Here's the first item I've turned up. From May 20, 1906, it's Lyonel Feininger's THE KIN-DER-KIDS (ABROAD). Seems to be about a group of schoolboys being pursued by their old aunt. The more I look, the more odd little gags I see.
Mort Kunstler's cover for the July 1954 issue of STAG. I'd say these whalers are in trouble, and not a lifejacket among them. These postwar men's adventure magazines were usually preoccupied with wild animals or Nazis; looking at the articles reminds you just how repressed and uptight the 1950s actually were before the Pill and general loosening-up of sexual attitudes.
An iconic artist on of the essential super-heroes through the 1950s and early 1960s. His name involves some irony.