Old West heroine the Black Phantom in Magazine Enterprises' Western comic Tim Holt #25 (Sept. 1951). Through 1954, he also drew the title feature as well as the backup feature "Redmask", then took over the art for the spinoff series Red Mask, drawing issues #42–53 to (July 1954 – May 1956). Additionally, for DC Comics, Bolle drew the cyborg-superhero feature "Robotman" in Detective Comics #167–179 (Jan. 1951 – Jan. 1952). From 1955 to 1957, Bolle drew Robin Hood stories in ME's Robin Hood and the subsequent, TV series-based The Adventures of Robin Hood. For Marvel Comics' 1950s forerunner, Atlas Comics, he drew supernatural fantasy stories in the anthologies Mystic, Marvel Tales, Strange Tales, Journey into Mystery and other titles in 1956 and 1957. As well by the mid-1950s, Bolle was illustrating juvenile fiction books, including Gene Autry & Champion (1956), and books starring Lassie and the Lone Ranger. He would later draw for the Choose Your Own Adventure children's book series. From 1957 to 1961, Bolle began his long career in newspaper comic strips, starting as an art assistant, drawing backgrounds, on the Chicago Tribune-New York News Syndicate's daily and Sunday On Stage from 1957 to 1961. 1960s This briefly overlapped his own Sunday comic strip, the McNaught Syndicate's Children's Tales, which he wrote and drew from 1960 to 1969. He recalled it as "a Sunday page where I illustrated some classics like 'Cinderella' and 'Rumplestilskin' and I did them in three parts so they would appear on three Sundays. And in-between that I would also write original stories, so I wrote about 12 to 15 original stories, then I would switch back and forth from classics to originals." For the same syndicate, he drew the daily and Sunday strip Debbie Deere, "a lonely hearts writer [who] would get involved in some of the letters she got. I did that for about 4 years," from 1966 to 1969. For the Chicago Tribune-New York News Syndicate, he wrote and drew the strip Quick Quiz from 1964 to 1965. By this time he was also illustrating for magazines, beginning with the men's adventure title Stag from 1961 to 1962. He used the pseudonym F. L. Blake for the dust jacket of the 1963 book Picture Parade of Jewish History. Keeping a hand in comic books, Bolle drew the superhero series Doctor Solar, Man of the Atom #6–19 (Nov. 1963 – April 1967)