Many philosophers have on their shelves a copy of Philosophers, the 1993 book of photographs of philosophers with the famous photograph of Anscombe and Geach on the cover. Steve Pyke, the creator of that work, is now a staff photographer for the New Yorker. In the ensuing years, he has continued the project, and has just posted on his website not only 25 pictures from the original book, but also 25 newer photos of what are by and large somewhat friendlier looking philosophers.
UPDATE: Pyke has taken many more photos of philosophers; what is now posted on his website is only a randam sampling of what I can only assume must be the best looking ones.
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