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"He is something of a pagan," said Chesterton of George Bernard Shaw, "and like many other pagans, he is a very fine man." The assessment hints at the complexity of their relationship.

The prolific playwright, critic, essayist, and Irishman G.B. Shaw first met Chesterton in 1901. They disagreed about nearly everything, but they remained friends for a tumultuous yet playful 35 years.

Of Shaw's more than 50 plays, American audiences are most familiar with Pygmalion, on which the musical My Fair Lady is based. The themes in that story—class division, the power to remake oneself—barely hint at the author's deeper, and to Chesterton's mind more dangerous, ideas about the world.

To frame their differences simply, Shaw believed in man, or Nietzsche's Superman, while Chesterton believed in the Son of Man. Shaw, a socialist, looked for society to develop the values of humanism and thereby help a superhuman "life-force" become a god. Chesterton, who believed that all life owed its existence to God, called society back to Christian humility.

Chesterton debunked Shaw's theories on many occasions, always with humorous grace. In 1905, Chesterton gave Shaw his own chapter in Heretics. In Orthodoxy, published in 1908, Chesterton writes, "I know of men who believe in themselves more colossally than Napoleon and Caesar. I know where flames the fixed star of certainty and success. I can guide you to the thrones of the Supermen. The men who really believe in themselves are all in lunatic asylums."

Shaw could dish out challenges, too. In a 1908 letter he told Chesterton to write plays rather than newspaper columns, threatening to "destroy" his credit "until starvation and shame drive you to serious dramatic parturition."

Instead of a play, Chesterton gave the public George Bernard Shaw (1909), a biography with the preface: "It is indefensibly foolish to attempt to explain a man whose whole object through life has been to explain himself."

Chesterton and Shaw began a series of public debates in 1911 that continued until 1928. Their last public debate received the apt and ironic billing "Do We Agree?" Chesterton claimed that it would take his friend 300 years to agree with his views, if he could live that long, but he would "certainly" agree.

Despite their creative goading, Chesterton, in his Autobiography, completed just weeks before his death, wrote movingly of their relationship: "I have argued with him on almost every subject in the world, and we have always been on opposite sides, without affectation or animosity. … It is necessary to disagree with him as much as I do, in order to admire him as I do; and I am proud of him as a foe even more than as a friend."

—Zachry O. Kincaid

"Mr. Kipling does certainly know the world," Chesterton wrote; "he is a man of the world, with all the narrowness that belongs to those imprisoned in that planet."

An international celebrity in Chesterton's day, Kipling was a renowned storyteller and poet. His tale of a young boy named Mowgli, in The Jungle Book, remains a classic. But Kipling's internationalism, Chesterton believed, inevitably led to a program of "making the world smaller"—robbing the world of its wonder by conquering it. And Kipling did love conquest.

Born in Bombay in 1865, Kipling began his writing career as a teenage reporter for Anglo-Indian newspapers. On the side, he began to write the short stories and poetry that would eventually win him fame—and the Nobel Prize for Literature, in 1907. He always heartily supported British imperialism.

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