More often than not, the cigar, like most things in life, is best enjoyed in moderation. Hence the proliferation of the more reasonable sizes, your coronas and bullets and robustos. These, smoked at a slow pace, last for 45 minutes to an hour before your fingertips and tongue begin to singe. But there is an argument to be made, despite the jokes about compensating for something and the warnings about making yourself sick, for the enormous cigar.

There is no one proper size for the “big” cigar. Mostly, “big” means anything over six inches long and above a 56 “ring gauge,” or diameter by the 1/64 of an inch. This includes the Churchill, the most iconic of the bunch, smoked in boatloads by the larger-than-life man from which it gained its name; he dipped his in cognac (feel free to try it, though most cigar aficionados turn up their noses at the practice). There is the double corona, so long that you can sight down it like a rifle when you put it in your mouth; the figurado, which grows and then tapers like the hips of a curvy woman; and the toro grande, which is out-and-out humongous. Smoked leisurely — as they should be — these big cigars last between two and three and a half hours.

The best-kept secret about the big cigar is that it is one of the most effective excuses to loaf in the world. This can be done with a good companion over healthy conversation, politics or philosophy or literary history, the sort of stuff that requires time. The other alternative is to do it on your own, with a reserve of something to sip and a good book.

In fact, the longest of cigars pairs perfectly with the shortest of books. Poe defined the short story as enabling the author “to carry out his full design without interruption. During the hour of perusal, the soul of the reader is at the writer’s control.” This is also true of some of the best masterpieces of literature, novellas; and the journey of a long cigar, from cool sweet smoke to complete flavor in the middle and robust spice at the end, follows the same sort of plot path as a great book of under 150 pages.

So, as spring unfolds into sunny afternoons, I say you should take a half day, find a cozy spot, light up and crack a novella. Don’t forget enough drink to last you. Below are three pairing options to do just that.

The Rare Books


The Strand’s Rare Book Room, located on the third floor of New York’s big, well-loved book store, is filled with rare gems. For this piece, they provided us with three rare first-edition copies of novellas from great American writers.

Romeo y Julieta Reserva Real Magnum and ‘The Old Man and the Sea’

Nearly Cuban


A Connecticut-shade wrapper makes for a smooth, creamy smoke. This serves the Reserva Real Magnum just fine: even with its medium-bodied Dominican and Nicaraguan filler, it’s one of the most approachable big cigars you can find. It also gives it the round, pleasant subtlety so beloved of Cuban cigars. Pair it with The Old Man and the Sea, Hemingway’s late-life masterpiece, and a bright silver rum on the rocks from a distillery that, during Papa’s time, was still making rum in Cuba.

Cigar: Romeo y Julieta Reserva Real Magnum $8
Novella: The Old Man and the Sea $850
Drink: Bacardi Facundo Neo Silver Rum ($40+) in a Kaufmann Mercantile copper flask $299

Davidoff Royal Series Salomone and ‘The Crying of Lot 49’

The Heavy Stuff


Thomas Pynchon is known for his dense prose; the Davidoff Royal Series packs a punch, too. And while the subject of The Crying of Lot 49 is a mythical underground postal service, the Salomone — and its eight-and-a-quarter inches of aged Dominican filler leaf — is very palpably real. Grady’s cold brew sipped over ice will keep you from succumbing to a nap from its potency. Enjoy both slowly while you try to decipher sentences like “The reality is in this head. Mine. I’m the projector at the planetarium, all the closed little universe visible in the circle of that stage is coming out of my mouth, eyes, and sometimes other orifices also.”

Cigar: Davidoff Royal Series Salomone $54
Novella: The Crying of Lot 49 $250
Drink: Grady’s Cold Brew Concentrate $10 (8-ounce bottle)

Montecristo Relentless Churchill and ‘Death of a Salesman’

Setting the Stage


Churchill loved his theater. (Rumor has it the old asshole would go to Shakespeare and recite the whole play alongside the actors.) And while Arthur Miller’s Death of a Salesman isn’t technically a novella, its tragedy reads quickly and well in print form. The Ecuadorian CT shade wrapper and Nicaraguan and Brazilian filler of the Montecristo Relentless Churchill should pair well with the funky, dark complexity of North Coast Brewing’s Brother Thelonious Belgian-style abbey ale.

Cigar: Montecristo Relentless Churchill $13
Novella: Death of a Salesman $175
Drink: North Coast Brewing Brother Thelonious $11+