Theodore Roosevelt was a man’s man — the very image of individualism, strength, and courage. It is hard to imagine anyone making fun of the man who would become the 26th President of the United States.

There was a period of time, however, when Roosevelt less resembled the Rough Rider of legend and looked a lot more like an out-of-place city slicker on horseback. Shortly after the death of his first wife, Roosevelt went to the Dakota Territory to work as a rancher and develop some skills in the Wild West. Although he dressed the part of a cowboy quite well, the moment he opened his mouth it was clear that he had a lot to learn. His fellow cowboys were openly amused when Roosevelt urged his horse forward, and instead of saying, “Giddyup,” he would command, “Hasten forward quickly there!”