Born in New Orleans in 1986, Sasha Masakowski is the daughter of celebrated jazz guitarist Steve Masakowski and concert pianist Ulrike Antonie Sprenger. She heard jazz from an early age through her father's association with Ellis Marsalis Jr., and attended the University of New Orleans, where her father led the Jazz Studies department. She counts Bobby McFerrin, Rachelle Ferrell and Flora Purim among her influences, and performs with her father and her brother Martin — on bass — in the Masakowski Family Band.
Her debut album Wishes (Hypersoul, 2011) was recorded with pianist James Westfall; Old Green River (2015) followed with the Sidewalk Strutters, along with the electronic art-pop project Hildegard (2015) and N.O. Escape (2016) with the Masakowski Family. In February 2018 she was invited to be artist-in-residence with Denmark's national arts program JazzDanmark, collaborating with leading Danish jazz artists and touring the country for six weeks. That June she signed with Ropeadope Records and released Art Market to critical acclaim. She currently leads two bands: Art Market, New Orleans modern jazz, and Tra$h Magnolia, electronic art-rock.
She was nominated Best Female Vocalist by OffBeat magazine in 2009 and 2019 and Best Emerging Artist in 2009, named Best Emerging Artist by the Big Easy Association in 2009, and listed among Paste Magazine's 12 jazz artists to watch in 2019, with praise from Vanity Fair, DownBeat and Jazz Times. As a bandleader she has played Cotton Club Tokyo, the Blue Note and Jazz Standard in New York, Jazz at Lincoln Center Shanghai, the Detroit and Monterey Jazz Festivals, the SF Jazz Center, the Copenhagen Jazz Festival and Bird's Basement in Melbourne. During the pandemic she co-wrote and produced the experimental electronic album Quarantined with Nick with Grammy-winning trumpeter Nicholas Payton, playing weekly duo concerts livestreamed via Blue Note NYC, and later joined his New World Order trio. In 2021 she produced Thai star Rasmee's Thong Lor Cowboy — its title track, an original of Sasha's, hit No. 1 on Thai pop radio, and the album was nominated for Thai Pop Music Awards Album of the Year.