Art of the Genre: The Halflings of Jeff Dee

I was playing Keep on the Borderlands this past week, certainly one of my all-time favorite modules, and as I flipped through it I came across a Jeff Dee illustration that had a Halfling in the background. As two weeks ago I’d done a piece here on BG called ‘The Top 40 RPG Artists of the Past 40 Years’ AND had left Jeff off that list, I couldn’t help but stare at the image and wonder why I had done so.
Certainly people in the OSR had raised a big fuss about Jeff’s lack of ‘love’ on my part, and for good reason. He could have arguably made the list, depending on how you viewed the industry as a whole. Add such a view to the fact that Jeff has been a tireless game designer, player, and advocate for the industry of RPGs since I was in grade school, then he could almost be grandfathered in just for trying so hard. I guess it would be like a Lifetime Achievement Oscar or something.
Whatever the case, I sat there looking at this great little Halfling and couldn’t shake the feeling that of all the artists to ever do these little guys, Jeff was hands-down the best in my opinion, and here are the reasons why.
One: Jeff is a gamer, and as such, he has an inherent connection to how gamers see themselves, and with that, how gamers see their characters. Certainly, the thought of a Halfling is appealing because of Tolkien, but not necessarily the thought of Bilbo Baggins. Sure, we all love Bilbo, but do we love the Rankin/Bass version as a representation of our player characters? I doubt it.
Two: Jeff drew from a comic book style and therefore his lean lines for humans and elves spilled over directly to Halflings. Gone were the pot-bellied and cheery pipe-smokers, who were in turn replaced by ‘little men’ with ripped chests, chiseled faces, and weapons and armor that looked incredibly formidable.