When it came down to the critical moment, Bill Santiago decided to trade headlines for punch lines.

After establishing himself at Puerto Rico’s San Juan Star and contributing features to the Washington Post, Santiago gave up a burgeoning career as a free-lance journalist two years ago to pursue his passion for stand-up comedy. Looking for the best place to work his way up the stand-up ladder, he settled in San Francisco, a city with a long tradition of sharp, edgy comedians.

“What made it the perfect time was that it was absolutely the wrong time to do it, because my journalism career had never been better,” Santiago said during lunch at a waterfront restaurant on the Embarcadero.

“But I was having literal nightmares about not doing stand up. I liked writing. Even today I would be happy disappearing in South American and just writing. But this is a calling.”

After paying dues at countless open-mike nights at Cobb’s and the Punchline, Santiago, 29, has graduated to one-man shows, where his high-octane performances have gained him a dedicated coterie of supporters. Mixing the verbal dexterity of George Carlin, the amorous self-deprecation of Woody Allen and the physical presence of Michael Richard’s Kramer on “Seinfeld,” Santiago is both a keen observer of human relationships and a quick-eared dissector of 20th-century euphemism (“The stock market doesn’t crash anymore. Now we have corrections. I’d hate to be in a plane correction.”)

His latest show, “On the Verge of a Latin Meltdown,” which plays Sunday, as well as Sept. 19 and 26 at Venue 9 in San Francisco, takes a bemused and skeptical look at the vogue of all things Latino. (On Ricky Martin: “Who would have thought all you had to do to make Latin music so popular is just take out the Latin music?”) The show features a one-hour set of Santiago’s trenchant stand-up followed by Cuban percussionist Roberto Borrell’s Orquesta La Moderna Tradición playing classic Afro-Cuban dance music.

In many ways, the show is a time trip back to the days when comedy and jazz easily shared space in nightclubs.

“I like bringing people back to the heyday of the hungry i,” Santiago said, referring to the old North Beach night spot. “Now you have a great music scene and a vibrant comedy scene and they’re separate and I love combining them. Roberto was one of the first people I met when I moved here. He’s such a genuine ambassador of Cuba. He’s into danzón and that’s it.”

Born and raised in New York by Puerto Rican parents, Santiago grew up with a group of show-business minded friends, one of whom now writes for “Politically Incorrect.” He attended film school at New York University, and dabbled in stand up, but a job at the San Juan Star, an English-language daily, brought him to Puerto Rico. Unable to suppress his zingy one-liners, he made the move to stand up after winning a prestigious national award for feature writing.

While Santiago is a captivating performer, he sees his writing as the key to success in comedy. As he’s honed his comedic talent, Santiago has taken to dissecting classic routines by comics like Carlin and Allen, much the way jazz musicians transcribe solos by Charlie Parker and Lester Young.

“I identify with Carlin’s fascination for language, the way he can take one idea and unravel it into a piece that’s enduring,” Santiago said. “Above everything else, he’s a brilliant writer. Seinfeld is the same thing, but he does it with a little bit more of a microscope and takes out the edge. There’s no politics.”

“On the Verge of a Latin Meltdown” marks the first time Santiago has worked Latino themes into a significant part of his routine. Leery of being narrowcast, he centers much of his humor on the enduring comic territory of sex and relationships. Over the years, he generated a pile of material based on his experience growing up Nuyorican, and the confluence of the hit Cuban album “Buena Vista Social Club” and Rick Martin’s “Living La Vida Loca” convinced him it was a good time to make it public.

“When I see Ricky Martin and the reaction to him, the first Puerto Rican ever on the cover of Time Magazine, you’re talking about it with your friends, your family,” Santiago said. “And you suddenly see your culture go public. It’s always been an inside thing. Suddenly it’s as if he were a Latino Internet IPO that went through the roof.”

Santiago hasn’t completely given up journalism. He’s still writing for the Washington Post and pitching the New York Times, but he’s found the freedom to express himself in comedy.

“It’s the last maverick, renegade, cowboy thing you can do,” Santiago said. “You can’t go to the School of the Americas to learn how to be a comedy mercenary. There’s no degree in it. You cannot impart wit and you cannot teach somebody to be funny.”

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