Dave Ricketts remembers a time, not long ago, when the clerks at his local music store referred to gypsy jazz as “fag music.” 


Now he says those same guys hit him up for advice about which guitar strings bring out the best gypsy jazz sound. 


Ricketts formed the Gaucho Gypsy Jazz Band about 10 years ago following a three-year stint in Hot Club of San Francisco. Gaucho promptly began unleashing wildly entertaining live instrumental shows fueled by the group’s intermingling playfulness and musicianship – and led by Ricketts’ unblemished and intricate fluidity on guitar. 


Their tight-knit 1930s Eastern European standards, Reinhardt covers, swing hits and New Orleans jams enabled the outfit to make a name for itself around S.F., scoring high-profile fans like Joy Luck Club author Amy Tan.


Though already polished and established, Gaucho reinvented itself a few years back. Ricketts was going through a painful divorce and felt inspired to start writing his own material. (Previously the band hadn’t performed originals.) 


“Music is such a personal experience,” Ricketts says. “It comes from having rough experiences, like a divorce. It was a great way to stay focused instead of getting caught up in the bad stuff.”


Ricketts’ fiery flurry of songwriting resulted in Pearl. The album features 10 original tracks and New York City-based vocalist Tamar Korn, who will join the Gaucho Gypsy Jazz Band Trio on Friday night at the Museum of Monterey – which has undergone a reinvention itself – along with Rob Reich on accordion and Ari Munkres on standup bass.


Korn gives life to Ricketts’ beautifully bleak break-up lyrics on Pearl’s title track. She delivers each line as if she lived through the heartbreak herself. Her vintage vibrato oozes with the same kind of savory antique lure that soaks the accompanying instrumental parts.


“There’s no one out there like [Korn],” Ricketts says. “She’s a world-class vocalist and charming performer.”


Ricketts never imagined that the vocal role on Gaucho’s most recent release, Part-Time Sweetheart, would go to one of his former music pupils, but sure enough there’s 20-year-old Georgia English, who took guitar lessons from him for six years beginning at 8 and now studies songwriting and voice at Berklee School of Music in Boston. 


“You’re hoping just to encourage [students] to like music and then go back to skateboarding,” he says. “I’ve been teaching for 15 years and it’s rare that you get to see something like this.”


On Sweetheart, the title track opens with Ricketts’ one-minute, romantic guitar serenade constructed from semitones, appoggiaturas and mordents. Then he creeps into gypsy jazz strums and gives way to English’s invigorating blend of modern and retro, an amalgamation that fits nicely with Gaucho’s dedication to old-world sound and Ricketts’ openness to trying new things.