Born and raised to an impoverished Lithuanian Jewish immigrant family in Chicago, Friedman began riding the rails as a hobo during the Great Depression, and first arrived in Oregon as a hitchhiker in 1933.
While working on and off in canneries and as a merchant seaman, he took courses at six different colleges and universities.
He led a travel class called "Oregon for the Curious" for Portland Community College (PCC), and also taught writing and folklore at PCC and at Portland State University.
Friedman's highway guides, such as Oregon for the Curious (1966) catalogue obscure, off-the-beaten-path parts of the state and are often illustrated with historical anecdotes, spurts of creative purple prose, and criticism of commercial overdevelopment and environmental degradation.
Regional writer Matt Love believes that they may have helped inspire the environmentalist reforms promulgated during Tom McCall's gubernatorial administration.