A small pour of mezcal greets many patrons at Chicano Nuevo (opens in new tab), a pop-up turned restaurant in Bernal Heights, landing on the bar practically before customers sit down. For co-owner Abraham Nuñez, giving away an ounce of artisanal Divino Maguey in a small cup, or copita, is a ritual of welcome.
“Little, tiny half-shots of something — even a half ounce of mezcal — are a way to say, ‘Hey, I like you,’” he says. “It’s a sign of affection or affinity.”
Although they’re often (but not always) thrown back in one sip, these celebratory little pours aren’t shots; they’re cheekies. And in post-pandemic San Francisco, they’re another sign of a shift away from hard partying toward more mature drinking habits. Think of the cheeky as a shot that grew up, less a vehicle for intoxication than a gesture of camaraderie.
An only-in-San Francisco origin story
Accounts differ on just how and where the cheeky originated. Some bar pros say the trend started in Latin America, with “cheeky” an anglicized version of “chiquito,” Spanish for “little.” That’s how Nuñez, a longtime fixture in the San Francisco bar scene, sees it — and he spells it “chiqui.”
At Loló (opens in new tab), a Jaliscan-Californian restaurant that may pour 80 cheekies of mezcal on a busy night, co-owner and Guadalajara native Leon Vazquez believes Nuñez might have it backward. “The first time I heard about it was when I moved [to the states],” Vazquez says. He suggests that Americans who travel and buy second homes in Mexico introduced the cheeky to his native country.
Brian Sheehy, CEO of Future Bars (opens in new tab) — the group that operates a dozen San Francisco nightlife spots, including Bourbon & Branch, Pagan Idol, and Long Weekend — claims that cheekies actually came from his own bar. Shortly after Bourbon & Branch made its splashy 2006 debut, bartenders from the nearby Irish Bank would offer the staff little nips of Fernet as a professional courtesy. They returned the favor, and a culture of reciprocity developed. The cheeky was born.
At first, Sheehy chalked this a tacit form of employee theft up to another cost of doing business in San Francisco. “It was fine in the 2000s when it was Fernet, which was inexpensive,” he says. But soon his staff alighted upon mezcal, a pricier, niche product at the time. Their use of copitas — which, because they’re made of ceramic, are opaque — disguised what everyone was doing.
Braulio Ponce, bartender at Loló, pours a round of mezcal cheekies.
Within a month, the real cost of the cheeky explosion showed up in the accounting. “We had paid for two cases of mezcal but only charged for two bottles,” Sheehy recalls. He did his best to rein in this low-level embezzlement. In return, some employees took to calling cheekies “Sheehys.”
But the genie was out of the 1.75-liter bottle. Two decades on, Sheehy has found peace with the practice — which is no longer solely his problem. “It’s a neat thing that could only start in San Francisco,” he says. “But I should have free cheekies at any bar I go to for the rest of my life.”
One rule: You have to toast it
To Colleen Downey of Trick Dog (opens in new tab), cheekies are the new “bartender’s handshake,” eating into the dominance of the Fernet shot.
Cheekies can be any kind of spirit; there are almost no rules over what is suitable. Mezcal and lower-proof amaros are the most common, but tequila and even vodka aren’t unheard of. Strictly speaking, they don’t have to contain alcohol at all. “I don’t care what it is,” says Gillian Fitzgerald of Irish bar Casements (opens in new tab). “Anyone who’s not drinking can still have a cheeky of ginger beer or soda water. It doesn’t matter.”
They can even become foundational to a place’s identity. At Lillie Coit’s (opens in new tab), a new North Beach hangout that does a brisk late-night business, owner Nick Floulis offers “welcome splashes” of sparkling wine and cheekies of Montenegro, an approachable, sweet-tasting amaro, to almost everyone. “I’m like, ‘We don’t do shots around here. This is a cheeky,’” he says. “You don’t have to drink it, but you do have to toast it.”
All four wells at Lillie Coit’s wraparound bar are stocked with a bottle of Montenegro, Floulis says. On Saturday nights, they’ll go through six or more 1-liter bottles. “I refuse to send a cheeky out in a nonfrozen glass,” he says, adding that the Formica bar top allows him to frictionlessly slide one toward patrons. “It’s our little gift across the bar.”
Apart from their diminutive size, cheekies’ other defining characteristic is that they must be offered by staff. If customers try to order one, they’re effectively wheedling free booze — a cheeky move, indeed.
Tallboy, a “martini dive bar” in Oakland’s Temescal neighborhood, found a workaround: selling cheekies for $3 each. A section of its menu (opens in new tab) comprises six chilled, 1-ounce mini-cocktails — including a Fernet-and-Coke and a “teeny-tini” — kept in a top-loading freezer for easy access.
“When a cheeky is really doing its best, it’s turning something on its ear a little bit,” owner Den Stephens says. “It has to be fun.” He wanted something crafted by the house to demonstrate execution and technique, but without making people commit to a full cocktail. A cheeky, he says, is “a petite little moment: an ‘amuse-booze.’”