First, thanks for this topic, because it finally pushed me to organize all the cover art for my games in one place. I think just browsing it every so often (even once a week) helps, and I should have done so before.
Cover art is something I procrastinate and only really attack once major bugs seem fixed. I have to admit I just slapped stuff together with stick figures for some of my works, and I really, really want to upgrade those. I’m proud of the works themselves (Problems Compound, Ailihphilia, Very Vile Fairy File) but I don’t want to link to the cover art! Topics like this remind me that new cover art alone would be a reason for a re-release.
I was really happy with @severedhand’s cover art for 3(!) IFComp entries in a row. Especially since one was about baseball and I remember insisting on a detail or two that might’ve made his eyes roll. And the whole game product was rushed. But I really liked it, and it gave me a late boost. I do however think his cover art for Shuffling Around and Threediopolis were a great example of me asking for an idea and having to say, okay, I have a max of 3 or 4 important details I want the reader to see. Certainly his questions helped me figure what I needed. Even something like making sure an image or font set was public domain helped. Being able to go back to these images has been surprisingly helpful, and it reminds me of questions he had and I can ask myself.
@J_J_Guest is the only other person I asked do cover art and I was also very pleased with the results!
Having some insight into their process helped me think–and probably will help me think going forward–about what I really wanted to do. So if he has the time and motivation, and you are wondering if you should ask, and he is open to offers, I recommend it.
As for my own cover art, I had people tell me my stick figures can be a riot sometimes, but I’d like to go for a subtler less flippant kind of humor. I think having nice cover art in place lets me sort out a few additional details, and that was the case for my collaborations.
Too often it seems like I whip up cover art at the last minute, but I think it’s best if I have something–anything, even a rough draft or notes on what I want–a month in advance. I’m not above taking vector art or whatever. With A Roiling Original I think @HanonO suggested the font, and the cover captures an early puzzle that isn’t very spoilery, as hopefully it’s not too tough.
So I think bouncing cover art off others is really helpful!
I’m pleased with my recent efforts at cover art, while recognizing they’re not earthshaking. Fivebyfivia was just some hand-written nonsense until I had the idea to kind of anthropomorphise chess pieces, and I do like the result. I was able to find a perspective checkerboard which I re-colored with MSPaint(!) … I put it into a monochrome bitmap, then I cut/pasted simple shadow drawings of a king, queen and rook onto the board. So I think I got that retro feel without “ha ha ha I wasn’t trying” vibes. Fourbyfouria, I found vector art and using fills was not bad. For Walking Into It, I was upset nothing popped up, but then I figured something with a week left in IFComp, and I was pleased with how the cover blended into the game. Then for my two EctoComp games, I found some good stock images and textures which made me happy. With Weary Eerie Way it was a blimp, and I did some original drawing, but I had fun putting Psyops Yo together, with the gradient, and the autoshapes for the un-suns.
So I’ve gotten to feel comfortable with vector drawings or free stock images/textures. And I feel I can reel them off. But I know they’re limited!
I want to move to actually drawing my own stuff for good, as I want to do more drawing in general. And while my favorite bits of my games are the weird stuff where hopefully it’s a bit odd to picture something and I wouldn’t want to restrict the player’s imagination, I still want to get across good cover art to make a good first impression. That’s something I’ve fought with in general–I’m suspicious of people who are all first impressions and nothing else, but I want to give people a reason to give my stuff a chance. You want to underpromise and overperform in general. But you can’t be a blank slate.