course puts any artwork post WotC acquisition out of the picture. It does, however, allow for the additional inclusion of other games, although as I comprised this list I found it nearly impossible to include them. D&D, as it should be, dominated the RPG landscape from the mid-1970s, and thus is the bag of holding that any role-player will go back to again and again.
There are so many ‘things’ that could go into the making of this list, but for today I’m going to go with my gut. If I had feelings for it, it gets considered. If I know a lot of people owned it, it gets considered. Other than that, I don’t really have much to lean on other than the fact that this is what I do. I deal in old art. I buy it, I sell it, I broker it, I contract for it, I agent for its creators, and as you can see here, I blog about it. My only regret is that I wish it paid more, but since when does living your dream always to come with luxury?
That said, one name found on most RPG art lists these days won’t appear here because he came too late, and frankly, his greatest recognizable cover was done not for TSR, or WotC, but for Paizo. Yes, this means no Wayne Reynolds, but that is how this list is going to roll, so without further introduction, I give you my personal list of ‘Top 10 TSR Cover Paintings.’