Not quite the worst painting ever....

...but still not stellar. The very very VERY worst painting I've ever done was in first year college. The duotang dragons and craptastic cartoon bunnies I did in highschool were better than The First Year College Landscape.
We were supposed to do a landscape, but the painting teacher we had believed in the Figure-It-Out-Yourself-Because-I-Don't-Get-Paid-to-Teach method of teaching so the results for many of us were... spectacular. I'd never done a landscape before and decided in my wisdom to haul 500 pounds of easle, canvases, oil paints, brushes etc down into a ravine to paint down there. I had visions of doing a beautiful green meadow, maybe with some sunlight dappled through the textured trees. You'd almost be able to feel the breeze flowing through and hear the birds chirping. Maybe one would even land on your shoulder and tell you what an awesome painting this was! So beautiful, so peaceful, so not-in-this-lifetime.
I'll just start by saying I honestly had no idea of composition. Or even how to paint- particularly with oils. So there I was sweating and attracting mosquitos because I'd hauled so much junk down a 'gully'. I tried not to think of hauling it back up as I set my newly resized canvas up in a lovely valley between two hills. My prof took marks off for canvases that weren't the exact size and I didn't have the money for a new one 'the exact size', so I took a larger one I had already, and tried chopping it down to the correct size. First mistake. It was all wobbly and the canvas didn't fit properly on the stretcher any more so the bottom wrinkled up. I'd deal with that later- I was going to paint the world's best painting and re-stretch it later! Too bad I didn't realize how dim that was. How do you re-stretch a canvas that is covered with wet oils paints?

For some insane reason that even today eludes me, I decided to paint one of the hills I was standing between. The steep one, with no grass, just brown eroded earth. Don't ask why. I was standing in a lovely valley between two hills with a path that went off in the distance where unicorns ate candy and gave rides to happy little girls who can paint, but I chose an almost empty dirt hill to reproduce.
I feverishly worked away on painting the entire surface of my canvas in... brown. Not even a nice brown. A brown I made by mixing 14 other colours together and turned them into mud. Actual mud would have looked better. I didn't even put a horizon in it or have a vanishing point, not even a whisper of the sky. I had painted a flat, brown wall. Becoming frustrated because my beautiful painting already looked terrible and I'd only been working 30 minutes (with all the hauling it was more like 2 hours, but hey), I started on the trees. Only problem was my POV was about 5 feet away from the tree trunks and at that level there were no branches or leaves. Just brown trunks. Again, another winning design choice. The brown tree trunks melted in with the mud-brown background. Solution? Toxic yellow! That'll work! Nope, still looked terrible. Gave up on the trees and moved to the ferns. The paint was quite thick by that time and I didn't know how to make my new paint stick so my green ferns were more brown than green. Solution? MORE toxic yellow plastered on!

With no sky in the painting, you didn't know it was a hill- it was just this awful brown expanse with some toxic yellow that might have been regurgitated by a penguin. It was like looking at a canvas of nuclear waste. I should have claimed it was and might have even got away with it as the bottom half of the painting was sagging and wrinkled due to my stretcher 'fix'.
Obviously I didn't get a very good mark- it's quite possible I failed that assignment! One clever little monkey in my class sat down with a Bob Ross video and her painting turned out great, as did her mark! Curses on people with brains!
And that's the story of the worst painting I've ever done (so far), but even still I wish I hadn't thrown it out. It's polluting and leeching its toxic-ness (a la that melting guy in the first Robocop movie- the one who fell into the nuclear waste) some innocent landfill somewhere when it could be hung with pride in my house where I could laugh it every day. At the time, and for years later I was so ashamed and down on myself for it. That being said though, I'd love to have that painting now! The best thing I've ever learned is how to laugh at your own terrible work, and truly appreciate shite. What a pile of excrement, and how awesome!