Now I've been really lucky over the years......helps that one con I went to every year had a huge art auction for their charity efforts. Mostly smaller local/regional artists that you wouldn't know (but should.....if they still painted)
My whopping three visits to North Texas has gotten me some larger or better known artists. I was able to pick up an original Doug Kovacs ink used in the original Dungeon Crawl Classics book (and all subsequent reprints IIRC). I've managed to pick up some Diesel prints which are simply HUGE. I will have to re-do the matboard for one of the prints as the upper left corner is messed up a bit.
On a side-note, if you can cut mat board well (I've done ok up to that one attempt), you can either cut plexiglass with a fine-tooth table saw blade or even have the big-box home supply store cut glass/plexi for you. Couple with some reasonably priced frame pieces ("chops") and you can frame your own art for probably less than a 1/4 of the price of getting it done "professionally".
Special note/plea: I was going to my favorite frame supply place online so I could provide link to you fine folks, only to discover that they've closed up shop/retired after 48 years in business. They literally closed up shop last Friday. If you have a good alternative please, leave me a comment so I can check them out.....I still have stuff to finish framing!
I also managed to pick up a Jeff Easley artist proof last year, which I'm going to hang by the trio of Elmore prints I picked up years ago at GenCon.
Now I've clearly thrown around a few big names who might very well be on people's wish-lists. I've got some pieces by some "big names" that might not be so big to other people, namely Jolly Blackburn and the Fraim Brothers. Now I've "showed off" Jolly's print (it is still one of my most prized possessions) and I know if talked about the Fraim Brothers, but probably on one of my other blogs.
I really do want to sing the Fraim Bros praises for a hot minute here, if not for the reason that they were the inspiration for todays post in the first place. Now if you read The Knights of the Dinner Table you've undoubtedly seen their work. The thing is these two brothers are.....prolific, AND they take reasonable commissions. I've commissioned them I think four times now to do character portraits for me and my (ex) wife's PCs, and I've been blown away. At $50 a pop, so worth it! Turn-around on their website is listed as 2-4 weeks, but every time for me was less than a week. The picture on the right was off their old website.....and one of my ex's PCs. It's subtle, but you can actually tell she's missing a finger on her right hand!
Now they only take commissions that "interest them", but what I think helps is to just let them go nuts. What I did was describe each PC in detail, but only a paragraph or so and made it clear that I'm looking for their take on what I gave them and not a graphical representation of what's in my head. I think giving the artist carte blanche and letting them know I'm not expecting a bunch of approvals and revisions is important. First, they are more likely to accept the commission, and second......well let's face it: You're hiring them for their expertise! There is no way I could have envisioned a better "picture" of Arainell (pictured here) that what they came up with.
Now I have smaller pieces from even smaller artists that I got here & there for a buck or five. I like the tables at the "Artist Alley", assuming the con has one, and if they're offering a small print for a few bucks or even some on-the-spot "Draw your PC for (usually $1-$5)".....I'm down. I'll pick up a badly printed piece of decent art or commission a cheap PC portrait in a heartbeat. I might only use the portrait for one game, but it's all good. This piece on the Left was a $1/60 second art piece of my Dwarven PC. All I said was "Male Dwarf with a big-assed hammer". I think she actually took about two and a half minutes, but who am I to complain. BTW you can find the artist (Tina Bongomo) here.
I actually have all of my RPG art, save one huge HackMaster Poster framed and up on my walls or on my bookcases. I'd guesstimate that it's a good 50/50 split between larger and smaller pieces. I've run into a bunch of folks that have said something to the effect of "I'd love to get some RPG art....but..."
....but nothing. I originally started this post with the intent of highlighting a single commission artist (well a pair of brothers, but still), but it got me thinking about RPG artists in general. I can tell you that outside of the rare piece at a FLGS (which is almost never for sale), you generally have to go somewhere the artist has the opportunity to reach a large audience....like a convention. If you can pry yourself away from the gaming table, and away from the dealer room, visit the Artist Alley. Smaller cons tend to put the Artist Alley in with the dealers and if you can find an artist self-publishing some RPG material you might find they have original art as well, though that's more a side thing for their table.