This question isn't as broad as it might appear at first glance. I've seen drawings of dragons, Dwarves, Trolls, and Hobbits by Tolkien, and I'm primarily interested in only a few other races. He was a prolific writer and artist, but he seems to have shied away from making too many illustrations featuring animals or people. Perhaps the only imagine along these lines that I have been able to find are these:

The Dragon Glaurung.
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Smaug and Bilbo.
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More Smaug. enter image description here

Even more Smaug.
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Bill, Tom, and Bert, the Trolls, with Bilbo hiding in a bush (left background), a bunch of Dwarves in sacks (left foreground), and Gandalf casting a spell (right).
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Bill, Tom, and Bert again, with a Dwarf in the foreground.

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Bilbo at home.
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The races I am most interested in seeing are as follows:

  • Orcs

  • Ents

  • Elves

  • Wargs

These are the races/species I am most interested in seeing, although I certainly won't complain if you find pictures of other races/species.

Did Tolkien ever draw any of these creatures and races?

  • I spent my last vote on this question but it was worth it :D – Often Right Jul 21 '15 at 6:49
  • Maybe elves. None of the others. – Matt Gutting Jul 21 '15 at 10:42
  • And I even doubt elves, given how reserved he was on the subject of elvish pointy ears. – Matt Gutting Jul 21 '15 at 10:43
  • +1 for including some of Tolkien's artwork in the question :-) – maguirenumber6 Jul 21 '15 at 18:35
  • @maguirenumber6 - unfortunately, he was better at landscapes than people and animals. – Wad Cheber Jul 21 '15 at 22:41

In addition to the Trolls and Hobbits you've already depicted, I've found illustrations containing men, elves, dwarves and a picture of Gandalf.

In Tolkien's illustration of "Laketown", you can distinctly see 6 men (and a further 5 in the far distance).
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In this image depicting the "Halls of Manwë" you can see a figure (presumably an elf) at the stern of an Elven swan-ship.
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This pencil sketch shows Gandalf the Grey:
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Another pencil sketch shows "Dwarves Marching and Smaug" enter image description here

Another pencil sketch shows some dwarves "At the Back Door" [to the Lonely Mountain]

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  • 3
    Gandalf the Grey or a coatrack? – Wad Cheber Jul 21 '15 at 22:40
  • 1
    @WadCheber - The picture is entitled "Gandalf" so I'd guess not a coatrack. – Valorum Jul 21 '15 at 22:41
  • 1
    I guess I just didn't realize how coatrack-like Gandalf was. Now I know. The next time someone asks me to describe Gandalf, I'll say "He's like a magical coatrack!" – Wad Cheber Jul 21 '15 at 22:42
  • Who knew? – Wad Cheber Jul 21 '15 at 23:03

No illustrations of men, orcs, Ents, or wargs (at least that I know of). The only depiction of Elves that I know of is the painting of Beleg finding Gwindor in the forest of Taur-nu-Fuin:

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