I've recently been getting back into digital painting after a long time away from the tablet; BoardGameGeek is running a contest in a similar mould to the Assemblee event/contest that TIGSource ran a while back. In the first half (until halfway through December) artists provide graphics and art intended to be turned into board games, but while they can position elements on the board and decide what pictures are available for cards, tokens, player pawns and so on, they don't have any say on the game itself. In the second half, game designers take the assets produced by one of the artists, and design a game which uses the images the artist provided.
I love this kind of contest, for a couple of reasons. One is simply that I enjoy drawing and digital painting and designing graphics and so on, of course, but the big one is twofold. Firstly, there are a lot of talented designers around (or programmers, in the case of the TIGSource iteration) who just don't have the artistic ability to do their own graphics, and yet few people bother to try a Print-and-Play boardgame or a free amateur videogame unless it has nice artwork. Secondly, it's too often the case with competitions - both in the amateur-videogame and the boardgame communities - that games with nice art get rated better than they probably should for the quality of the game itself... and even if that isn't the case, people are far more likely to look at them if they have decent pictures. So running a contest like this means that people are more likely to get judged on the actual game, as the art isn't actually part of the entry strictly speaking.
Anyway, this time around I went with an age-of-sail theme for my imaginary not-yet-designed boardgame; you can see the WiP thread here. I'm actually quite tempted to do a second art bundle with a different theme once I've polished this one off, probably some time in the next week or two...