My favorite videos to show are the "Getting to Know the World's Great Artist" series from Mike Venezia. They are educational, funny, and keep my students engaged through the entire program.
My personal favorite is "Getting to Know Andy Warhol." I usually save it for the end of the year when I have a mixed up crazy schedule.
The video is about 20 minutes long and leaves plenty of time for discussion. I show photos of Warhol's soup can paintings and we use Visual Thinking Strategies to analyze the work. This year I showed the video in first grade. After we looked at and discussed the paintings, I taught students how to draw a cylinder. They practiced several times on a sketch page. Next, we talked about the brand of soup (Campbell's) versus the flavor of the soup (tomato). I asked students to come up with creative brands and flavors for their own cans. I thought this worked well with the 21st century skill of creativity and critical thinking. It also fits in with Common Core and ELA standards!
Finally, when students had a finished idea, we drew our best can on a large paper, wrote our brands and flavors, added any illustrations, traced and colored.