The Mostest

We all know the rule that, most of the time, you can add -est to the end of an adjective to denote the extreme version of the given quality. When this sounds odd, we know to revert to simply prefixing the adjective with most instead. However, there are a lot of adjectives, and a lot of possible sentences, and a lot of people randomly generating those sentences and using the extreme adjectival form in some remarkable ways.

• Avantest

  Among the avant-garde, Myra was always the avantest.

  Edward Abbey, 'The Fool's Progress'.
• Award-winningest

  In the film club, the most decorated, tenured, award-winningest NYU film professor came to discuss how Reagonomics affected movies in the eighties like RoboCop and Videodrome.

  Taffy Brodesser-Akner, 'Fleishman is in Trouble'.
• Basicest

  In chem lab, I just do the basicest thing that I can do.

  Overheard a jaded Virginia Tech student, trudging to class.
• befuddlingest:

  I'm guessing that of all the clues that might befuddle people today, this RADIO DIAL clue will be the befuddlingest.

  Rex Parker, Rex Parker Does the NYT Crossword, 27 May 2022.
• Boomiest

  The concentrate boom is the boomiest boom since the Brazilian rubber boom.

  John McPhee, 'Oranges'.
• Buzziest:

  While not the first romance novel adaptation to hit the small screen - Sweet Magnolias, Virgin River, and Outlander are all based on romance (or at least romantic) series - Bridgerton is the buzziest.

  Norah Murphy, Slate, 21 January 2021.
• Crosswordiest:

  LAILA ALI is the crosswordiest boxer there is.

  Rex Parker, Rex Parker Does the NYT Crossword, 17 July 2021.
• Excitingest:

  "We needs must love the excitingest when we see it."

  Aldous Huxley, 'Brief Candles'.
• Flyingest:

  "Alaskans are the flyingest people under the American flag, and probably the flyingest people in the world."

  Jean Porter, 'The Flying North'.
• Frenchest:

  In what may qualify as the Frenchest exchange in modern cinema, he asks her, "Are you in love now?" and she says no. "When not in love, what do you do?" he asks. "I do nothing", she replies.

  Anthony Lane, The New Yorker, 07 May 2018.
• Ghettoest:

  "Mokhtar, I have to be honest with you. This is the ghettoest business plan I have ever seen."

  David Eggars, 'The Monk of Mokha'.
• I-est: joking form of "Important-est", given that "VIP" stands for "Very Important Person".

  Of all the company's VIP's, Bryant was the I-est.

  Jeff Wise, 'Down in the Valley', Vanity Fair, March 2021.
• New York Timesiest

  On Wednesday, The New York Times did its New York Timesiest to both sides the growing success of the Biden administration's vaccine delivery program.

  Mark Sumner, Daily KOS, 10 March 2021.
• Noirest

  Definitely recommend Carol Reed's "The Third Man" - it's got one of the < b>noirest speeches ever made on screen, courtesy of Harry Lime (played by the always redoubtable Orson Welles).

  Rex Parker, Rex Parker Does the NYT Crossword, 17 February 2023.
• Shackiest

  I wasn't sure which of the run-down houses was Delicia's, but I assumed it was the shackiest.

  David Sedaris, 'Let's Explore Diabetes with Owls'
• Strenuousest

  Cooley, whom the paper described as "the strenuousest of the strenuous," and four other members of the faux cabinet were so close to the president that they advised Roosevelt on matters ranging from statecraft to spelling, and were the influential force behind adding "In God We Trust" to American coins. [The last statement is false; the motto appeared on a coin in 1864.]

  Daniel Stone, (who does not check his "facts"), 'The Food Explorer'.
• Thuddiest

  It's such a thud. Not as bad a thud as ONE EGG, but a thud nonetheless (11D: Brownie mix add-in, often). Thuddier, thuddiest, in fact, was WORSE TO COME, for which I can't even imagine a scenario (23D: Prognosis that a problem has only just begun).

  Rex Parker, 'Rex Parker Does the NYT Crossword', 21 May 2021.