McCagg’s Final Four: diphthong (two vowel sounds in one syllable), gherkin (a type of cucumber, or the vine from which it grows), hornswoggle (a hoax, or to hoax), and kerfuffle (a disturbance).
Is there any practical use for this exercise? I see it as an entertaining vocabulary-building activity: Brainstorm any number of interesting words, whether you know their meaning or not. Subject them to match-ups, two words at a time, and select the one you favor on whatever merits—definition, euphony, or some ineffable quality (I like euphony and ineffable). Repeat until you have a winner, then resolve to learn the word’s meaning if you don’t know it already, and use it in your writing.
There are no losers in this game: The runner-up simply takes its place in line, followed by the favored term in the duel between the no. 3 and no. 4 seeds and then by the runner-up in that contest. Try to use each new front-runner as it is identified.
Organize a tournament with a circle of friends (in real life or online), a writing group, or a class. Make submissions anonymous, match them up randomly, and have the participants vote on their favorite word in each pair, which then advances to a run-off with another favored word.