This article from History.com tells a little of his history as an entertainer, and I think you'll find it interesting.
Nov 4, 1879:
Will Rogers is born in Oklahoma
On this day, the cowboy philosopher and humorist Will Rogers, one of the most beloved entertainers of the early 20th century, is born on a ranch in Cherokee Indian territory.
The son of a respected mixed-blood Cherokee couple, William Penn Adair Rogers grew up riding and roping on the plains of Oklahoma. An indifferent student, he earned only average grades in school, but he was by no means the ill-educated common man that he later liked to pretend. He was, in fact, highly literate and well read. In 1898, he left his family ranch to work as a Texas cowboy, and then traveled to Argentina where he spent a few months as a gaucho. But Rogers discovered his real talent when he joined Texas Jack's Wild West show in 1902 as a trick roper and rider under the stage name "The Cherokee Kid." For all his skill with ropes and horses, Rogers soon realized that audiences most enjoyed his impromptu jokes and witty remarks. Eventually, Rogers began to focus on making humorous comments on world events and created a popular vaudeville act with which he traveled the country.
In 1919, Rogers' first book, The Peace Conference, was published. In the 1920s, he achieved national fame with a series of movie appearances, radio shows, lecture tours, magazine articles, and regular newspapers columns. Amazingly prolific, Rogers eventually wrote seven books, an autobiography, almost 3,000 short commentaries called "daily telegrams," more than 1,000 newspaper articles, and 58 magazine articles. Rogers' warm, folksy manner and penetrating wit were hugely popular during the Depression, and his concern for the welfare of average folks was genuine. He contributed frequent charitable performances in support of the victims of floods, hurricanes, and earthquakes worldwide.
On August 15, 1935, Rogers was on a flight to Asia with the famous pilot Wiley Post when the craft developed engine troubles and crashed near Point Barrow, Alaska. The crash killed both men. Rogers was only 55.
Funny how you sometimes find out things about someone that proves they were more than they seemed to be. Such was the case with Will Rogers. A true American entertainer worth a great deal of respect!
Coffee out on the patio today, if that's OK with ya'll.