Caption Contest Commentary

In my fellow Chicagoan Pat Byrnes’ drawing, two mobsters have fitted their latest victim with concrete shoes and thrown him off a pier and into the river. His head, however, remains above water because he’s landed safely on top of a pile of other victims. He’s saying something to the mobsters on the pier. My…
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In J.B. Handlesman’s cartoon, a bartender is addressing Ulysses S. Grant, whose face appears on a huge $50 bill. Ron Chernow, who wrote the Alexander Hamilton biography that Lin-Manuel Miranda turned into a smash Broadway musical, recently wrote a biography of Ulysses Grant, so I initially imagined the bartender speculating about Grant’s chances of becoming…
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Charles Barsotti has drawn a robber on a therapist’s couch. Next to him is a huge bag of stolen money, and the therapist is sitting in a chair. The robber/patient is talking happily. There’s always a temptation when captioning a Barsotti cartoon to reference his classic drawing of a piece of pasta saying into the…
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In Kim Warp’s drawing, a cowboy on a horse is consulting a book and addressing a fallen cowboy he’s lassoed around the ankles. I first thought about the trope—common in old westerns—of dragging a cowboy behind a horse. In Warp’s drawing, of course, the lassoed cowboy is in front of the horse. Maybe, then, the…
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Robert Leighton has drawn a scene from an elementary school play. A teacher/director is backstage addressing two students who are dressed as an apple and a banana. Another student, dressed as a slice of bread, is on stage performing for the audience. I initially assumed the teacher was trying to answer the traditional actor’s question…
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In the late J.B. Handlesman’s cartoon, a judge is presiding over a jury trial where the attorneys for both parties have fallen asleep (or passed out) at their tables. The jurors, the witness, and the judge are all looking at these two unconscious advocates, and the judge is speaking. When an attorney finishes presenting his…
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