Anathema: Defined as someone or something intensely disliked, "anathema" ranks among the top 1% of looked-up words on Merriam-Webster due to its complex pronunciation and uncommon usage.
Anemone: Even Nemo from the Pixar movie couldn't easily pronounce this word, despite living in one. If you can master the first two syllables, you're on the right track.
Antarctic: With its tricky double Cs, "Antarctic" poses a challenge for pronunciation. Similar to its counterpart, the Arctic, the southern pole often gets referred to as the "Ant-ART-tic."
Antidisestablishmentarianism: This word is famous for being one of the longest in the English language, with a total of 28 letters and 13 syllables.
Asterisk: Linguists recognize this typographical symbol as a challenge due to metathesis, where sounds or syllables are accidentally rearranged in a word.
Brewery: Discussing beer-making establishments can be challenging, especially when sober, because of the tricky middle syllable in "brewery."
Cavalry: Metathesis strikes again in the pronunciation of "cavalry," which refers to armed forces on horseback. Additionally, confusion with the place Calvary from the Bible adds to the difficulty.