New Orleans jazz singer Sasha Masakow-ski grew up in an undeniably musical family in the Crescent City, yet her choice of career was her own. “My parents never pushed me into music,” she says. “They were very hands off.” (Her father, Steve, is a jazz guitarist; her mother, Ulrike, is a classical pianist.)

But perhaps no one should be surprised that Masakowski, now 26, grew up to be a singer. “I always wanted to be Pavarotti as a child,” she admits. Instead of opera, though, Masakowski chose jazz, attending New Orleans Center for Creative Arts, the city’s public high school for the arts, and then the University of New Orleans, where she studied with Leah Chase, a noted jazz singer.

“What to me makes Sasha different is her musical fearlessness,” Chase says. “She’s pretty adventurous in the music that she’ll try, and she excels in all of them. … She’s a fabulous performer.”

Masakowski’s also a busy one. “New Orleans is a performance-based city,” she says. “Performing is mostly the way you will earn your living.” In addition to fronting Musical Playground, an eclectic contemporary jazz band that blends the sound of New Orleans and Brazil, she leads the Sidewalk Strutters, which is a more traditional New Orleans-style jazz band.

Finally, she sings with Nova NOLA, a contemporary jazz band founded to celebrate the city’s post-Katrina revival. Her colleagues in Nova NOLA include her father and brother, who plays bass in addition to composing and arranging music. “I’m always learning from my father,” says Masakowski, who also loves performing with her sibling. “My brother and I have an amazing musical chemistry. It’s really, really fun, and it’s a really heartfelt experience.”

But the young musician knows that her continued success will require more than just great performances. “You have to consider it a business,” says Masakowski, who also can be found on social media such as Twitter (@sashamasakowski) and Facebook. “I spend five to six hours a day reading music, writing music, practicing and handling the business.”

She’s captured her work on two CDs so far — “Musical Playground” in 2007 and “Wishes” in 2011. “I try to record once a year in some sort of fashion,” she says. “You need to document what you’re doing.”

That’s particularly important for Masakowski, who takes the jazz traditions of musical experimentation and improvisation seriously. “As a musician, you’re constantly evolving,” she says. “You outgrow things very fast.” Her former teacher agrees. “If you’re stagnating, then you’re not doing what you need to, jazz-wise,” Chase says.

Of course, the challenge is bringing your fans along with you on that creative journey, which can be a risk, financially and critically, for a musician. But Masakowski sounds as if she can handle it. “You hope that what people enjoy about your work is the honesty and the truth that lies within.”


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  • Sasha Masakowski

    Who: New Orleans native and jazz singer who performs regularly at Hotel Monteleone’s Carousel Lounge, the Hermes Bar at Antoine’s Restaurant and other venues. Plays with multiple bands, including Musical Playground, Sidewalk Strutters and Nova NOLA.

    Notable: Daughter of jazz guitarist Steve Masakowski and classical pianist Ulrike Masakowski. Sister of bassist, composer and arranger Martin Masakowski.