Elmore's take on the Sutherland Dragon

This illustration by Larry Elmore is from a fairly obscure product, the manual for the 1982 adaptation of TSR's boardgame DUNGEON! for the Apple II+. It's on the last page, and is the only illustration in the manual other than the cover, which shows a B&W version of the box cover art by Jeff Easley. It may have appeared in another TSR product, but a Google Image search didn't turn anything up.

While much smaller --- perhaps a Sub-adult? --- Easley's dragon clearly shares many details with David Sutherland's Red Dragon on the cover of the Holmes Basic Set (July 1977), particularly the head - triangular, heavy brow, cheek "whiskers". Also note the V-shaped scales down the ventral portion of the neck, the slightly curved spikes down the back, even the shapes of the scales. 

Sutherland drew a similar B&W version of this same Red Dragon for the monster entry in the AD&D Monster Manual (Dec 1977) ---

Which was redone in color by Jim Roslof for the AD&D Monster Cards (1981) ---

A Red Dragon does appear as one of the monsters in Dungeon!, so Elmore may have been using one of these as a guide in order keep the look consistent between TSR products.

If you'd like to see the entire game manual, it can be found here at the Museum of Computer Adventure Game History.


You can also watch a 10-minute play-through of the game here --- Dungeon! for the Apple II

It had graphics like this screenshot, showing a Superhero versus a jolly Purple Worm ---

Update: As pointed out by John L in the comments, here is Bill Willingham's take on a similarly styled dragon, from the Moldvay Basic Set rulebook (1981). 

Monster Manual 1E artwork trivia

Chimeras - 1st print MM (left) vs 2nd print MM (right)

Over on the Acaeum, misterspock has documented several artwork changes that were made to the Monster Manual. The first is the Chimera; the original drawing by David C. Sutherland III (aka DCS III or just DCS) from the first print MM (Dec '77) is missing its wings, despite having an 18"/round flying move. The later drawing, also by DCS, from the 2nd print MM (May '78) has the wings added as well as other changes. Also altered were the Type III Demon and Nightmare.

An older post on Dragonsfoot by Paul Stormberg of the Collector's Trove provides some context for these changes:

"Dave (DCSIII) told me he didn't like some of the creatures he drew (Type III Demon, Chimera, Dinosaurs, and some others) as they had to be hastily done. DCS was a fast artist but it made his quality suffer. The Monster Manual was supposed to be done by Dave Trampier but he worked slowly and often quit and went home or to the local bar to blow off steam regardless of deadlines. Not so for DCS. He labored long into the night to get things done and sacrificed quality for speed when ordered to do so. Tramp was different, he was the golden boy for Gary and Gary did not push him on deadlines. Instead Dave was asked to pick up the slack.

When Dave got the Monster Manual blue lines from the printer he saw "this huge hole" in the document. There were no dinosaur illustrations, at all, just many blank pages. So that night Dave did all of the dinosaur drawings. He was supposed to be working on other things but crammed and speed drew things to pick up the slack. So a few pictures that had been hastily drawn by DCS, and that always bugged Dave were redrawn by him for later editions of the MM. It is the only book where he does this because it was never meant to be his project and the hastily drawn stuff bugged him so he just had to fix some things.

In the end, DCS was selected to be the Art Director for his work ethic and he slowly moved away from having time to create art. Ultimately he directed cartography at the company which you begin to see in fantastic maps like those in I6 Ravenloft."

Tom Wham is also listed in the credits, and contributed both classic "bestiary" drawings that blend well with the others (Beholder, Blink Dog, Herd Animal, Gynosphinx) as well as his signature cartoons (Giant Lynx, Mind Flayer, Giant Pike).

In addition to the altered artwork, later MM prints also added new art. Buried on the Acaeum's Monster Manual errata page is a list of the missing artwork in earlier printings:

First:  Ape (Gorilla), Centaur, Doppleganger, Dryad, Eye of the Deep, Fungi, Gar, Ghost, Hobgoblin, Intellect Devourer, Kobold, Men (Berserker), Merman, Mummy, Otyugh, Pegasus, Pixie, Purple Worm, Rat (Giant, Sumatran), Skeleton, Slug, Sprite

Second:  Ape (Gorilla), Eye of the Deep, Fungi, Otyugh, Rat (Giant, Sumatran)

Third:  Eye of the Deep, Fungi, Otyugh, Rat (Giant, Sumatran)

Fourth:  All pictures present.  Note that some monsters still do not have an accompanying illustration, but the Fourth print is as good as it gets.

[Note: the Ape (Gorilla) here should actually read Ape (Carnivorous)]

Most of these added illustrations are by DCS or Trampier, but the ones added to the fourth print are by Jean Wells (by herself or with DCS), whose name was also added to the credits on the title page.

Unpublished drawings also exist for several monsters that never received an illustration in the Monster Manual, including a Slithering Tracker and Giant Skunk by Bill Willingham, a Masher by Erol Otus, and an unattributed Shadow.

Update: Here's a screenshot of the DCS Chimera in the Blackmoor Supplement (Sep '75) that paleologos pointed out below:

Obscure Art Friday: Slithering Tracker by Bill Willingham

Slithering Tracker by Bill Willingham

     

Here's yet another piece of original artwork found along with the Masher, Drow Captain and Bugbear Chieftain. This one illustrates the Slithering Tracker from the Monster Manual, which is described as "transparent and almost impossible to discover" and having a "semi-fluid body" that can "flow through openings as small as a rat hole or a large crack under a door". I hadn't really thought of the Tracker as one of the "clean-up crew", but this illustration makes me think it's related to the oozes, jellies, and puddings. Like the Masher, this is another monster that might have gotten more attention with an illustration. I always assumed there was no illustration because it was invisible!

I hadn't seen this piece until recently when I happened across it on a page at Tome of Treasures. According to the original post on the Acaeum the ebay lot where these were found also included a Giant Skunk by Willingham and an unattributed Shadow, each of which was intended to be added to the Monster Manual (but never were). I haven't come across scans of the Giank Skunk or Shadow anywhere.

If you'd like to see more Willingham art, there's a recent thread over on the OD&D Discussion forums dedicated to his work that has some scans and links. In the first post of the second page I started compiling a bibliography of his work.