Atheist/Christian. Aquabib/wine drinker. Thin/fat. Vegetarian/meat eater. Socialist/Distributist.
Shaw/Chesterton. They fought it out in print, they fought it out verbally.
It would've been great to see those debates. But what made them so good? Chesterton's early biographer, Maisie Ward, explains it better than anyone. She starts by pointing out that Shaw was asking the questions that infuriated the British conventional class, but so did Chesterton:
They hated Shaw's questions before they began to hate his answers. And that is probably why so many linked Chesterton with Shaw -- he gave different answers, but he was asking man of the same questions. He questioned everything as Shaw did -- only he pushed his questions further: they were deeper and more searching. Shaw would not accept the old Scriptural orthodoxy; G.K. refused to accept the new Agnostic orthodoxy; neither man would accept he orthodoxy of the scientists . . .
They attacked first by the mere process of asking questions; and the world thus questioned grew uneasy and seemed to care curiously little for the fact that the two questioners were answering their old questions in an opposite fashion. Where Shaw said: 'Give up pretending you believe in God, for you don't,' Chesterton said: 'Rediscover the reasons for believing or else our race is lost.' Where Shaw said: 'Abolish private property which has produced this ghastly poverty,' Chesterton said: 'Abolish ghastly poverty by restoring property.'
And the audience said: 'These two men in strange paradoxes seem to us to be saying the same thing, if indeed they are saying anything at all.' . . .
Shaw and Chesterton were themselves deeply concerned about the answers. Both sincere, both dealing with realities, they were prepared to accept each other's sincerity and to fight the matter out, if need were, endlessly.
For perhaps the best essay on the web about Chesterton and Shaw, check out Fr. Ian Boyd's CHESTERTON-SHAW DEBATE SPEAKS TO THE PRESENT CRISIS. Fr. Boyd is one of the world's foremost Chesterton authorities and has done much to trigger the Chesterton renaissance.
GKC on GBS (from The Quotable Chesterton):
"Mr. Bernard Shaw's philosophy is exactly like black coffee--it awakens but it does not really inspire."
"He has pleased all the Bohemians by saying that women are the equal to men; but he has infuriated them by suggesting that men are equal to women."
"The truth is, of course, that Mr. Shaw is cruelly hampered by the fact that he cannot tell any lie unless he thinks it is the truth."
A few Shavian anecdotes (from The Little, Brown Book of Anecdotes):
Before Shaw became famous, one of his plays was consistently turned down by a certain producer. After Shaw achieved success, the producer cabled an offer to stage the rejected work. Shaw replied, "Better never than late."
A dancer approached Shaw, suggesting they should have a child together. "Think of it! With my body and your brains, what a wonder it would be," she said. Shaw replied, "Yes, but what if it had my body and your brains?"
Saddled with a pompous young bore who barraged him with pointless information during a dinner party, Shaw said, "You know, between the two of us we know all there is to know." The young man eagerly asked, "How is that?" Shaw replied, "Well, you seem to know everything except that you're a bore. And I know that."
The Socialist Shaw liked money. When a young anthologist wrote to Shaw, asking to include one of Shaw's pieces in an anthology but explaining that he couldn't pay much because he was a very young man, Shaw replied, "I'll wait for you to grow up."
Shaw loved flowers. When Arnold Bennett visited Shaw's apartment, he was surprised to see there were no flowers in the place. He said to Shaw, "I thought you so fond of flowers." Shaw said, "I am, and I'm very fond of children too, but I don't chop their heads off and stand them in pots about the house."