Cassius Marcellus Coolidge, an American jack of all trades then in his late fifties, painted the dogs. In 1903 the St. Paul advertising firm Brown and Bigelow hired him to paint sixteen scenes of dogs behaving like men, to sell cigars on calendars and cigar boxes. The most famous, A Friend in Need, shows a bulldog passing an ace under the table.
Brown and Bigelow specialized in what the trade called remembrance advertising, a calendar or a print meant to stay on someone's wall long after the sales call was forgotten. The dogs were its way of selling cigars.
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But Brown and Bigelow did not invent the dogs. Nine years earlier, in 1894, Coolidge had already painted dogs around a card table and called the canvas Poker Game. When the St. Paul firm hired him in 1903, it was paying for an idea he already had, and asking him to come back to it in a series of sixteen.
That first painting is the one the market remembers. In November 2015 it sold at Sotheby's in New York for 658,000 dollars, a record for Coolidge. It beat the mark set ten years earlier by two of the cigar paintings.
So the most expensive Coolidge ever sold is not one of the sixteen. I read that as a sign that the dogs were his own joke before they were an advertiser's.
Who was Cassius Coolidge before the dogs?
Coolidge was born in 1844 in Antwerp, New York, and spent his first decades changing jobs. He painted signs, worked as a druggist, drew cartoons for a local newspaper, and founded a bank and a newspaper of his own. His family called him Cash.
Through all of it he had a gift for the visual gag. In April 1874 he was granted a patent for a way of photographing a person's head, enlarged, on a small drawn body held up in front of the sitter, and he is credited with inventing the comic foreground, the painted board with a hole where a tourist puts a face.
In 1903 a St. Paul advertising firm gave him the job that made his name: sixteen oil paintings to sell cigars.
What You'll Discover
Why a cigar firm wanted dogs.
What the bulldogs are up to.
What a pair of them fetched.
What a film hid behind one.

