Collins was born on January 14, 1911 in Reno, Nevada. As a child he hopped freight trains across the country and learned tattooing from a man named "Big Mike" from Palmer, Alaska. Practising on drifters, he later sailed the Pacific Ocean before settling in Hawaii. A big brute with a dirty mouth, he often wore plain white T-shirts that exposed his ink-sleeved arms. Mike Malone, who took over Sailor Jerry's shop after he died, described Jerry as "a class-A pirate".
At age 19 Collins enlisted in the United States Navy. During his subsequent travels at sea he was exposed to the art and imagery of Southeast Asia. He remained a sailor for his entire life thereafter. Even during his career as a tattoo artist he worked as a licensed skipper of a large three-masted schooner, on which he conducted tours of the Hawaiian islands.
At age 19 Collins enlisted in the United States Navy. During his subsequent travels at sea he was exposed to the art and imagery of Southeast Asia. He remained a sailor for his entire life thereafter. Even during his career as a tattoo artist he worked as a licensed skipper of a large three-masted schooner, on which he conducted tours of the Hawaiian islands.