What might be taken at a first glance for Alf Bergan’s improvised joke about Dennis Breen turns out to be a fairly standard expression hinting at some physical or mental defect. The expression has in fact survived into the 21st century as a T-shirt slogan quoting Muhammad Ali: "I'll beat him so bad he'll need a shoehorn to put his hat on."1
Its origins go back at least to the middle of the 19th century:
A CRITERION FOR A DRUNKARD. On Saturday evening last a countryman visited Burnley, and was complaining of the trouble a drunken man had given him. "How do you know he was drunk?" said a bystander. The countryman indignantly replied, "What could he be else, when he asked for the shoehorn to put his hat on with?"
Blackburn Standard (1851), 5 November
The expression invariably refers to either of two groups of swollen heads: those with their heads swollen by drink or stupidity, and those of people physically threatened by or suffering from violence to the head:
"Here, Solomon," says Levi, "I want to make you a prisent."
"An' what's this?" Asks Solomon, examining the article that has been handed to him.
"A shoe horn."
"An' what do I want wid an ould shoe horn?"
"Thry an' get your hat on your head with it" answers Levi, amid an outburst of merriment from the audience.
"A team of Irish comedians", in John Joseph Jennings, Theatrical and Circus Life (1882), p. 428
As George Bergman of Berkeley has pointed out in private correspondence, a large or swollen head (and megalomania) often seems at the time to correlate with insanity, and the following generation regarded a psychiatrist as a "head-shrinker" or a "shrink". Alf's invitation to the cronies in Barney Kiernan's bar ("Look at his head") confirms this popular myth.
How's your old head this A.M.? said Oppenheimer, in his slangy way: "I had to put my hat on with a shoehorn. I looked in on the boys in Pete Cannon's last night, just for ten minutes, and the interest was prolonged. Oh, I got elegant — nickel-plated. Pete took me home himself..."
Puck (1882), vol. 10 p. 416
Then he chucks his hat down on the ground and begun dancin' and cussin', and wants to fight me. 'Keep cool, my lad' — I says, 'and put your hat on while it fits you. In ten minutes you might want a shoe-horn to put it on with'…
Francis Wylde Carew, No. 747: Being the Autobiography of a Gipsy (1881), p. 112
A late nineteenth-century children’s poem similarly hints that the expression could also indicate the behaviour of a lunatic:
The Contrary Man.
A contrary mortal was Anthony Slaughter –
He washed in the towel, and wiped in the water,
And put both his legs through his shirt to get in it,
And forced off the buttons on purpose to pin it.
He put on his hat with a shoehorn discreetly,
Employing a bootjack to take it off neatly;
Hampshire Telegraph and Sussex Chronicle (1898), 3 September
When Molly Bloom thinks of Dennis Breen she remembers being told “that sometimes he used to go to bed with his muddy boots on when the maggot takes him” (U 18.222-3). It may be more than a coincidence that both signs of drunkenness (or madness in Breen’s case), the shoehorn to put on one’s hat and the boots in bed turn up combined in this nostalgic memory of better times:
For in those days chippiness was never known, and a shaky hand undreamt of; the matutinal brandy and soda was never wanted, and the going to bed in one’s boots never entailed putting on one’s hat with the shoehorn the next day.
Sporting Times (1884), 25 October p. 3