Carlos—one of those legends in their own time known by a single name—is not technically a bartender. He is a waiter in formal evening wear, the bar’s arbiter of how to seat, serve and schmooze the customer. Nonetheless, he was showcased in a GQ feature on the Ritz bar and cited as a “barman” extraordinaire in a Forbes article that memorialized his famous dictate for a martini: Stir “12 times, not 11, not 13.” “When I started, people didn’t even know wine existed,” says Boston’s dean of drink servers, Carlos Villalobos, a 42-year veteran of the hotel bar at the Ritz-Carlton and its successor, the Taj.  “It all was martinis: gin martinis, with lemon peel, of course. The three-martini lunch was normal. Now everything is vodka—with olives!—and special beers. Everybody is experimenting with new drinks. Even margaritas have a last name.”

Now 68 and deflecting questions about retirement, Carlos remains trim and energetic, with deep dimples and an elegant accent from his native Chile, which he left for Boston at age 24. He interviewed with corporations like John Hancock and Bank of Boston, but ended up at the Ritz while he was waiting for word back. (The bank’s chief economist, a bar regular, later begged Carlos to come work for him. He declined.) “I had no money, and I was walking past this hotel and said, ‘I’ll give it a try.’ I asked the doorman about jobs,” Carlos recalls. “He looked down his long nose at me and said, ‘Go to the entrance through the alley.” I didn’t know anything about the Ritz-Carlton. I didn’t know how exquisite it was. I just walked into the hotel and asked for a job.”

Carlos laughs, a tad rueful. From a tender age, he had an innate pride that grew into a professional equipoise. For sure, he doesn’t take slights, from bosses or customers, but remains relentlessly engaging. “I stayed at this job because I wasn’t treated like a server. I came to know so many people, so much fun, so educated and sophisticated, who talked about such interesting things. We were ladies and gentlemen serving ladies and gentlemen. Now it’s their sons and daughters, and it’s a different story. More relaxed, but more average.”

Indeed, the Ritz bar, which opened at the end of Prohibition, was fabled for its strictures, and Carlos was often the polite enforcer. Although it attracted merchant princes, celebrities and advertising and media moguls, well into the ’90s guest were forbidden to table hop or send a drink to someone at another table. Unescorted women weren’t allowed inside until 1970. There were no jeans, no sneakers, no caps; men had to wear a tie and jacket (which Carlos would happily provide from the bar’s stash). The insistence on ties was relaxed in the late ’80s, to the distress of most regulars—even the man who was once told he had to leave because his son wasn’t wearing a tie. (“Of course he isn’t. He’s 3,” the man initially protested.) The jeans and sneakers ban was dropped in 1995 with the influx of foreign tourists wearing “dungarees that cost more than suits,” as one Ritz veteran said.

The house rules led to some of Carlos’ most memorable moments. “I had to refuse to let Michael Caine in. He was impeccably dressed but wearing jeans. Pressed and perfect, but jeans. Not allowed. When I asked him to leave, he almost lost it. But he recovered and left. I felt so bad,” he recalls.

Then there was the occasion a few years ago when Matt Damon came in wearing a baseball cap. “I had to say, ‘I can’t sit you,’” Carlos says. “I asked him to remove it. He hesitated and we started talking, and he learned I had a daughter, a fan. He asked me for a piece of paper and wrote a note to her that said he met me and wished the best for her.” Then he removed his cap and sat down.

Beyond attire, Carlos says, changed habits include calls for fancy-pants spirits instead of the noble “Scotch on the rocks,” lots of beer and a more diverse clientele. Atavistic gender restrictions had ebbed by the time George Clooney came in a few years ago, accompanied by six or seven women. “He was the only man,” says Carlos, who served them. “He came up to the bar to order and was really charming. Such charisma. We talked one on one, and I want to tell you, I was impressed.” But Carlos, a model of discretion, just “can’t remember” what they said. From neckties and highballs to flannel and elderflower liqueur, bar trends change, but old standards like keeping confidences still apply. And Carlos carries on.