Connoisseur’s Corner: Montecristo No. 2 (2000)

This striking pirámide is probably the most iconic Cuban cigar in existence. Produced for decades, it never went out of style, and for good reason—the smoke continues to be a blockbuster. This particular No. 2 is 23 years old and is still full of life with a rich core of nutmeg and cinnamon notes that are both opulent and harmonious. A touch of wheat appears on the finish. It’s really a perfect blend of tobacco that’s shown excellent longevity and has truly developed with age. —Marvin R. Shanken
A skinny smoke from a time when Davidoff cigars were made in Cuba. (Cuban Davidoffs were discontinued in 1991 and relocated to the Dominican Republic.) It opens with heavy notes of orange peel and tea, then it takes on some toasted almond. The finish is all cocoa powder. Lovely, balanced, complex and not overpowering. —David Savona
This oversized, extra-dark version of Litto Gomez’s Chisel was super strong in its youth. A decade in the box has done little to temper the strength in this 54 ring gauge beast: red, black and Szechuan peppercorns combine on the palate along with leather, black cherry and a touch of tannic earth. A powerhouse smoke that refuses to bow to age. —David Savona
Unlike today’s Macanudos, this was made in Jamaica with Jamaican tobacco. These were always mild and time has made them even milder. Hints of almond, vanilla and wood are reminders of what this cigar once was, but the dusty, papery finish is a strong indication that it’s past its prime. —Gregory Mottola