While he was contributing to the New Yorker as Syd Hoff, he was also contributing to the Daily Worker and New Masses as A. Redfield — the pseudonym he adopted for his radical work, The Ruling Clawss (Daily Worker, 1935) a collection of surprisingly relevant cartoons.
posted by The Whelk on Oct 29, 2011 - 21 comments

After 107 submissions, Roger Ebert wins The New Yorker cartoon caption contest. Ebert's earlier blog about captioning. [more inside]
posted by codacorolla on Apr 26, 2011 - 103 comments

We've discussed ways to win the New Yorker caption contest for its cartoons (use "previous" to see more), but the tradition of attacking the cartooning institution continues. One long-time mocker has been the anti-caption contest, which has strict rules on how to write the worst captions. Compare this and this, and this and this, to get the idea. Now, Gawker has invited people to draw the worst possible New Yorker cartoons; here are some results. [prev and prev.]
posted by blahblahblah on Aug 2, 2007 - 20 comments

How to win the New Yorker caption contest every time. (Possibly NSFW, Previous contest discussion here, link via Feministe)
posted by XQUZYPHYR on Feb 2, 2006 - 54 comments

Pssst...Got A Good Caption For A New Yorker Cartoon? Because the winning entry in this year's caption jamboree isn't very funny. Neither are the other shortlisted suggestions. It may be up to The New Yorker's standards, but it's certainly not up to MetaFilter's...
posted by MiguelCardoso on Feb 11, 2002 - 25 comments