Norman Pettingill began making art as a boy, but came into his own as an artist as a young man in the 1920’s. His first job as a commercial artist began in 1925 at the age of twenty-nine. The art of Norman Pettingill came to the attention of the John Michael Kohler Arts Center in Sheboygan, Wisconsin, in 1983 through artist Ken Little, who had shown a set of Pettingill’s prints to Arts Center Director Ruth DeYoung Kohler.
Working directly with Pettingill, age 88 at the time, the Arts Center mounted the first museum exhibition of Pettingill's work, titled Norman Pettingill: Northwoods Humorist. Drawings in the exhibition ranged from 1937 to 1974. Pettingill regularly used local hunters, anglers, and tavern habitués as his subject matter, along with any number of Northwoods creatures: moose, bears, deer, and fish. In 1993, the Arts Center worked with the Kohler Foundation to acquire the primary body of Pettingill’s work – some one hundred and eleven original drawings.
Additional pieces were added in 2008, when Kohler Foundation acquired the collection of Buz Holland, who was a serious collector of Pettingill's work.