Complex sentence: He was working as a freelance designer when he in 1953 was contacted by playboy founder Hugh Hefner who needed a logo for his new magazine, the now famous rabbit wearing a tuxedo bow tie.
Split into simpler sentences: He was working as a freelance designer when he in 1953 was contacted by playboy founder Hugh Hefner who needed a logo for his new magazine. He came up with the now famous rabbit wearing a tuxedo bow tie.