Your initial perception of Dos Jefes may depend on how you get there.
You may take the streetcar along St. Charles Avenue, through the Garden District and Uptown, passing glorious mansions on either side, then descending at Joseph Street, and finally strolling with a cigar toward the Mississippi River. The houses will get smaller (and arguably more charming), and the air will get thicker. You'll walk past banana trees and palm trees, and wave to people on their porches, people who have lived in these shotgun houses—some elegant, some in captivating disrepair—all their lives.
Or maybe you'll drive along Tchoupitoulas Street, a largely industrial strip lined with warehouses and wharves where boats from all over the world stop to load and unload their cargo, as they've done since the Spanish and French settled this swampy region centuries ago.
Dos Jefes sits on the corner of these two worlds.
Step on in. This place is more like a hangout than a chichi cigar bar, with velveteen recliners and a sofa sharing space with a diner booth, Formica-topped tables and an old church pew. Two wooden Indian chiefs, the dos jefes for which the place is named, keep an eye on the action, one wearing sunglasses like the bust of Professor Longhair over at Tipitina's. The place seems to have been furnished by a couple of guys who pitched in their favorite furniture, novelty lamps and movie posters of actors with stogies—all the stuff their wives had relegated to the attic. (No basements at three feet below sea level.)
Still, nothing could be more New Orleanian. Ceiling fans spin overhead, as they do in nearly every New Orleans home. A stuffed fish arches above the bar, and near the jukebox sit three video poker machines, which have cropped up in seemingly every watering hole since gaming was legalized in New Orleans in the mid '90s.
The crowd reflects the easygoing mix of ages and walks of life that the natives take for granted. "About 75 percent of our customers live within two miles," says owner Shawn Stallard, who opened the joint with his partner Ritchie Shaner, in 1996, following up on the success of their eponymous cigar store, opened a few blocks away in 1994. Old neighborhood eccentrics sit at the bar aside workers, a young couple with their Boston terrier, and graduate students from Tulane and Loyola universities. They come for smokes, conversation, pool and nightly live music. "We never have a cover charge," says Stallard. "We have too many regulars. Dos Jefes is the best free show since Mardi Gras."
A glass humidor to the left of the bar displays about 40 brands of smokes available in a wide range of sizes and prices. There's no cigar menu, because Stallard and Shaner rotate the selection between the bar and the shop. Believe it or not, the cigars here are priced at or just above the store prices—making them a downright bargain. A Macanudo Portofino goes for $7.50 and an H. Upmann Churchill for $6.75. Most of the cigars fall between $6 and $10. The most expensive choice is the Partagas 150 A at $40, which wound up here after a successful run at the store, where guys gather on Sundays and Mondays for cigars and televised football.
New Orleans is steamy, even at night, but a rum or whiskey drink offsets the heat. A list of 18 rums reminds you of the proximity to the Caribbean, while the men sipping Bourbon and telling stories don't let you forget this is the Deep South.
Feel like something a tad less potent? Choose from 18 wines by the glass, including Caymus Conundrum ($7.50), a Napa Valley white that's as fragrant and heavy as the air outside, and Heitz Zinfandel ($6.50), also from Napa, a spicy, dark red that stands up nicely to a full-bodied smoke from Honduras or Nicaragua. Then again, sometimes a beer hits the spot. I recommend the Abita Turbo Dog ($3.50), a local microbrew made across Lake Pontchartrain in Abita Springs, Louisiana. The Dog is my favorite, but if you prefer something a little less stout, go with Abita Amber or even Dixie, an underrated light lager that always wins with fried seafood. Both are a steal at $2.25.
Speaking of food, the menu's scribbled on the chalkboard above the bar. You might munch on fries or nachos, or go a little upscale with a pesto tart, shrimp toast or baked brie. Whether you graze or gorge, snacks range from $3 to $7. If they are available, order the oysters meuniere ($6.00). Even in this city renowned for its seafood, these crisp, meaty tidbits stand out as delicacies. A ribeye steak sandwich ($7.50) satisfies heartier appetites.
Some come to Dos Jefes for the music. Young men shake their heads to jazz or bebop, entranced by the energy of the Webster Davis Bebop quartet, for example, which plays here often. Other folks prefer to sit outside on the patio, a south Florida-style haven with hanging hammock chairs and a bar surrounded with swings instead of stools. A tropical mural by Mississippi artist Tazewell Morton features fish and other underwater creatures smoking stogies beneath the waves, a kind of cigar-friendly Octopus's Garden.
Smoking, drinking and relaxing, all stigma-free. And you wonder why they call New Orleans the Big Easy? Unlike so many cigar bars in America's more frenetic cities, Dos Jefes isn't an escape from real life. It is real life.
Angel Antin is a Denver-based freelance writer whose roots and heart are in New Orleans.
Dos Jefes Uptown Cigar Bar
5535 Tchoupitoulas St. (corner, Tchoupitoulas and Joseph)
New Orleans, Louisiana 70115
Daily, 5 p.m. until late (sometimes as late as 5 a.m.)