Since leaving her hometown of Saratoga, Naylor has gone on to become one of jazz's hottest new acts, headlining some of the country's most famous jazz venues, including Yoshi's in Oakland, the Plush Room in San Francisco, New Orleans' Snug Harbor and New York City's Birdland. Her latest CD, Live East-West: Birdland/Yoshi's debuted at No. 28 on Billboard's jazz chart in its first week. She runs her own record label, Ruby Star Records, and she is now represented by one of entertainment's most prestigious firms, the William Morris Agency, joining artists such as Howie Day, Pat Benetar, Barry Manilow and Smokey Robinson.

But she still looks back fondly on her Saratoga roots.

When Naylor was a child, her parents, Bill and Mary Jo Vitek, who still live in Saratoga, always had jazz playing around the house. They took her to jazz concerts and musicals, often at Montalvo and the Saratoga Community Theater.

Her parents collected a lot of antique, automated musical instruments. Naylor and her sister loved to sing along to 1930s player pianos, music boxes and mechanical drums. Naylor says she had no idea the music was anything but modern.

"I didn't think this was old music, just what I liked and listened to," she says.

Throughout her school days at Sacred Heart and Archbishop Mitty High schools, Naylor performed in talent shows and musicals, as well as the Sacred Heart Gospel Choir--but she thought her love of music was just a hobby. She went on to attend West Valley College. One day, in a music appreciation class, her teacher played Sarah Vaughn singing Gershwin.

"She really made me want to explore music more," Naylor says.

Although Naylor went on to major in marketing at San Francisco State University--studies she says really help her run her record label and promote herself as an artist today--she began studying performing arts intently. She enrolled in a summer conservatory program at American Conservatory Theater in San Francisco.

"I wasn't a very good actress, that has to be said," Naylor says. However, her instructors were impressed with her voice and encouraged her to pursue singing. She began taking private lessons with renowned vocal coach Faith Winthrop. After a lesson in which she sang some of her favorite Gershwin tunes for Winthrop, Naylor says Winthrop said her apprentice could have a real career as a jazz singer.

One day, Winthrop called up Naylor and told her she wasn't able to make it to a gig singing at a furniture design expo in the city. Naylor was hesitant, but finally agreed to fill in.

"I know it was her way of pushing me out there. I'm sure she could have done the gig," Naylor says, looking back. But she's glad she did--after that, Naylor caught the bug, and began searching for more gigs. "I just started trying to find the best gigs I could." She began performing at such venues as the Ritz Carlton, Enrico's in North Beach, and even spots in the San Jose Jazz Festival. After a while, she started commuting once a month to Los Angeles and elsewhere.

In hopes of garnering a record deal, Naylor began sending out demo CDs. She got a few offers, but no deals panned out--some had undesirable terms, and others fell through due to changes in the music industry. Around 2001, many labels were merging. Some segments of labels that had made offers to Naylor were dissolved, and a few executives that Naylor had been negotiating with were no longer at their labels when all was said and done.

So--she decided to go it on her own.

Naylor put out her first two CDs--a self-titled debut in 1999 and Live at the Plush Room in 2001--on her own label, Ruby Star Records. She sold her CDs on Amazon.com and by agreeing to do free, in-store performances to convince stores to carry her albums. But in early 2003, Ryko Distribution, one of the best independent distributors around, came on board, and now Naylor's CDs are everywhere.

It didn't take long for the jazz community to embrace her. She's become known for her deep, smoky voice--which many say is reminiscent of Ella Fitzgerald, Carole King and Tracy Chapman--and came onto the scene with a style no one else had, combining classic jazz and cabaret standards with modern elements of rock, folk, pop and the singer-songwriter.

In addition to her original songs, many of which she writes with Art Khu, who plays piano and guitar with her on tour, Naylor is known for what she calls "acoustic smashing"--the singing of a jazz classic over a modern rock tune, or vice versa. In her shows, one might hear Talking Heads' "Once in a Lifetime" sung over Weather Report's "Birdland," "My Funny Valentine" sung over AC/DC's "Back in Black," or the popular standard "Black Coffee" over Led Zeppelin's "Moby Dick."

People are always asking Naylor how she and her band come up with the combinations.

"It's not formulaic, we just try a bunch of ones together and laugh about the ones that don't work," she explains. "It takes a lot to figure out which ones make sense together. Basically, they should sound good even if the listener has never heard either tune, or has only heard one but not the other."

These days, Naylor says she is looking forward to expanding Ruby Star Records. She is alone on her label's roster, but hopes to add more artists within the year--all jazz in the beginning, and eventually expanding to other genres.

She is also thrilled to perform--for the first time--in Saratoga. She recently announced three special performances with music legend Michael McDonald, including the Mountain Winery on July 28.

"I'm excited to play in front of what is a truly crossover audience," she says. "And also to play in my hometown, it's great."

Playing in her band will be Khu, Jon Evans on upright bass--who also frequently performs with Tori Amos--and Josh Jones on drums and percussion.

Naylor is certainly counting her blessings.

"I wake up each day and think, 'Wow, I can't believe I have all this,' " she says.

Not bad for a girl from Saratoga.

Visit www.jacquinaylor.com. For tickets to see Naylor with Michael McDonald at the Mountain Winery, call 408.741.2822 or visit www.mountainwinery.com.