Randolph started playing the instrument as a church-going teenager in Orange, New Jersey, a small city just outside of Newark. He regularly attended the House of God Church, an African-American Pentecostal denomination that had been implementing steel guitars (or "Sacred Steel") in services since the '30s, with the pedal steel in particular being introduced during the '70s. Randolph learned to play by watching other steel players during church services; years later, he updated that sacred basis with a secular mix of funk and soul, giving a new multicultural facelift to an instrument that had often been associated with country music.

In early 2000, Jim Markel heard Randolph play at the Sacred Steel Convention in Florida and subsequently introduced him to his friend Gary Waldman. Together, Waldman and Markel began to manage Randolph's career, which took flight after Matt Hickey, a talent buyer at Manhattan's Bowery Ballroom, signed Randolph on as the opening act for the North Mississippi Allstars. Within a month, Randolph had graduated to the Beacon Theater, where he played alongside Medeski, Martin & Wood. Keyboardist John Medeski enjoyed Randolph's playing so much that he asked him to record an instrumental gospel/blues album with the band. The resulting record, The Word, was released in August 2001 to great critical and popular acclaim.

Randolph's own group, the Family Band, includes cousins Danyell Morgan and Marcus Randolph (bass and drums, respectively) and John Ginty (Hammond B-3 organ). The band's career began with opening gigs for a variety of blues, jazz-funk, and jam bands such as the Derek Trucks Band, Karl Denson's Tiny Universe, and Soulive; headlining gigs became the norm within a few months' time. Robert Randolph & the Family Band released Live at the Wetlands in fall 2001, capturing the band's live performance at the legendary Wetlands venue shortly before it closed. The group's studio debut, Unclassified, followed in 2003 and introduced Randolph to an even wider audience. One new fan was veteran guitarist Eric Clapton, who brought the band out on tour and appeared on Robert Randolph's third release, Colorblind, in 2006. In 2010, Randolph teamed up with producer T-Bone Burnett and released the album We Walk This Road which featured guest appearances from Ben Harper, Leon Russell, and Doyle Bramhall II. Randolph spent the better part of three years touring with the Family Band; they signed to Blue Note Records in the interim. Lickety Split appeared in 2013 with guests Trombone Shorty and Carlos Santana. ~ Ann Wickstrom