Like many artists, Ripley did a lot of drawing from a very young age. His first published cartoon/illustration was in a 1908 issue of Life when he was 17 years old, for which he was paid eight dollars. In early 1909, he moved to San Francisco and, thanks to a family friend, began working for The Bulletin as a sports cartoonist. He wasn't particularly successful and encountered a number of difficulties in San Francisco, so in 1912 he moved to New York where he thought his prospects as a cartoonist would be better.
After trying out unsuccessfully for the New York Giants (yes, the baseball team!) he began working as a sports cartoonist for The Globe with his first cartoon published in early 1913. His sports cartoons were well-received enough, but not especially note-worthy. Given that era's limitations in mitigating weather, things always slowed down considerably during the winter months and he would often have difficulty find topics to cover in his cartoons. After several years of this, in 1919 while facing his next deadline, he threw together a collection of odd sports facts from clippings he had collected over the years. Entitled Champs and Chumps (seen in the photo here) it's generally seen as the first attempt at the type of thing that would later make him famous (often cited as such by Ripley himself).
However, it would be another ten months before another similar installment would be published; this time, he actually began calling it Believe It or Not. Though his Believe It or Not feature did start seeing more frequency, it still only appeared once every two or three months. (Again, generally because Ripley was facing a deadline and strapped for ideas.) He also began adding text pieces to accompany his cartoons and the paper began touting his work as one of their selling points.
The paper found him to be such a valuable artist and storyteller that in 1922, they sent him on a fully paid, four month trip around the world with their only real stipulation being that he was to chronicle what he saw and experienced. He filed a Ramble 'Round the World with Ripley column nearly every day, each with an illustration of some strange new sight. Given the restrictions of travel, much of what he saw was entirely new to him (one of his cartoons is captioned simply "We see our first Hindu") and because most of his readers shared his previous limited travel experience, his pieces became very popular.
When he returned to New York, Ripley began infusing his Believe It or Not cartoons with items beyond sports. Obviously influenced by his travels. This caught the attention of Dick Simon and Max Schuster, then publishers of crossword puzzles, but Ripley turned down their book offer, feeling he was better suited to newspapers.
Ripley's cartoons caught national attention when, in 1927, he included a blurb noting that Charles Lindbergh was in fact the 67th person to fly across the Atlantic Ocean. Given how much celebrity Lindbergh had himself garnered via his flight, Ripley drew a great deal of ire from readers, claiming he was anti-American. He let the furor build before offering that the observation that he never claimed Lindbergh wasn't the first person to make a solo flight, and that there were in fact a three previous trans-Atlantic crossings each featuring multiple people. That wound up being a very successful tactic for him, and he began using more facts that seemed to upend conventional knowledge. So when he finally did agree to Simon and Schuster's book deal, the collection of his cartoons went flying off the shelves, becoming an instant best-seller!
The book landed in front of newspaper publishing mogul William Randolph Hearst in 1929, who then began syndicating Ripley's Believe It or Not worldwide. Ripley's contract was for $100,000 year (about $1.5 million today). The following year, he began to be featured in Vitaphone shorts and in radio programs shortly after that. In 1933, he opened his first "odditorium." By the mid-1930s, his income had climbed to a half million a year (about $900,000 today).
Despite his work in other media, Ripley continued drawing the strip until his death in 1949. He did have a variety of assistants and ghost artists, however, throughout much of his tenure, with Paul Frehm taking on the full art chores after Ripley's death. Paul's brother William began helping, too, in 1948 and took over full-time in 1978.
Despite being known as a curator of the strange and unusual, Ripley spent most of his career as a newspaper cartoonist, and he only spent 20 of his 58 years as the popular collector of the odd.
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