Keep on the Borderlands Alternate Cover Art - Process
I was approached a while back to do my take on the Jennell Jaquays cover art for her iconic module The Caverns of Thracia. Mine's the first one you can see in that post. I liked how that turned out and I liked the process, so I decided to have a go at redrawing the even more iconic cover art of module B2: The Keep on the Borderlands.
As I was posting work-in-progress shots and musing on the original artwork on Discord, there was a suggestion that I write this up into a post and so I have.
Studying the original cover

The place to start is, of course, by actually looking at the image I am to recreate. The original artwork is by Jim Roslof, and at least for my money this is the best work he's done for TSR. The vivid and bright colors (though a bit oversaturated in this specific scan of the image) along with the very specific 70s fantasy S&S stylization of the outfits the figures wear just makes it stick with me.
Composition
The composition itself is fairly straightforward - it's a fight between some adventurers and some...orcs? Hobgoblins? from the Caves of Chaos. In my own piece I ended up simplifying it for the different format of my illustration, and removing several of the figures or changing them in some ways.
The important element of the composition are the elven archer, the fighter locked in a duel with an orc, the orc that is shot down by said archer, the strange gnarly tree on the right side of the image and the rocky, pastel and almost desert-like hills that form the background. For me the two figures fighting on the lower level are not as important, which is why I ended up dropping them.

I decided to do a very rough sketch study of the original, identifying those elements and this study is also where I really settled on limited color palette for the piece - more on that later in the post.
Character design and outfits
As I said above, the other thing that stands out to me are the clothes and armor worn by all the subjects in the piece. Everyone, including the orcs, has very stylish decorative elements on them - metal necklaces (notice the mirroring ones between the elven archer and the orc being shot), wide, almost pro-wrestling sized belts around their skirts, horned helmets for the evil guys, the tight spandex of the elf. The warrior with the sword, the orc being shot and even to a degree the elf also all have these straps on their clothes, again giving it a very 70s Sword & Sorcery vibe.
While others have rightfully pointed out that KotB is in many ways a frontier Western story, and Gygax himself kept banging on about "Medieval fantasy", whatever he thought that meant, that's not really what we see on the actual image.
Yes the rocky hills and boulders suggest a more desert-like setting that could be read as Western, and the elf's cowboy boots also add to it, but everyone else is dressed like a pseudo-historical barbarian from the ancient middle east than anything medieval. These warriors look like they came out of a 1950s and 60s Sword and Sandal historical epic, rather than the RenFair aesthetic more prevalent in a lot of D&D. Hell, put on a bit more black leather and some fetish gear on these guys and this image might as well be set on Athas!
For me, this is very close to peak fantasy art, and also specifically this image evokes the same feeling I have when I look at the work of Peter Mullen
Settling on a style
So, let's actually wind back a bit before I decide to do the cover of B2. I was trying out a more flat and cartoony style for an illustration, but I had not quite settled on what that illustration would be.
Some of the pieces worked fairly well on their own like this one:

Others didn't quite land:

Around here is when I settled on The Keep on the Borderlands, and quickly realized that this specific style would not work for that composition and image. So it was time to pivot and experiment. I settled on just redoing the image of the elven archer (like I stated above, one of the key elements in the composition), as that is who the eyes naturally get drawn to when looking at the image at a glance.

This one has an appeal to it, I won't deny, but it also would not work well for the whole image. I tried to mess around with a colored line instead of black, but that didn't really land either. The colors also were getting lost - I like the warm and sun-bathed tones of the original image and wanted those in my own version too. It was still supposed to be recognizable as the cover for the same module after all.
This is when I decided to use the limited color palette of yellow, orange, magenta and blue to color in the composition sketch I had done a few days prior (see above). And that felt really right, it was bold and graphic and captured the spirit of the image perfectly.
Another go at the archer and, yes, this confirmed the color palette is what I was going for!

Now that I had that sorted, the next step was the actual stylization proper. I had seen several artists that I enjoy that use a sort of foam roller to create shading in very graphic and stylized pieces, and wanted to see if I can recreate that with a sponge (in short - no. I need a roller), as well as experiment with other shading options - stippling, be it black or colored, as well as simply using a black pencil.

This piece of paper was the result of all of this. I used acrylic paints to form the image and then just used the various shading techniques on it. The stippling did not look good and was way too time consuming, the foam was hard to control even if I liked the effect, so I ended up settling on the pencil. It picked up the underlying texture of the paper itself and created a nice bit of grit and noise which contrasts well with the very flat blocks of color.
I also settled on using watercolors for the final rendering, rather than acrylics, as the paints I had would leave a bit more texture than I wanted out of the solid colors, while the watercolor and its lower opacity created more interesting tones and nuances while keeping the surface flat.

This was the final test for the style. Flat color blocks in the minimal palette, black pencil for shading and patterns, and then black ink and white acrylic marker for outlining and defining shapes further. It looked good and it looked right, so it was time to start working on the actual piece.
The reason I went through all of this is to underline the iterative process - sometimes things just click right on the first go. You do your first sketch and it is perfect. But often they don't. You need to sit with the image, work on it, decide on what it is you're actually trying to do, and do your current skills allow you to do it.
Drawing the illustration
With my style, composition and materials all settled on, I got a piece of paper, taped it to a board for ease of handling and sketched out my composition. I used a 4H pencil, which is very hard and very light, and leaves virtually no residue on the paper because of that.
Using such a hard pencil has its downsides too - if I am not careful I can actually create dents in the paper itself, but the upside of it leaving very faint marks is worth it. And it was important that the pencils be fairly light, because even with the added texture at the end, I am using watercolor paints and they will not cover it up, as they do not have that opacity.
Since I was using only four colors with no blending, layering or indeed any other mixing between them, it was simply a matter of going around and filling in all appropriate things with the appropriate color. I decided to do them in order, starting with yellow, then orange, then magenta and finally blue.
Here is how that process looked. NOTE: You can open the images in a new tab to see a higher resolution version of them.

Yellows all filled in and starting on oranges.

Oranges now also all filled in, and you can start seeing the actual outlines of the figures.

Magenta is now filled in. You can see how little blue actually is in the picture.

With the blue all the base colors are now done. The image, while obviously lacking any details, is readable enough at this point which is a good sign I've made the right choices in which colors go where.
This was the most nerve wracking and most precise step of the whole illustration. While the detailing took almost equally as long, it was a lot easier to do. With the watercolors I had to make sure I do not let any paint go where it did not belong, as the lack of opacity means that any paints layering on top of each other will instantly stand out. Some bits here and there I can and did edit via the use of black and white, but any big spots would be impossible to correct.

Now came the fun part, the detailing! I started with the pumpkin-headed Bugbear (I had to put one in there!) being shot by an arrow, because I already had that one rendered during my style exploration earlier, and so it was kind of a freebie. I will present some more work-in-progress shots, as to me it was very satisfying to see the image slowly emerge out of the soup of flat colors.



After this one the image was 99% done. That is where I usually stop and leave it for a day, give my eyes time to look at it as a whole once more and ideally have a second pair of eyes (usually my partner) look at it too, see if anything stands out as missing.
The only thing I decide was to add some white to the clouds in the background, which I ended up having to do with acrylic paint as none of my white pencils really did much of anything on these light and bright colors. With that, the finally image was done:

Conclusions
This was a really enjoyable process, and I am already thinking of other potential covers I can redraw in this style. In general I have been wanting to move away from my half-hearted attempts at more naturalistic stylization and back to a graphic, cartoony and generally more stylized look. It has been quite a few years since I have worked in that style, and even in this image you can see that there's plenty of considerations for anatomy and pose.