Cucumber Quest by Gigi D.G.
In the world of Dreamside, Cucumber is excited to be finally going to a school for magic while it's his sister Almond who wants to slay monsters and do other things inspired by her Saturday morning cartoons. And it looks like Almond will be getting her wish, the Nightmare Knight is causing havoc across the world and Cucumber is the chosen hero who must defeat him and his Disaster Masters. But the Nightmare Knight and his minions seem oddly savvy about all of this, as if they've had to do this before and that they've learned from it.
To continue with that train of thought from the intro, there have been some moments in the comic which are making me wonder if this comic is also set in a video game, one that has been played so many times that it's characters have either become sentient or started glitching. When I first started reading the comic I thought that the black boxes of explanatory text, with certain words highlighted, were merely a stylistic choice and that the story was mocking over-played RPG set-ups but now I wonder if those boxes are supposed to be literally what the characters in the story are seeing. I am hoping that this theory doesn't turn out to be the case since it would make the story feel a bit less original to me. The idea that the characters are acting against stereotypes and tropes because that's how stories really play out (ie it's completely, 100% because of their own choices) is more amusing than if it's partially because of their own personalities and partially due to an outside force (the game) creating them that way. There are so many fantasy and video game parodies out there these days that it's hard to tell which one there are more of but I feel like I've seen more video game parodies than simple fantasy parodies and those parodies are usually much more derivative (her Hiimdaisy comics even set a trend that you still see everyone now and then). After you see two or three it's much harder to be engaged by one without thinking about how many times you've seen the same damned joke.
One thing that hasn't changed from the very beginning is the rather distinctive art style in the comic, it's a lineless, very blocky-style of coloring and shading that I rarely see used for a full comic (the only other one I can think of off the top of my head is Bladerdash but it's much less dramatic there). Normally I'm not a fan of art that uses really simple shading with basic shapes but it really works here, it's helped by the fact that Gigi uses color with aplomb and isn't afraid to use an odd color for shading and highlight which is should be enough to convince any nay-sayer that the simple style isn't for lack of skill but on purpose*. The character designs are also lively and varied and if the backgrounds aren't the most detailed then that's okay, the series tends to make more use of mood lighting even when there's a clear background just a few panels earlier. At this point I still don't have any intention of dropping the series but I do hope that it somehow draws me back in so that I'm enjoying it as much as I did in the beginning.
*heck, I wish this comic had been around when I was in high school and learning the very basics of shading and color theory, this would have been a great example of how to use complementary colors to create shadows which I could just never wrap my mind around in school