I highly recommend Draw it with your eyes closed: the art of the art assignment (published by Paper Monument) to all art educators. It's an hilarious account of the favorite/best assignments given to, or by, artists and art professors around the country. These are mostly assignments in higher education, where the trick is to give students open-ended assignments with enough room for personal expression and imagination, while still having them learn something. The embarrassing, kookie and sometimes inappropriate results had me laughing out loud (in public, no less) with the creative interpretations of students, some of which go very, very bad, along with the usual "happy accidents". Inevitably, sometimes it's actually the teacher who ends up learning a lesson (eg. "never give that assignment again", or "only use that with grad students"). Covering all mediums, the book offers many fun, conceptual and useful assignments to take inspiration from as an art educator.
I got to thinking about the best assignments that I have received from my instructors over the years, and I've paired it down to three:
1) My high school art teacher gave us an assignment where we had to go out on the town over the weekend and find all the stores that might have useful (non-traditional) art supplies.
I lived in Hanoi, Vietnam at the time where I attended an international school and took the International Baccalaureate Visual Art 2-year course. This meant that not only did I have to document all of my findings in great detail for my teacher, but I first had to overcome the language barrier and navigate the bustling and winding streets of the old quarter on my mission. While at the time it was terrifying, it has become one of the most useful lessons I learned in high school because (a) I built the confidence to just go out and find stuff in an unfamiliar place, a skill that has served me well over the years, and (b) my idea of what art supplies should be and where you should get them was shaken and replaced with a more imaginative take on the whole thing.
2) One of my college professors, Craig Nagasawa, made me limit my palette to 6 colors plus white for a whole semester. The result was so successful that I didn't add any new colors until 2 semesters later. The purpose of this limitation was for me to stop being overwhelmed by the amazing array of color offered in oil paints today, and to really learn how to mix color and figure out how to make the colors that I needed. I now teach a class on color and whenever I see my students -- especially the color enthusiasts like myself -- come in with a box full of paints, I turn around and give them the same advice: limit your palette until you understand color better.
3) In my 2nd year as an art major, I took a class with Kara Maria, a visiting lecturer, and her assignment for the semester was: make ugly paintings. This seemed quite shocking to us fairly new painters/budding artistes, but her assertion was that in our naive pursuit of perfection our paintings became dull. By being given permission to make "bad" paintings, we were suddenly freed of our self-enforced restrictions and became bolder, more willing to experiment, and less afraid of "mistakes". My paintings definitely improved as a result of this simple idea, which I not only employ on my own students but I also have to remind myself of whenever I feel like my work is getting stuck.