I've come this far and can ignore this painter no longer - Clyde Caldwell. If Larry Elmore is fundamentally a painter of landscapes and Keith Parkinson a painter of trees, then Clyde Caldwell is in pure essence a painter of womanly thighs. The teenage youth I was blessed him for that.
Some nice orc thigh action in Princess in Peril, from TSR's Amazing Stories calendar published in 1986. Amazing Stories was a well know sci-fi pulp fantasy magazine that started in the 1920s which TSR bought in the 1980s and then finished driving it out of existence.
You can see Caldwell's work at its best and purchase prints at his website, https://clydecaldwell.com.
Clyde Caldwell was one of the four great oil painters from TSR's Pit days, and my least favorite of the bunch as I poured over D&D art. Caldwell did some sci-fi works for TSR's Gamma World, but is most known for his high or epic fantasy works featuring scantily clad women with exposed cleavage and thighs - really well done thighs. However, as a teenager who put a lot of time into Dungeons and Dragons, my chief love and concern was creating maps. And maps make me think Caldwell. Clyde Caldwell's best paintings for TSR are the covers he did for the D&D basic rules Gazetteers. As a collection of paintings for the same product and theme, I would say they are the best art work to ever come out of TSR. It's not just that they all include maps as part of the overall composition, it's the variety in each painting that evokes senses of place, culture, adventure, danger. It is the use of color across each painting, the harmony of disparate parts coming together. The brushwork and human anatomy are good, noticeably better than his earlier work. While figures are fairly static, there is still a dynamism in the flow from one image to the next. It's great stuff. And the women are all alluring.
Below are three of the Gazetteer covers I've taken directly from Caldwell's website. None of these are my favorites, but they give an idea of the collection as a whole. I'll play a little trick on myself and drop the first Gazetteer cover Caldwell did, replacing it with Gazetteer 3, Principalities of Glantri. The first Gazetteer cover was Grand Duchy of Karameikos, and I'm using it for a later post on Caldwell's top tier works.
Gazetteer #3, The Principalities of Glantri, published in 1987
Gazetteer #10, The Orcs of Thar, published in 1988
Gazetteer #9, The Minrothad Guilds, published in 1988
Good works, but not my favorites. Those come here, in the order of third, second and first faves. The images I'm able to find are smaller than those on Caldwell's website, and are the actual gazetteer covers with titles, trade marks, etc. We have The Five Shires, The Northern Reaches, and The Elves of Alfeim. The last two feature womanly thighs in classic Caldwell fashion. Note the colors below and above. They work so well as a collection. I also love his more worldly take on halflings (hobbits) and his more aggressive take on elves. For the Northern reaches it's the colors, and the more historical Viking images juxtaposed with his awesome female warrior who appears in classic Caldwell fashion and adds the fantastic tone to the composition.
Gazetteer #8, The Five Shires, published in 1988
Gazetteer #7, The Northern Reaches, published in 1988
Gazetteer #5, The Elves of Alfheim, published in 1988
Higher resolution image of Clyde Caldwell's The Elves of Alfheim with more accurate colors
Beyond the Gazetteers I'll add a few of my other Caldwell favorites, more typical of his style from early works right up to the present, although he did do covers for TSR's Ravenloft adventures that employed a similar composition style to the gazetteers around the same time period. The major changes I see over time in Caldwell's work is moving towards harder, more defined lines and more detail. I don't think his composition and capture of the human form was ever any better than the several years he did the gazetteer covers in the later 1980s and early 1990s.

Pot Luck, a painting I especially enjoyed from my teenage years and found inside the AD&D 2nd Edition Player's Handbook. The painting originally appeared in the 1986 Amazing Stories calendar, which was a perfect fit considering the pulpy subject.
One of Caldwell's famous and iconic Dagon Magazine covers, Alerelean, from issue # 94, published in February of 1985.
Captured! One of my favorite Dragonlance paintings by any artist. I believe it first appeared in a calendar collection. Yes, it was TSR's 1988 Dragonlance Calendar.
This is a personal favorite and guilty pleasure due to the female character with staff. It's by no measure Caldwell's best painting and is not well know. For me there is no way around it, the gal is just sexy as hell. This is the cover to the D&D adventure Earthshaker! by David "Zeb" Cook. I'll note that the female figure bears a strong resemblance to one of Larry Elmore's common female subjects and muses, who I understand is Mrs. Elmore, his wife.
Earthshaker!, adventure published in 1985
I'll add one of Elmore's examples for comparison. I believe the title is either Fools Gold, Gold Mountains, or simply SnarfQuest. It was the cover to Dragon Magazine #132, the April Fool's issue for 1988. I love this painting so much that if I can ever find a decent copy of it I'll do a post dedicated to it alone. Another interesting tidbit on Elmore is that he now paints figures from real models, whereas his earlier works, which often included included his wife, he painted more from his inner vision. It's no secret that his earlier figures are better. Please don't take any of this as fact. These are items I vaguely recall from a The Art of the Advanced Dungeons and Dragons I had over thirty years ago, and in more recent years Scott Taylor's blog, Art of the Genre.

Fool's Gold, from Dragon magazine #132 published in April of 1985
The character in the middle is Snarf, from Elmore's cartoon SnarfQuest that featured in Dragon Magazine for many years.
Hands of Doom from the 1987 Dragonlance calendar.
Finally, here we have what I think this is one of Caldwell's more ambitious paintings, and one of his best to boot. Hands of Doom depicts the tragic characters of Kitara and Lord Soth, and is another of Caldwell's paintings from a Dragonlance calendar. Caldwell or his fellow painter from TSR's Pit Keith Parkinson created the unusual helmet for Lord Soth, making him one of D&D's most recognizable villains. The painting also gives a bare calf instead of thighs.
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