Did you know that Dogs Playing Poker was a series? I didn't. In fact, the painter, Cassius Coolidge painted eighteen different paintings of dogs playing poker. The first painting, "Poker Game", released in 1894, was sold in 2015 for $658,000.

Background
Coolidge was born in Antwerp, New York, and was raised in Philadelphia, New York. He lived on a farm in his early life and left the family farm in the 1860s. He had several careers between 1868 and 1872. For instance, he worked as a druggist, an older way of saying that he was a pharmacist.

Coolidge also owned a bank, the Bank of Antwerp, which was established in 1872, but ownership was transferred to John D. Ellis in 1874.

In addition, he worked as a Cartoonist, Sign Painter, and then moved to Rochester, New York. He began his art career in his twenties, and is credited for inventing "Comic Foregrounds". You know those painted wooden scenes that you can stick your head through at Theme Parks? You have Mr. Coolidge to thank for those.

Dogs Playing Poker
Coolidge painted the first Dogs Playing Poker painting in 1894. Sixteen more were commissioned by a company called Brown & Bigelow. Brown & Bigelow is a publishing company based in Saint Paul, Minnesota. It's known for selling branded and promotional merchandise, and in Coolidge's case, hiring artists for advertisements.
Yes, sixteen of the dog-themed paintings were commissioned for the purpose of selling... cigars. Yup, cigars. Brown & Bigelow printed out hundreds of thousands of copies of the paintings, sold in advertising posters, calendars, and prints.

In addition to "Poker Game", his paintings were titled "A Bachelor's Dog", "A Bold Bluff", "Breach of Promise Suit", "A Friend in Need", "His Station and Four Aces", "New Year's Eve in Dogville", "One to Tie Two to Win", "Pinched with Four Aces", "Poker Sympathy", "Post Mortem" , "The Reunion", "Riding the Goat" ,"Sitting up with a Sick Friend", "Stranger in Camp", "Ten Miles to a Garage", and "A Waterloo". In 1910, Coolidge produced an additional painting, called "Looks like Four of a Kind".
Not all of the paintings were about Poker, however. In fact, only "A Bold Bluff", "A Friend in Need", "His Station and Four Aces", "Pinched with Four Aces", "Poker Sympathy", "Post Mortem", "Sitting Up with a Sick Friend", and "A Waterloo" (8 out of 16) are poker related.

"A Bachelor's Dog" shows a dog reading the mail, "Breach of Promise Suit" shows a dog testifying in court, and "Riding a Goat" is about… exactly what the title says it is about.

C. M. Coolidge's Legacy
Coolidge's paintings have remained iconic and popular to this day. They have been attached to various pop-mediums, even in Coolidge's own time. Nowadays, you can find his paintings anywhere from movies ("The Thomas Crown Affair"), to TV shows ("Roseanne"), to cartoons ("The Simpsons"), to parody illustrations ("Dogs Playing Dungeons and Dragons"), and even to online casino sites and video games.

On February 15th, 2005, "A Bold Bluff" and "A Waterloo" were auctioned as a pair to a buyer in the United States, for $590,000. This sale beat out the previous highest sale for a Coolidge painting ($74,000), but the top spot was taken in 2015, when "Poker Game" sold for $658,000, and remains to the date of writing, the highest price paid for a Coolidge painting.

In 2018, the sponsors of the World Series of Poker, commissioned a "Modern Reimagination" of the classic paintings. Notably, it is a picture taken of real dogs posed around a Poker Table, rather than a painting. In it, a Jackapoo, a Rottweiler, a Staffordshire Bull Terrier, and a Golden Retriever sit around a table playing Texas Hold'Em.