In The New Yorker Cartoon Caption Contest #1004 from the issue of September 7, 2026, a woman carries drinks to a seated man while her dog brings him a chessboard set up for play. The woman speaks. My submission is shown below. The drawing is by Mort Gerberg.
"I should warn you he doesn't like sore losers."
These captions weren't grandmaster moves:
"He plays for $100 a game. Here, have a drink." "Oh, no. He just likes to fetch the pieces."
September 19, 2026 Update: The Finalists
September 27, 2026 Update: I voted for the caption from Tokyo.
In an original New Yorker cartoon from the summer of 1978, Donald Reilly's boater muses on how "Life can be good . . ."
"Life can be good, I've found. It all depends on the product, the media mix, and the demographics." Donald Reilly Framed original art The New Yorker, August 21, 1978, p. 27
The eBay seller may have misspelled the name of this piece's original owner. It seems to have come from the collection of American expressionist painter Harry Shoulberg (1903-1995).
Donald Reily eBay item description
[End of eBay listing]
"Life can be good, I've found. It all depends on the product, the media mix, and the demographics." Donald Reilly The New Yorker, August 21, 1978, p. 27
"Life can be good, I've found. It all depends on theproduct, the media mix, and the demographics." Donald Reilly Framed original art The New Yorker, August 21, 1978, p. 27
As the commercial airline industry boomed in the postwar period, affluent Americans did more traveling abroad, particularly in Europe. The New Yorker went with them. Charles Saxon's 1966 magazine cover depicts two older couples taking a gondola ride in Venice, a gentle subversion of our romantic expectations.
Charles Saxon Original art The New Yorker, June 25, 1966
The original cover art is on display at "Drawn From The New Yorker: A Centennial Celebration" at the Society of Illustrators. The exhibition, curated by Liza Donnelly, also includes a print of a classic Saxon cartoon from the mid-seventies. No one captured the upper classes and their attitudes quite like Saxon.
"It was nice. Hard times give everyone such a sense of camaraderie." Charles Saxon Print The New Yorker, April 7, 1975, p. 33
"It was nice. Hard times give everyone such a sense of camaraderie." Charles Saxon The New Yorker, April 7, 1975, p. 33
With a chess spot by TG and a cartoon by Charles Saxon
There's another lot in Doyle's recent Stephen Sondheim sale that caught my attention. It contained eight caricatures from the composer's estate. The songwriter kept many framed likenesses of himself. Some are original art and some are reproductions.
Martin Kreloff
Naturally one of the original works caught my eye right away, an original mock-New Yorker cover.The unsigned caricature here is, alas, not a good likeness. The rhyming dictionary may well have been one of Sondheim's tools, but he could hardly have relied on it enough to merit its inclusion front and center. This seems to detract from his accomplishment, which countless other musical composers with countless other rhyming dictionaries could hardly approach. The chess board on which the master writes music has gotten the dark and light squares all wrong, the graphic equivalent of a lyric that doesn't quite scan. I suppose this was something made as a personal gift and never actually submitted to the magazine, but anything's possible. The presence of the frame, at least, suggests That Sondheim himself was pleased with it, as he must have been pleased with all these pieces.
Trog (Wally Fawkes)
John Minnion
The lyrics in the Squigs picture are from "Anyone Can Whistle," "A Little Night Music," "Company," "Sweeney Todd," "Marry Me a Little", "Into the Woods," and "Sunday in the Park with George." There may be other shows represented as well.
In the CartoonStock Caption Contest #177, the white knight is on the witness stand as the trial is played out on a chess board. The rules of the monthly cash prize contest have not changed and neither has my description of them: five dollars buys up to three entries. Real cash prizes are $500 for first place and $100 for each of five runners up. As of this writing, I've put $110 into the first twenty-two pay-to-play contests and this twenty-third challenge brings my total cash outlay up to $115. Having had two previous runner-up entries, I've collected $200, so I'm still playing with the house's money, thank goodness. In fact, so few contestants enter that the odds are generally favorable even to us less-gifted caption writers—and chess players. My three entries are shown below, above the break. The cartoonist is Bob Eckstein.
"Did you or did you not take the black queen for all she was worth?" "What kind of pervert forks the queen and the king?" "How can you claim to begin on a white square and yet end up on black?" * * * "The witness will refrain from jumping . . . to conclusions." "And what heinous action did you take when the Queen's Gambit was declined?"
This week, I contemplated my move in The New Yorker Cartoon Caption Contest #801 from the issue of May 9, 2022. My entry is shown below. The drawing is by Adam Sacks.
"That settles it. We just go to Hell's kitchen."
May 21, 2022 Update: The Finalists
May 28, 2022 Update: I voted for the caption from South Burlington.
Barney Tobey's drawing of two men playing chess was originally sold by the Nicholls Gallery in New York to a collector in Lansing. It may or may not have been included in his 1976 exhibition there. It is apparently an illustration or spot drawing but its publication history is uncertain. It was offered on eBay in August at $599, then the price was raised $1,000. It was sold in September for an undisclosed best offer price.
There is liberal use of white out.
Barney Tobey's signature
Based on the pencil lines, Tobey relocated his signature slightly to the right.
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