Dudley was raised in Columbus, Montana. He received a PhD in clinical psychology from the University of Montana. Simultaneously, he studied and was an assistant to Professor Dick Reinholtz in the UM art department.  Dudley and his wife, writer and psychotherapist, Candace Crosby opened the Dana Gallery in 1996. Dudley has had major shows with the Hockaday Museum, the Holter Museum of Art, the Museum of Art and Culture at University of Montana.

He was selected as one of the 63artists, and the only photographer included in the Out West Meridian International Center in Washington DC for a major exhibition that toured all the major art museums of China. Dana has donated a number of art pieces to the Missoula Art Museum Annual Auction since 1994. He has served as resident artist in Glacier National Park, Providence Seashores National Monument, and the prestigious Ucross Foundation.

Dudley’s work is divided into three main bodies which include landscape, digital paintings and over 100 mixed media works that incorporate his photographs of Montana Roads, favorite song lyrics and his own writing and poetry. His pieces have been collected by David Boiese and Ted Stevens, the two opposing attorneys who argued each side in the 2000 Gore and Bush election decided by the Supreme Court.

The Dana Gallery has been named Best Gallery in Missoula for 18 years and in 2018 was named one of the Top 25 Galleries in America as well as the Best Gallery in Montana.