Robert "Rupe" Baldwin attended courses at the Corcoran Art School of Washington. His main focus was to become a painter, but financial reasons drove him to humorous illustration and eventually comics. After several works for comic books, he took on the newspaper strip 'Freddy'. This strip appeared from 1955 to 1980 and was syndicated by the Washington Star Syndicate and later Field Enterprises. Baldwin was assisted by Howard Rands in the 1960s, and some of the writings were done by his wife, Helen.