Sherry over at Everything Language and Grammar had a post way back in May about some athlete who committed a venial grammar sin. Specifically, the athlete said that he had made “the stupidest mistake.” (Having made a number of gallingly stupid mistakes in my life, I can only imagine the depth of idiocy to which the stupidest mistake would descend.) Sherry claims that the athlete has made a further mistake by describing the mistake as stupidest rather than most stupid.
However, there’s no reason to suspect that stupidest is any less proper of a formation than most stupid. Personally, I prefer the former. I did a Google Books search (full view only, so as to eliminate the modern journals that were sneaking into the results) comparing use of the two possibilities before 1900 (at which point the presumed stupiding of the language may have been underway). 463 for most stupid, 407 for stupidest. Similarly, 820 for more stupid, 674 for stupider. So if stupidest has ceased to be a word, it must have done so some time in the last century. And that seems unlikely, given the number of modern people who have no problem with the word.
Motivated Grammar 
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October 4, 2008 at 8:34 pm
Jonathon
Whenever someone says about some piece of usage, “Just because it’s incredibly common doesn’t mean it’s correct,” I have to ask myself just what does make something correct.
October 5, 2008 at 2:01 pm
The Ridger
But “Stupid” fits the paradigm of adjectives that take -est perfectly: bisyllabic with stress on the first syllable and not derived from a participle. Why on earth would someone object to it? Is it because it ends with a consonant? Others do, though, granted, some of them are spelled with a vowel, such as “little”; but “clever” certainly is “cleverer”.
I suppose some people really do think things fall out so neatly: 1 syllable – er; 2 ending in a vowel – er; everything else – most. But then they complain about “funner” and accept “unhappier” …
October 7, 2008 at 1:48 pm
The Ridger
I see by her argument that nothing may ever change in a language. Too bad, then, that she has embraced the rejection of case endings and verb conjugations that so degrade so-called Modern English.
October 9, 2008 at 5:18 pm
John
The blog isn’t “Literally” is it? It’s Everything Language and Grammar. By the writer of “Literally, the Best Language Book Ever”.
October 10, 2008 at 2:11 pm
wordwhisperer
Why is ‘stupidest’ a stupid word, then? I’d love to say I will never use it again but I kinda like it ;) and I use it all ze time, too.
November 2, 2008 at 1:16 am
Gabe
Jonathon: Thanks for putting that so nicely.
The Ridger: Thanks for putting together that concise, intelligent, and useful analysis.
John: Thanks for pointing that out. I have (at long last) corrected the link.
wordwhisperer: Thanks for continuing to use “stupider”. You’re right. There isn’t a thing wrong with it.
April 28, 2010 at 10:19 pm
Billy D
I don’t get why anyone would argue this… obviously having no life and forgetting language is for RELAYING MESSAGES FROM ONE TO ANOTHER.
If you don’t COMPREHEND or UNDERSTAND the word, “stupidest” then just shoot yourself now, please. No arguing there, you have NO LIFE AND NEED SOMETHING TO ARGUE about…. sad!
Stupidest may not be on dictionary.com, but who says they won’t add it next year? You fail at life and obviously understanding what communication and language is.
This goes to ANY technical grammar nazy LOSER!!!!!
June 18, 2013 at 1:45 pm
brouhahamama
It’s grammar ‘nazi’. I hate that I had no choice but to point that out, three years later.
July 7, 2013 at 2:40 am
Montag
@Johnathan: Adherence to predetermined rules and structure.
@The Ridger: I haven’t heard of your guidelines for the -est/-er endings, but in every example I can think of involving the -id ending, most/more is proper. E.g., most lucid, more rancid, most candid.
@Billy D: Nobody’s going to arrest you for using “stupidest”. The debate is: should we view “stupidest” as grammatically correct, though it technically isn’t, because it has become extremely popular? Such things have happened before, but in my opinion they only make the already convoluted English language even harder to master.
FYI Billy…you’re arguing about people arguing over the use of a word. That’s probably more “loser”-ish than arguing over the word itself. Just sayin’.
May 12, 2016 at 5:13 am
Nadesh Sasha
I personally don’t think such a word exists in the English Language.Most Stupid is the correct word and not Stupidest! gush it just doesn’t sound right!
October 20, 2016 at 5:17 am
Judy
Donald trump used it last night, in the last debate. So there you go.
February 4, 2017 at 5:17 am
Anique Whitehurst
Grammar Nazi not nazy or I’m missing something about world history.
April 6, 2018 at 8:08 pm
Amanda Singer
Using “Stupidest”, makes a person sound less educated than using “most stupid”.
July 9, 2019 at 6:59 pm
Diane U
Precisely Amanda singer; I agree! To my ear It simply sounds less polished.