Mark Twain reputedly said that “too much of anything is bad, but too much of good whisky is barely enough.” Twain imported his good whisky from Scotland, whose product has been growing in popularity since. These days it is the prize of the blustery island—single malt—that has attracted a devoted following, particularly among young bon vivants like Michael Simonetti. I met Simonetti at the Brandy Library, a mahogany palace in Tribeca that overflows with jazz, beautiful people, and spirits enough to justify the Alexandrian sobriquet.

Simonetti, who works in investment banking, forged his expertise in single malts at the Library, where he unwound after late nights at work. “My discretionary income is spent on food and wine and liquor now,” he says. Indeed, his knowledge of single malts is compendious, and he discourses effortlessly on their every aspect. He touches on the origin of regional scotches in tax law, the chemical composition of single malt, and the myriad unseen factors that paint its complex smoky flavor.

Ethan Kelly, the brilliant spirits sommelier at the bar, calls Simonetti part of a trend; “the better scotches are getting much more popular,” he says. Part of that is conspicuous consumption, but it’s also a function of education. “America’s palate has developed amazingly in the last 10 years,” says Simonetti, whose girlfriend and flush coworkers are also scotch drinkers, though he admits to being “probably the most obsessed” of his group. Tonight we’re trying some of the spirits that stimulate that obsession.

The first offering is a 27-year-old Dallas Dhu, and the procedure begins with a long inhalation, the glass at an angle, the smeller’s mouth slightly open. The Dallas Dhu is strong—almost 120 proof—and fiery, partly a result of its being finished in a rum barrel (here Simonetti offers a brief primer on Scotland’s history of trade with Spain). It’s his first time tasting it, and he gets “mint and white pepper” in the nose, and a viscous, heavy-bodied mouth feel (again, the rum). Dallas Dhu is a Speyside whisky, from a region in the central Highlands rich with popular distilleries. This distillery has closed; its plant is now a museum and its product a collectors’ item. As good as the Speysides are, Simonetti is eager to migrate to his favorite region, the southern coastal Islay (pronounced eye-luh). Bunnahabhain’s 25-year-old 1979 cask strength is “one of the lighter Islays” but also, Simonetti says, “one of the perfect things.” The custom is to smell and taste both before and after adding the most wee dab of water, which renders the clear Bunnahabhain a swampy color. The deep briny flavor of the island complements the aldehydes, lanolins, and phenols that Simonetti calls the “bass notes of the whisky.”

The standout of the evening is one of the most renowned Islays, the Springbank 1969. Fame does not come cheap—it can run as high as $150 a glass. Simonetti calls it “one of the most perfect whiskies I’ve ever tasted,” but admits it’s a rare splurge. It’s supposed to have a complex nose of “candy, heather, minerals, herbs, and moss.” My novice organ picks up mainly the salt—the subtle, briny quality of caviar. Kelly stresses the balance it achieves between smell, mouth feel, and finish, the principle virtue of scotch. Simonetti draws an analogy to music: The Springbank is full of “all-star talents, but they all play together.”

Laphroiag, a northern Highlands distillery, makes a popular 10-year-old, which we pass over for a 30-year-old copper-colored scotch that Simonetti is distressed to hear Laphroiag will soon discontinue. It begins with smoke and subsides to a powerful salt, a vestige of the distillery’s proximity to the water. The “nose, the palate, and the finish are balanced and tell a story,” Simonetti says sententiously.

Finally we move to Port Ellen 1978, which Simonetti has brought along. It’s a strong—“not the most intense, but up there”—peaty Islay that “finishes like fireworks,” because (as Kelly reminds us) of its sulfurous origin. It’s not cheap, but it serves as a reminder that price does not necessarily correlate with quality; Simonetti even praises the much-maligned Ardbeg (which he describes as “iodine and medicine and a kick in the ass”) as good for novices.

By the end of our sixth glass, our conversation is swimming a little, and we come back to the Springbank, its benevolent character lingering memorably. “Frank Sinatra said there was one guy with a perfect voice, and no one ever heard of him,” Simonetti says. “Why? It was perfect. But everyone remembers Billie Holiday’s limited range.” The Springbank is not the platonic ideal of Scotch, but it has that same superlative quality. Character is what appeals—and sometimes rankles and overwhelms—in all good things; it’s also something you can never have too much of.