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Jacqui Naylor is not an easy artist to categorize. There are times when she performs straight-ahead vocal jazz, but at other times she favors more of a folk-rock/adult alternative approach. Depending on the mood she is in at a given moment, the northern Californian can bring to mind anyone from Cassandra Wilson or British jazz vocalist Claire Martin to Sarah McLachlan or Shawn Colvin — she is as comfortable among jazz improvisers as she is in the singer/songwriter world. During one of her live performances, Naylor has no problem singing smoky jazz one minute and folk-rock or adult alternative the next — and there are times when she blurs the line between the two.
Naylor, who is very jazz-friendly but far from a rigid jazz purist, brings a long list of influences to her introspective work — influences ranging from Billie Holiday, June Christy, and Nina Simone to Tracy Chapman, Natalie Merchant, Carole King, and Sheryl Crow. That is an unlikely combination of influences, certainly, but it is one that works well for Naylor (who has used all of them to fashion a personal, recognizable style of her own). Naylor has a highly diverse repertoire; on-stage, she is likely to perform a Tin Pan Alley standard right after something by the Rolling Stones or Talking Heads (in addition to performing songs of her own). Naylor is not an overly aggressive or forceful type of singer; she favors subtlety, restraint, and understatement, which are things that Holiday and Christy (one of the goddesses of jazz's cool school) were both masters of.
Born and raised in Saratoga, CA, Naylor attended San Francisco State University after graduating from high school in the '80s. Naylor entered that college to study marketing, but along the way she became interested in drama and acting — and after hearing the album Sarah Vaughan Sings George Gershwin in a music appreciation class, Naylor became seriously interested in vocal jazz. However, she continued to study marketing and earned a marketing degree from SFSU in 1991. After graduating, she spent six years as the marketing director for the well-known clothing designer Lat Naylor (her husband). But she studied music on the side, and from 1991-1995, she studied with the San Francisco-based jazz vocal teacher Faith Winthrop.
In 1996, Naylor's work in clothing design required her to spend a year in New York City, where she studied vocals on the side with Shirley Calloway (mother of cabaret/traditional pop singer Ann Hampton Calloway). Naylor returned to northern California in 1997 — and at that point, she gave up the clothing business and made music her primary focus. Naylor became a recording artist in the late '90s, recording her self-titled debut album in 1998 and releasing it on her own independent label, Ruby Star Records, the following year. She went on to record several more Ruby Star releases in the 2000s, including Live at the Plush Room in 2001, Shelter in 2003, and the two-CD set Live East/West: Birdland/Yoshi's in 2003 and 2004.