Bob Gregory attended the Otis Art Institute and fought in World War II before working as a technical illustrator for an aircraft manufacturer.
He began submitting art sketches to Western Publishing, for which he began freelancing on a steady basis in 1958 — first as a writer, then as a writer-artist both writer and artist — on many of Western's talking animal comics, including the Donald Duck comics produced under license by Dell and Western's Gold Key Comics.
Gregory produced hundreds of Disney comics stories for many publications, including Donald Duck, Daisy Duck's Diary, Junior Woodchucks, Uncle Scrooge, Walt Disney's Comics and Stories, Walt Disney's Christmas Parade, and Brazil's Zé Carioca.
[3] He introduced the Billionaires Club of Duckburg, where Scrooge McDuck is a member, in the story The Christmas Cha Cha (Dell Giant #26, Nov 1959), written by Gregory and illustrated by Carl Barks.
His World War II memoirs, Letters from the South Pacific, was published in 1996.