As his career progressed, Cobb became well-known as an editor, reporter, columnist, and humorist in papers all over the state and nation. He hob-nobbed with the best of them through the years: politicians, actors and actresses, writers, and so on. But he never forgot his home state and seemingly retained a sense of morality. Early on (1900), he married Laura Spencer Baker - a marriage that lasted a lifetime.
Cobb was a larger-than-life figure. One of his early columns, as paraphrased here in the 1900 Earlington Bee, humorously commented on "Fads of Kentucky Statesmen." It included observations on Goebel, who would be assassinated only weeks later! Cobb went on to report in Europe in World War I. He saw the potential in film, and sold several scripts to Hollywood, not to mention appearing in a few or hosting the 1935 Academy Awards! But that was only the beginning.
Politics was not far from Cobb's thoughts. He vehemently wrote about and fought for what he believed in, including African-American rights and composing anti-Prohibition press releases.
In the first half of the twentieth century, Cobb was easily one of the most recognizable (and quotable!) American celebrities directly connected to Kentucky. He died on March 10, 1944, and now rests in Paducah, quite appropriately under a tombstone reading "Back Home."