Sy Smith has proven throughout her career that an R&B artist can be progressive while remaining firmly rooted in tradition. Foremost a singer with a vocal range spanning five octaves, Smith began an unending succession of background gigs with Whitney Houston in the late '90s, and has since worked closely with Grammy-winning trumpeter Chris Botti and Grammy-nominated group the Foreign Exchange, among dozens of other artists. After a brief period signed to a major, Smith established an independent label of her own, an outlet for compositionally solid and sonically adventurous albums including The Syberspace Social (2005), Conflict (2008), Fast and Curious (2012), and the entirely self-produced Sometimes a Rose Will Grow in Concrete (2018). She's consequently known for being a leading force in post-millennial indie soul.
Born in New York City and a native of metropolitan Washington, D.C., Sy Smith was studying piano at the age of seven and continued into her early teens. She started singing in sixth grade, performing in choirs and eventually in classical competitions, and during high school was part of a go-go band called In Tyme. After attending Howard University — where she earned a Bachelor of Science degree in psychology with a minor in music therapy — Smith relocated to Los Angeles and soon filled an assortment of touring, acting, writing, and recording roles. The year she hit the West Coast, she landed her first songwriting credits with Adina Howard's "Swerve On" and Gerald Albright's Lalah Hathaway-fronted "Live to Love," and began a long-term recurring role backing Vonda Shepard on Ally McBeal. Just as significantly, if not more so, she toured extensively with Whitney Houston, and through the next couple years also worked with the likes of Macy Gray, Ginuwine, and Brandy.
Smith made her solo debut in 1999 with an Ali Shaheed Muhammad-produced cover of Edie Brickell & New Bohemians' "What I Am," included on the soundtrack for the animated television series The PJs. Signed to that album's label of release, Hollywood, Smith issued her first single, "Gladly," later that year. It impacted Billboard's R&B/hip-hop chart, peaking the following January at number 79, and was followed with another single, "Good N Strong." Although parent album Psykosoul was shelved — despite the circulation of advance promotional copies and Billboard coverage — Smith's career nonetheless gained momentum. Her "Welcome Back (All My Soulmates)," which appeared in the televised movie Dancing in September, was nominated for a Primetime Emmy in the category of Outstanding Music and Lyrics. She and Al Green duetted on the Babyface-written theme song for the TV series version of Soul Food. Smith also busied herself with continued work on Ally McBeal and in other background capacities, such as musical director for the BET talent showcase Lyric Cafe and more soundtrack placements. In 2002, she launched her independent Psyko label with One Like Me, an EP of five songs she wrote and produced with input from a small cast including Curtis "Sauce" Wilson. During the next two years, Smith was featured prominently on Brand New Heavies' We Won't Stop and Ali Shaheed Muhammad's Shaheedullah and Stereotypes.
In 2005, Smith began a several-season run as a background singer on American Idol, having reconnected with Whitney Houston's musical director, Rickey Minor. The Syberspace Social arrived later in the year as Smith's second album. Muhammad and James Poyser took part, as did Nicolay, thereby initiating a deep affiliation with the Foreign Exchange family. Shortly thereafter, Smith gave Psykosoul a proper and expanded release as Psykosoul +. Between proper full-lengths, Smith also made featured appearances on projects from Nicolay and Meshell Ndegeocello, earned NAACP Theatre Awards nominations for her work in the stage productions If You Don't Believe: A Love Story and Body Language, joined trumpeter Chris Botti's ensemble (through cousin Mark Whitfield), and put together a live DVD entitled Worship at the Temple. All of that and more preceded the 2008 release of Conflict. Her third LP, Conflict was highlighted by "Fly Away with Me," which registered on Billboard's Hot Adult R&B Singles Airplay chart. Featured appearances on material from fellow major-label refugee/indie soul front-runner Eric Roberson, as well as Foreign Exchange associate Zo!, closed out the decade.