What does it mean to say a wine is “dry”? And which wines are driest?

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Dear Dr. Vinny,
What does it mean to say a wine is “dry”? And which wines are driest?
—Sampath, Sri Lanka
Dear Sampath,
Not everyone uses the term “dry” the same way, but for the vast majority of the wine world, a wine that is “dry” has no perceptible sweetness.
Most of the table wines we drink are dry. Winemakers use the term to indicate that the sugar from the grapes has been completely converted to alcohol during the fermentation process; if the sugar is gone, the wine is “dry.” If fermentation is incomplete and there is some leftover sugar, that residual sugar contributes sweetness, and those wines can range from “off-dry” (or semi-sweet) to very sweet dessert wines, depending on the volume of residual sugar.
Some wine lovers use the terms “dry” or “drying” to communicate how the wine’s tannins feel in their mouth, which can be confusing, as not all dry wines feel dry—many wines are technically dry but might seem lush, mouthwatering or even sweetly fruity. You have probably experienced the sensation of dryness on the finish of very tannic wines, which might also be described as a puckering or tugging sensation on the inside of your cheeks.
As far as which wine is the driest, again, most table wines have virtually no residual sugar. But depending on the balance of the wine’s acidity, alcohol and weight, the perception of dryness will change. There are so many other variables at play here—the type of grapes used, vintage variation, winemaking decisions and even the temperature and vessel the wine is served in, let alone personal preferences and tastes. Overall, bold, dense red wines like Nebbiolo, Syrah and Cabernet Sauvignon are most likely to feel the driest.
—Dr. Vinny