If hypercritical means very critical, then why doesn't hypocritical mean not very critical, or less than critical? Hmm. Is it possible that the English language itself is hypocritical? Well, that might be putting it a bit too strongly, but it certainly seems illogical and unpredictable at times. Of course, as any spelling bee champion can tell you, it's all about the roots. However, hypo- in this case is not a root word, per se; it's a prefix meaning "under." So why does hypocritical basically mean two-faced, operating under a double standard, insincerely pious, etc.? The dictionary gives the origin of hypocrisy as follows: "Middle English ipocrisie, from Old French, from Late Latin hypocrisis, play-acting, pretense, from Greek hupokrisis, from hupokrinesthai, to play a part, pretend, hupo-, hypo- + krinesthai, to explain, middle voice of krinein, to decide, judge, see krei- in Indo-European roots." All right, but I still don't get the "under" part, so make of that what you will. On a related note, there appears to be another word, which sort of blends the two words under consideration here: hyperhypocrisy. Or a sort-of word, anyway, defined by Urban Dictionary as: "A complaint about hypocrisy that is itself hypocritical, because it accuses one party of hypocrisy when the other party (or the complainer) also engages in hypocrisy. Often found in political discussions, especially on message boards." I believe I am neither over- nor understating matters when I say that Hypocric* appears five times in OhioLINK (though three of those represent an apparently antiquated spelling), and 81 times in WorldCat (delimited by the dates 1900–, 29 times).
(She Is Not Drowning, or Truth Leaving the Well, by Édouard Debat-Ponsan, 1898. Truth emerges from a well escaping the clerical hypocrisy and military force of the Dreyfus affair. Courtesy of Wikimedia Commons.)