Watterson was awarded the Reuben Award for "Outstanding Cartoonist of the Year" from the National Cartoonists Society in 1986, the youngest person to win the award. In 1988 he won this award again, and was nominated in 1992.
Watterson spent a huge portion of his career trying to change the climate of comics. He believed that the artistic value of comics was being undermined, and that the space they occupied in newspapers continually decreased and was subject to arbitrary whims of publishers. Watterson believed that art should not be judged by the medium for which it is created (i.e., that there is no "high" art or "low" art, just art).
Watterson is also known for battling against the arbitrary structure imposed on newspaper cartoons by the publishers: the standard cartoon starts with a large wide rectangle featuring the cartoon's logo, and the strip is presented in a series of rectangles of different widths, limiting the cartoonist's options of allowable presentation. Watterson managed to get an exception to this constraint for Calvin and Hobbes, allowing him to draw his Sunday cartoons the way he wanted. In many of them the panels overlap or contain their own panels; in some of them the action takes place diagonally across the strip.
Moreover, Watterson battled constantly against the many things that he felt cheapened his comic. He felt that pasting Calvin and Hobbes images on commercially-sold coffee mugs, stickers and t-shirts devalued the characters and their personalities. This might also explain his refusal to allow the strip to become an animated series. Watterson fought this uphill battle against the pressure from publishers until the end of his career.
Since retiring in 1996 Bill Watterson has taken up painting.
Two speeches by Bill Watterson are available at several locations on the Web: