I did love the process of making characters very loose with big pen with my right hand (I'm left handed). It was so fun...
This cowboy I did in a play session and I think it's one of the best drawing I've ever done in my life. There's so much character in it.
-Put a sheet of paper on the table.
-Two people are suppose to draw on this sheet.
-In the middle of the sheet block your partner's view so he can't see what you're drawing and vice-versa. (I did that by holding another sheet of paper in between us)
-Draw an "open shape" figure (one that doesn't close on itself like a circle or a square) with the open space facing the half of the paper you're not seeing.
-When you and your partner finish a simple opened shape, take the "wall" between the drawings and try to match the shapes in order to have something figurative.
As you can see the hat and the body have different styles. That was where we devided the paper. I drew the square shape and a friend drew the round hat. When the shape was finishe I spoted a potential cowboy so I added the limbs and the face.
(Ok, due to the round shape that became a hat I have to say that this was a colective drawing, not exclusive mine :)