Chesterton used to do a stand-up routine, called for purposes of advertisement a "debate," with his good friend George Bernard Shaw. They disagreed about practically everything. Shaw was a socialist, Chesterton a distributist, which Shaw thought amounted to being a socialist, but Chesterton didn't. From a 1928 debate:

Shaw: Now I have a very limited legal right to the use of [my] umbrella. I cannot do as I like with it. For instance, certain passages in Mr. Chesterton's speech tempted me to get up and smite him over the head with my umbrella.... But should I abuse my right to do what I like with my property--with my umbrella--in this way I should soon be made aware...that I cannot treat my umbrella as my own property in the way in which a landlord can treat his land. I want to destroy ownership in order that possession and enjoyment may be raised to the highest point in every section of the community. That, I think, is perfectly simple....

Chesterton: Among the bewildering welter of fallacies which Mr. Shaw has just given us, I prefer to deal first with the simplest. When Mr. Shaw refrains from hitting me over the head with his umbrella, the real reason--apart from his real kindness of heart, which makes him tolerant of the humblest of the creatures of God--is not because he does not own his umbrella, but because he does not own my head.

During an American tour in 1931, Chesterton debated Clarence Darrow in New York City. The topic was the Genesis story of creation. Darrow, one of America's leading freethinkers following his dismantling of William Jennings Bryant during the Scopes "Monkey Trial," did not fare well, according to the majority opinion of those who attended; they were asked to vote for the winner of the debate, and Chesterton won, 2,359 to 1,022. One attendee said that "the trained scientific mind, the clear thinking, the lightning quickness in getting a point and hurling back an answer, turned out to belong to Chesterton. I have never heard Mr. Darrow alone, but taken relatively, when that relativity is to Chesterton, he appears positively muddle-headed."

Chesterton's opening statement following Darrow's initial speech, was, "It may come as a surprise to you, Mr. Darrow, and perhaps to all of you in the audience, but I agree entirely with everything you have said." It threw Darrow into utter confusion. In referring to the event obliquely in his Autobiography, Chesterton mentioned that in America he had debated a man who seemed to be arguing with his fundamentalist maiden aunt.