A pair of paintings from the famed series depicting dogs playing poker fetched nearly $600,000 at auction Tuesday.

The two works — "A Bold Bluff" and "Waterloo" — were among 16 paintings that artist Cassius Marcellus Coolidge (search) was commissioned to create for a Minnesota-based advertising company in 1903. Of the 16, nine are of dogs playing poker.

The two works that sold Tuesday for $590,400 capture moments in a poker game played by five dogs, among them a St. Bernard that ends up collecting the pot on a bluff.

The winning bid set a new auction record for Coolidge, whose previous top sale was $74,000, said Alan Fausel, director of paintings at Doyle New York (search), which handled Tuesday's sale.

The winning bidder was a private collector from New York.

Doyle had estimated that the two paintings would bring in between $30,000 and $50,000.

The sale was part of Doyle's annual "Dogs in Art" auction, which coincides with the Westminster Kennel Club (search) dog show.